- Crossover point between dialkoxy disulfides (ROSSOR) and thionosulfites ((RO)2S=S): Prediction, synthesis, and structure
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Isomeric preference between cyclic dialkoxy disulfides and thionosulfites is governed by the ring size of the heterocycle, Rings smaller than seven atoms prefer the thionosulfite connectivity, whereas larger rings or acyclic analogues favor the unbranched dialkoxy disulfide structure, Density functional calculations were employed to predict the crossover point at which both constitutional isomers are of comparable stability. Follow-up synthesis provides the previously unknown eight-membered ring dialkoxy disulfide 14 and seven-membered ring thionosulfite 15 from the same reaction. X-ray crystallography for all but one of the reaction products and complementary NMR analysis furnishes insights into both solid-state and solution conformations, A long-standing issue regarding the concerted vs catalyzed Isomerization pathway between XSSX and X2S=S has been addressed for X = RO and shown to be acid dependent.
- Zysman-Colman, Eli,Nevins, Neysa,Eghball, Nicolas,Snyder, James P.,Harpp, David N.
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Read Online
- Synthesis and characterization of copolymers of 5,6-benzo-2-methylene-1,3-dioxepane and styrene
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Copolymerization behavior of 5,6-benzo-2-methylene-1,3-dioxepane (BMDO) with styrene (St) is studied using benzyl bromide/CuBr/1,1,4,7,7-pentamethyldiethylenetriamine radical initiating system. Structural characterization of copolymers was done using ID and 2D NMR techniques. The copolymer compositions were obtained from 1H NMR spectroscopy. The reactivity ratios for the copolymerization of BMDO with St were determined using Kelen-Tuedos method and was found to be r BMDO = 1.08 and rst = 8.53. Degradation behavior of the copolymers is also reported.
- Wickel, Holger,Agarwal, Seema
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Read Online
- RAFT/MADIX copolymerization of vinyl acetate and 5,6-benzo-2-methylene-1,3- dioxepane
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The synthesis of well-defined degradable poly(vinyl acetate) analogues is achieved by RAFT copolymerization of 5,6-benzo-2-methylene-1,3-dioxepane (BMDO) and vinyl acetate (VAc) using methyl (ethoxycarbonothioyl)sulfanyl acetate (MEA) as controlling agent. Several monomer mixtures with low BMDO contents (30 mol %) are employed to prepare different copolymers. In all the cases, the evolution of molar masses and the dispersity values (1.26) confirm the controlled feature of the polymerization. The livingness of the obtained chains is demonstrated by successful chain extension experiments with VAc, although the presence of dead chains is also shown. The introduction of ester groups into the main chain of these P(VAc-co-BMDO) copolymers allows their degradation when treated with a mixture of KOH/MeOH in reflux during 2.5 h.
- D'Ayala, Giovanna Gomez,Malinconico, Mario,Laurienzo, Paola,Tardy, Antoine,Guillaneuf, Yohann,Lansalot, Muriel,D'Agosto, Franck,Charleux, Bernadette
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Read Online
- Homopolymers and random copolymers of 5,6-benzo-2-methylene-1,3-dioxepane and methyl methacrylate: Structural characterization using 1D and 2D NMR
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Complete structural characterization of 5,6-benzo-2-methylene-1,3-dioxepane (BMDO) monomer and its homopolymer is carried out using 1D and 2D NMR techniques. Copolymers of BMDO were made with MMA under ATRP reaction conditions. The copolymer compositions were obtained from 1H NMR spectroscopy. The reactivity ratios for the copolymerization of BMDO with MMA were determined using the Kelen - Tuedos method and was found to be rBMDO - 0.53 and rMMA = 1.96. Compositional and configurational sequence analysis of copolymers is also done.
- Wickel, Holger,Agarwal, Seema,Greiner, Andreas
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Read Online
- High Efficiency Catalytic Transfer Hydrogenation of Furfural to Furfuryl Alcohol Over Metallic Oxide Catalyst
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Development of simple and high performance solid catalysts for the utilization of biomass has become an important research topic in heterogeneous catalysis and sustainable chemistry. Herein, a highly efficient catalytic system was studied for the catalytic transfer hydrogenation of furfural to high value furfuryl alcohol over a series of acidic or basic oxides catalysts. Among those oxides, acidic Al2O3 is identified as the most effective for FAL production, giving a FUR conversion as high as 40% (FUR consumption rate was 186?mmol gcat?1 h?1) and FAL selectivity of 99% after only 5?min at 150?°C using 2-propanol as the H-donor and solvent. Furthermore, the as prepared Al2O3 give an Ea value of 15.2?kJ/mol, which is much lower than other complex catalysts in the literatures. Correlating the catalyst performance with its physical and chemical properties uncovers that the large specific surface area and high acidity of Al2O3 would be the key to the catalyst performance. Graphical Abstract: [Figure not available: see fulltext.]
- Liu, Zonghui,Wen, Zhe,Xue, Bing,Zhang, Zhongze
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- Novel substituted N-benzyl(oxotriazinoindole) inhibitors of aldose reductase exploiting ALR2 unoccupied interactive pocket
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Recently we have developed novel oxotriazinoindole inhibitors (OTIs) of aldose reductase (ALR2), characterized by high efficacy and selectivity. Herein we describe novel OTI derivatives design of which is based on implementation of additional intermolecular interactions within an unoccupied pocket of the ALR2 enzyme. Four novel derivatives, OTI-(7–10), of the previously developed N-benzyl(oxotriazinoindole) inhibitor OTI-6 were synthetized and screened. All of them revealed 2 to 6 times higher ALR2 inhibitory efficacy when compared to their non-substituted lead compound OTI-6. Moreover, the most efficient ALR2 inhibitor OTI-7 (IC50 = 76 nM) possesses remarkably high inhibition selectivity (SF ≥ 1300) in relation to structurally related aldehyde reductase (ALR1). Derivatives OTI-(8–10) bearing the substituents –CONH2, –COOH and –CH2OH, possess 2–3 times lower inhibitory efficacy compared to OTI-7, but better than the reference inhibitor OTI-6. Desolvation penalty is suggested as a possible factor responsible for the drop in ALR2 inhibitory efficacy observed for derivatives OTI-(8–10) in comparison to OTI-7.
- Hlavá?, Matú?,Ková?iková, Lucia,?oltésová Prnová, Marta,Addová, Gabriela,Hanquet, Gilles,?tefek, Milan,Bohá?, Andrej
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supporting information
(2020/12/09)
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- Low-valent dialkoxytitanium(ii): a useful tool for the synthesis of functionalized seven-membered ring compounds
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Herein, we describe unprecedented access to all-carbon or heterocyclic seven-membered ring frameworks from 1,8-ene-ynes promoted by inexpensive low-valent titanium(ii) species, readily available from Ti(OiPr)4and Grignard reagent. A broad range of cycloheptane, azepane or oxepane derivatives has been obtained (19 examples) with moderate to good yields and an excellent selectivity (up to 95/5 d.r.).
- Bodinier, Florent,Sanogo, Youssouf,Ardisson, Janick,Lannou, Marie-Isabelle,Sorin, Geoffroy
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supporting information
p. 3603 - 3606
(2021/04/14)
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- A Unified Catalytic Asymmetric (4+1) and (5+1) Annulation Strategy to Access Chiral Spirooxindole-Fused Oxacycles
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A unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides has been achieved in the presence of a chiral phase-transfer catalyst (PTC). This general strategy utilizes peroxides as unique bielectrophilic four- or five-atom synthons to participate in the C?C and the subsequent umpolung C?O bond-forming reactions with one-carbon unit nucleophiles, thus providing a distinct method to access the valuable chiral spirooxindole-tetrahydrofurans and -tetrahydropyrans with good yields and high enantioselectivities under mild conditions. DFT calculations were performed to rationalize the origin of high enantioselectivity. The gram-scale syntheses and synthetic utility of the resultant products were also demonstrated.
- Gao, Min,Gong, Xiangnan,Hu, Lin,Luo, Yanshu,Xia, Yuanzhi,Xu, Qianlan,Zhao, Yukun
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supporting information
p. 19813 - 19820
(2021/08/03)
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- MODIFIED THIOXANTHONE PHOTOINITIATORS
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Latent photoinitiator compounds are described, as well as compositions containing such compounds and their uses in photoinitated methods for producing photoresist structured.
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Paragraph 0150; 0151
(2021/07/24)
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- Formal [5+1] annulation reactions of dielectrophilic peroxides: Facile access to functionalized dihydropyrans
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A general [5+1] annulation reaction, which utilized 4-bromo- or 4-mesyloxy-but-2-enyl peroxides as unique five-atom bielectrophilic synthons to participate in the C-C and the subsequent umpolung C-O bond-forming reactions with C1 nucleophiles, has been developed for the facile synthesis of 2,2-disubstituted dihydropyrans in high yields under mild basic conditions. The dihydropyrans, which are readily prepared on a gram scale by this new method, can be flexibly transformed into the biologically important tetrahydropyrans and pyranones in 1-2 steps.
- Zhong, Chen,Yin, Qi,Zhao, Yukun,Li, Qinfeng,Hu, Lin
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supporting information
p. 13189 - 13192
(2020/11/09)
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- Direct Intramolecular Aminoboration of Allenes
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Direct intramolecular aminoboration of sulfonamidoallenes was realized using BCl3 as a boron source. The reactions benefited from the interaction between BCl3 and sulfonamides and provided a variety of borylvinyl heterocycles in good isolated yields. When chiral substrates were involved in the reactions, high stereoselectivity was observed, as can be ascertained by single-crystal X-ray diffraction experiments. Derivatization of the thus-obtained borylvinyl compounds proceeded readily, and different functionalities could be obtained via oxidation, halogenation, and Suzuki coupling reactions.
- Yang, Chun-Hua,Han, Meng,Li, Wenyan,Zhu, Ningning,Sun, Zhenzhen,Wang, Junjie,Yang, Zhantao,Li, Yue-Ming
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supporting information
p. 5090 - 5093
(2020/07/15)
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- Ruthenium-catalyzed ester reductions applied to pharmaceutical intermediates
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Ruthenium pincer complexes were synthesized and used for catalytic ester reductions under mild conditions (～5 bar of hydrogen). An experimental design approach was used to optimize the conditions for yield, purity, and robustness. Evidence for the catalytically active ruthenium dihydride species is presented. Observed intermediates and side products, as well as time-course data, were used to build mechanistic insight. The optimized procedure was further demonstrated through scaled-up reductions of two pharmaceutically relevant esters, both in batch and continuous flow.
- Shaalan, Youssef,Boulton, Lee,Jamieson, Craig
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supporting information
p. 2745 - 2751
(2020/11/30)
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- Continuous-Flow Amide and Ester Reductions Using Neat Borane Dimethylsulfide Complex
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Reductions of amides and esters are of critical importance in synthetic chemistry, and there are numerous protocols for executing these transformations employing traditional batch conditions. Notably, strategies based on flow chemistry, especially for amide reductions, are much less explored. Herein, a simple process was developed in which neat borane dimethylsulfide complex (BH3?DMS) was used to reduce various esters and amides under continuous-flow conditions. Taking advantage of the solvent-free nature of the commercially available borane reagent, high substrate concentrations were realized, allowing outstanding productivity and a significant reduction in E-factors. In addition, with carefully optimized short residence times, the corresponding alcohols and amines were obtained in high selectivity and high yields. The synthetic utility of the inexpensive and easily implemented flow protocol was further corroborated by multigram-scale syntheses of pharmaceutically relevant products. Owing to its beneficial features, including low solvent and reducing agent consumption, high selectivity, simplicity, and inherent scalability, the present process demonstrates fewer environmental concerns than most typical batch reductions using metal hydrides as reducing agents.
- ?tv?s, Sándor B.,Kappe, C. Oliver
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p. 1800 - 1807
(2020/02/27)
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- Manganese catalyzed selective hydrogenation of cyclic imides to diols and amines
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Herein we report the selective hydrogenation of cyclic imides to diols and amines, homogeneously catalyzed for the first time by a complex of an earth-abundant metal, a manganese pincer complex. A plausible catalytic cycle is proposed based on informative mechanistic experiments.
- Das, Uttam Kumar,Janes, Trevor,Kumar, Amit,Milstein, David
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p. 3079 - 3082
(2020/06/19)
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- Novel bridged tetradentate fourth subgroup metal complex as well as preparation method and application thereof (by machine translation)
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The invention provides a novel bridged tetradentate fourth subgroup metal complex and a preparation method and application thereof, wherein the complex has a formula a structure, the temperature tolerance is good, and the complex can maintain very high catalytic activity under 120 °C, can obtain ultrahigh molecular weight polyethylene, and can catalyze ethylene and norbornene, 1 - hexene and 1 - octene copolymerization reaction to obtain a polymer product with high comonomer insertion rate. (by machine translation)
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Paragraph 0223-0227; 0229-0231
(2020/10/14)
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- Method for preparation of aromatic alcohol by photocatalysis of aromatic aldehyde conversion
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The invention relates to a method for preparation of aromatic alcohol by photocatalysis of aromatic aldehyde conversion. By means of a photocatalyst, under the conditions of illumination and inert gas, fatty alcohol is adopted as a proton donor for reduction reaction on aromatic aldehyde to obtain corresponding aromatic alcohol. Fatty alcohol is used as the proton donor, and light energy is used as the energy source to promote high-conversion-rate and high-selectivity synthesis of a series of aromatic alcohol compounds from aromatic aldehyde, the method has universal applicability, and is expected to realize industrial production; and the reaction process is green and environment-friendly, low in cost, easy to operate, short in reaction period, high in conversion rate and good in selectivity.
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Paragraph 0070-0072
(2020/04/17)
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- INHIBITORS OF ADENYLATE-FORMING ENZYME MENE
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Provided herein are compounds of Formula (I) and pharmaceutically acceptable salts or tautomers thereof which may inhibit adenylate-forming enzymes. Also provided are pharmaceutical compositions, kits, uses, and methods involving the inventive compounds for the treatment and/or prevention of an infectious disease (e.g., bacterial infection (e.g., tuberculosis, methicillin- resistant Staphylococcus aureus)).
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Paragraph 0393
(2020/08/22)
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- Novel clamp metal complex and application thereof
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The invention discloses a method for preparing a novel clamp-shaped complex and application of the novel clamp-shaped complex in the reaction of catalytic hydrogenation of carboxylic acid ester compounds to produce corresponding alcohols and reaction of carbon dioxide catalytic hydrogenation to form formamide compounds. Carboxylic acid esters and hydrogen as raw materials or carbon dioxide, hydrogen and amine compounds as raw materials are reacted in an organic solvent condition or a solvent-free condition in the presence of a transition metal complex as a catalyst to respectively form the corresponding alcohol compounds and/or corresponding formamide compounds. The method has the advantages of being high in reaction efficiency, good in selectivity, mild in conditions, economical, environmentally-friendly, and simple in operation, and has good promotion and application prospects.
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Paragraph 0410-0412; 0495-0498
(2019/04/26)
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- Synthesis of 1,2-phenylenedimethanols by base-promoted reduction of isobenzofuran-1(3H)-ones with silane
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An efficient method for preparation of substituted 1,2-phenylenedimethanols and aliphatic 1,4-diols that are valuable intermediates in organic synthesis, has been developed by the base-promoted reduction of isobenzofuran-1(3H)-ones and γ-lactones with silane under mild conditions. Compared with traditional procedures using stoichiometric amounts of metal hydrides and alkyl reductants, the present method avoids the use of sensitive reagents and is operationally simple and a broad variety of functional groups are tolerated.
- Liu, Bin,Zhou, Xigeng
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supporting information
p. 725 - 728
(2018/12/11)
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- Dehydroalkylative Activation of CNN- A nd PNN-Pincer Ruthenium Catalysts for Ester Hydrogenation
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Ruthenium-pincer complexes bearing CNN- A nd PNN-pincer ligands with diethyl-or diisopropylamino side groups, which have previously been reported to be active precatalysts for ester hydrogenation, undergo dehydroalkylation on heating in the presence of tricyclohexylphosphine to release ethane or propane, giving five-coordinate ruthenium(0) complexes containing a nascent imine functional group. Ethane or propane is also released under the conditions of catalytic ester hydrogenation, and time-course studies show that this release is concomitant with the onset of catalysis. A new PNN-pincer ruthenium(0)-imine complex is a highly active catalyst for ester hydrogenation at room temperature, giving up to 15500 turnovers with no added base. This complex was shown to react reversibly at room temperature with two equivalents of hydrogen to give a ruthenium(II)-dihydride complex, where the imine functionality has been hydrogenated to give a protic amine side group. These observations have potentially broad implications for the identities of catalytic intermediates in ester hydrogenation and related transformations.
- He, Tianyi,Buttner, John C.,Reynolds, Eamon F.,Pham, John,Malek, Jack C.,Keith, Jason M.,Chianese, Anthony R.
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supporting information
p. 17404 - 17413
(2019/11/03)
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- Aluminum Hydroxide Secondary Building Units in a Metal-Organic Framework Support Earth-Abundant Metal Catalysts for Broad-Scope Organic Transformations
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The intrinsic heterogeneity of alumina (Al2O3) surface presents a challenge for the development of alumina-supported single-site heterogeneous catalysts and hinders the characterization of catalytic species at the molecular level as well as the elucidation of mechanistic details of the catalytic reactions. Here we report the use of aluminum hydroxide secondary building units (SBUs) in the MIL-53(Al) metal-organic framework (MOF) with the formula Al(μ2-OH)(BDC) (BDC = 1,4-benzenedicarboxylate) as a uniform and structurally defined functional mimic of Al2O3 surface for supporting Earth-abundant metal (EAM) catalysts. The μ2-OH groups in MIL-53(Al) SBUs were readily deprotonated and metalated with CoCl2 and FeCl2 to afford MIL-53(Al)-CoCl and MIL-53(Al)-FeCl precatalysts which were characterized by powder X-ray diffraction, nitrogen sorption, elemental analysis, density functional theory, and extended X-ray fine structure spectroscopy. Activation with NaBEt3H converted MIL-53(Al)-CoCl to MIL-53(Al)-CoH which effectively catalyzed hydroboration of alkynes and nitriles and hydrosilylation of esters. X-ray photoelectron spectroscopy and X-ray absorption near-edge spectroscopy (XANES) indicated the presence of AlIII and CoII centers in MIL-53(Al)-CoH while deuterium labeling studies suggested σ-bond metathesis as a key step for the MIL-53(Al)-CoH-catalyzed addition reactions. MIL-53(Al)-FeCl competently catalyzed oxidative Csp3-H amination and Wacker-type alkene oxidation. XANES analysis revealed the oxidation of FeII to FeIII centers in the activated MIL-53(Al)-FeCl catalyst and suggested that oxidative Csp3-H amination occurs via the formation of FeIII-OtBu species by single electron transfer between FeII centers in MIL-53(Al)-FeCl and (tBuO)2 with concomitant generation of 1 equiv of tBuO· radical, C-H activation through hydrogen atom abstraction to generate alkyl radicals, protonation of FeIII-OtBu by aniline to generate MIL-53(Al)-FeIII-anilide, and finally C-N coupling between the FeIII-anilide and alkyl radical to form the Csp3-H amination product and regenerate the FeII catalyst. These highly active single-site MOF-based solid catalysts were readily recovered and reused up to five times without significant decrease in catalytic activity. This work thus demonstrates the great potential of using the aluminum hydroxide SBUs in MOFs to support EAM catalysts for important organic transformations.
- Feng, Xuanyu,Ji, Pengfei,Li, Zhe,Drake, Tasha,Oliveres, Pau,Chen, Emily Y.,Song, Yang,Wang, Cheng,Lin, Wenbin
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p. 3327 - 3337
(2019/03/26)
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- A synthetic O-methanol derivatives (by machine translation)
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The invention belongs to the technical field of chemical engineering, in particular to a synthetic O-methanol derivatives. The invention to phthalide as raw materials, alkali and under the effects of the compound silicane, through reducing the ring-opening reaction, to prepare the O-methanol. The method of the invention raw materials are easy, simple operation, strong reaction selectivity, high product yield, mild reaction conditions; synthetic mono substituted O b methanol derivatives high quality, functional group compatibility. (by machine translation)
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Paragraph 0014; 0015; 0016; 0017; 0018; 0019
(2018/10/19)
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- Structure-Function Relationship in Ester Hydrogenation Catalyzed by Ruthenium CNN-Pincer Complexes
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A series of six pincer-ruthenium complexes has been synthesized and applied in the catalytic hydrogenation of esters. The ruthenium complexes have the formula Ru(pincer)HCl(CO), where the CNN-pincer ligands feature N-heterocyclic carbene (NHC), pyridine, and dialkylamino donor groups. Through systematic variation of the steric bulk of the NHC substituent and the amine substituents, a clear structure-function relationship emerges. The most active catalysts in this series feature the bulkiest NHC substituent employed, 2,6-diisopropylphenyl. For the dialkylamino group, catalysts substituted with isopropyl or ethyl groups were the most active, while catalysts substituted with methyl groups were significantly less active. The most active catalyst discovered catalyzes the complete hydrogenation of a range of esters at loadings of 0.05-0.2 mol %.
- Le, Linh,Liu, Jiachen,He, Tianyi,Kim, Daniel,Lindley, Eric J.,Cervarich, Tia N.,Malek, Jack C.,Pham, John,Buck, Matthew R.,Chianese, Anthony R.
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supporting information
p. 3286 - 3297
(2018/09/27)
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- Cobalt Pincer Complexes for Catalytic Reduction of Carboxylic Acid Esters
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A selection of cobalt(I) and cobalt(II) pincer type complexes with different substitution patterns was tested in the catalytic reduction of carboxylic acid esters to alcohols. The cobalt pincer type complex 4 is suitable for the hydrogenation of aromatic as well as aliphatic and cyclic esters. Mechanistic investigation indicated a metal ligand cooperated reaction pathway.
- Junge, Kathrin,Wendt, Bianca,Cingolani, Andrea,Spannenberg, Anke,Wei, Zhihong,Jiao, Haijun,Beller, Matthias
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supporting information
p. 1046 - 1052
(2018/01/01)
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- PHENANTHROLINE BASED PINCER COMPLEXES USEFUL AS CATALYSTS FOR THE PREPARATION OF METHANOL FROM CARBONDIOXIDE
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The present invention relates to a novel phenonthroline based pincer complexes and process for preparation thereof. The present invention also provides a one pot process for the conversion of carbon dioxide to methanol in the presence of a molecularly defined pincer-type single-site Ru-catalyst and secondary amine. Further the present invention provides the use of phenonthroline based pincer complexes for the esterification of alcohols and hydrogenation of esters under mild conditions.
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Paragraph 0134
(2018/04/02)
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- Enantioselective Synthesis of Indolines, Benzodihydrothiophenes, and Indanes by C?H Insertion of Donor/Donor Carbenes
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We employ a single catalyst/oxidant system to enable the asymmetric syntheses of indolines, benzodihydrothiophenes, and indanes by C?H insertion of donor/donor carbenes. This methodology enables the rapid construction of densely substituted five-membered rings that form the core of many drug targets and natural products. Furthermore, oxidation of hydrazones to the corresponding diazo compounds proceeds in situ, enabling a relatively facile one- or two-pot protocol in which isolation of potentially explosive diazo alkanes is avoided. Regioselectivity studies were performed to determine the impact of sterics and electronics in donor/donor metal carbene C?H insertions to form indolines. This methodology was applied to a variety of substrates in high yield, diastereomeric, and enantiomeric ratios and to the synthesis of a patented indane estrogen receptor agonist with anti-cancer activity.
- Souza, Lucas W.,Squitieri, Richard A.,Dimirjian, Christine A.,Hodur, Blanka M.,Nickerson, Leslie A.,Penrod, Corinne N.,Cordova, Jesus,Fettinger, James C.,Shaw, Jared T.
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supporting information
p. 15213 - 15216
(2018/10/31)
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- HETEROCYCLIC COMPOUNDS WITH MICROBIOCIDAL PROPERTIES
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The present disclosure relates to a compound of Formula I, wherein the substituents T, A, W, R2, n, Z, G, Z1 and J are as defined in the description.
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Page/Page column 104
(2018/11/22)
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- Selective Hydrogenation of Cyclic Imides to Diols and Amines and Its Application in the Development of a Liquid Organic Hydrogen Carrier
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Direct hydrogenation of a broad variety of cyclic imides to diols and amines using a ruthenium catalyst is reported here. We have applied this strategy toward the development of a new liquid organic hydrogen carrier system based on the hydrogenation of bis-cyclic imide that is formed by the dehydrogenative coupling of 1,4-butanediol and ethylenediamine using a new ruthenium catalyst. The rechargeable system has a maximum gravimetric hydrogen storage capacity of 6.66 wt%.
- Kumar, Amit,Janes, Trevor,Espinosa-Jalapa, Noel Angel,Milstein, David
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supporting information
p. 7453 - 7457
(2018/06/08)
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- Modular Synthesis of Diverse Natural Product-Like Macrocycles: Discovery of Hits with Antimycobacterial Activity
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A modular synthetic approach was developed in which variation of the triplets of building blocks used enabled systematic variation of the macrocyclic scaffolds prepared. The approach was demonstrated in the synthesis of 17 diverse natural product-like macrocyclic scaffolds of varied (12–20-membered) ring size. The biological relevance of the chemical space explored was demonstrated through the discovery of a series of macrocycles with significant antimycobacterial activity.
- Dow, Mark,Marchetti, Francesco,Abrahams, Katherine A.,Vaz, Luis,Besra, Gurdyal S.,Warriner, Stuart,Nelson, Adam
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supporting information
p. 7207 - 7211
(2017/05/31)
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- A Versatile Iridium(III) Metallacycle Catalyst for the Effective Hydrosilylation of Carbonyl and Carboxylic Acid Derivatives
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A versatile iridium(III) metallacycle catalysed rapidly and selectively the reduction of a large array of challenging esters and carboxylic acids as well as various ketones and aldehydes. The reactions proceeded in high yields at room temperature by hydrosilylation followed by desilylation. Although the reactions of various aldehydes and ketones resulted exclusively in alcohols, the hydrosilylation of esters led to alcohols or ethers, depending on the type of substrate. Regarding the carboxylic acids, again the nature of the reagent controlled the outcome of the hydrosilylation reaction, either alcohols or aldehydes being formed.
- Corre, Yann,Rysak, Vincent,Trivelli, Xavier,Agbossou-Niedercorn, Francine,Michon, Christophe
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p. 4820 - 4826
(2017/09/07)
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- Preparation and isolation of isobenzofuran
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The synthesis, isolation and characterization of isobenzofuran are described in this publication. Isobenzofuran is of general interest in synthetic and physical organic chemistry because it is one of the most reactive dienes known. A number of synthetic pathways have been published which all suffer from disadvantages such as low yields and difficult purification. We present a synthetic pathway to prepare isobenzofuran in laboratory scale with high yields, from affordable, commercially available starting materials.
- Peters, Morten K.,Herges, Rainer
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supporting information
p. 2659 - 2662
(2018/01/17)
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- Bipyridine ligand ruthenium complex is carried and its preparation method and application (by machine translation)
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The invention relates to a novel bipyridine is carried ligand ruthenium complex and its preparation method and in the ester compound hydrogenation is the application of the alcohol compound in the reaction. The use of the bipyridine ligand ruthenium complex catalytic hydrogenation is carried ester compound alcohol compound method is characterized in that: in order to ester compound material in an amount of 0.001 - 0.3 μM % bipyridyl is carried ligand ruthenium complex as catalyst, adding esters compound material in an amount of 1 - 10mol % alkali, in the 25 - 100 °C and 1 - 10MPa hydrogen pressure catalytic hydrogenation under the conditions of ester compound corresponding alcohol compound. The invention of the bipyridine ligand ruthenium complex is carried is convenient to prepare, stable structure, in the ester compound in hydrogenation reaction exhibits excellent catalytic activity. This invention has overcome the ester compound or a non-homogeneous phase catalytic hydrogenation system requires high-temperature high-pressure reaction conditions and high defects of the catalyst amount, catalyst consumption is small, mild reaction conditions, the reaction selectivity is good, improves the economy and the safety of the production system. (by machine translation)
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Paragraph 0098; 0099; 0100; 0102; 0104
(2017/04/28)
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- Cooperative interplay between a flexible PNN-Ru(II) complex and a NaBH4 additive in the efficient catalytic hydrogenation of esters
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A catalyst loading of between 0.001-0.05 mol% of the PNN-bearing ruthenium(II) complex [fac-PNN]RuH(PPh3)(CO) (PNN = 8-(2-diphenylphosphinoethyl)amidotrihydroquinoline), in combination with 5 mol% NaBH4, efficiently catalyzes the hydrogenation of esters to their corresponding alcohols under mild pressures of hydrogen. Both aromatic and aliphatic esters can be converted with high values of TON or TOF achievable. Mechanistic investigations using both DFT calculations and labeling experiments highlight the cooperative role of NaBH4 in the catalysis while the catalytically active species has been established as trans-dihydride [mer-PNHN]RuH2(CO) (PNHN = 8-(2-diphenylphosphinoethyl)aminotrihydroquinoline). The stereo-structure of the PNHN-ruthenium species greatly affects the activity of the catalyst, and indeed the cis-dihydride isomer [fac-PNHN]RuH2(CO) is unable to catalyze the hydrogenation of esters until ligand reorganization occurs to give the trans isomer.
- Wang, Zheng,Chen, Xiangyang,Liu, Bo,Liu, Qing-Bin,Solan, Gregory A.,Yang, Xinzheng,Sun, Wen-Hua
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p. 1297 - 1304
(2017/05/05)
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- Direct Catalytic Hydrogenation of Simple Amides: A Highly Efficient Approach from Amides to Amines and Alcohols
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A highly chemoselective and reactive direct catalytic reduction of various amides to amines and alcohols was developed by using a tetradentate ruthenium complex. The catalytic system showed excellent activity (turnover numbers up to 19 600) and great functional group tolerance under mild reaction conditions, compared to several bidentate and tridentate ruthenium-catalyzed systems.
- Shi, Liyang,Tan, Xuefeng,Long, Jiao,Xiong, Xiong,Yang, Song,Xue, Peng,Lv, Hui,Zhang, Xumu
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supporting information
p. 546 - 548
(2017/01/18)
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- Truncated borrelidin analogues: Synthesis by sequential cross metathesis/olefination for the southern fragment and biological evaluation
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The construction of novel borrelidin analogues is reported in which the northern fragment is truncated to a simple hydroxyundecanecarboxylate and the original cyclopentanecarboxylic acid in the southern fragment is replaced with different six-membered rings. The required precursors were prepared by cross metathesis of the appropriate carbocycle-based homoallylic alcohol with crotonaldehyde followed by HWE olefination of the resulting enal with bromocyanophosphonate. The key aldehyde for intramolecular cross coupling was accessible by oxidation of the hydroxy group of the linked undecanecarboxylate unit. Grignard mediated macrocyclization finally yielded the borrelidin related products. The investigation is complemented by SAR studies and quantum-chemical calculations.
- Gündemir-Durmaz, Tülay,Schmid, Fabian,El Baz, Yana,H?usser, Annette,Schneider, Carmen,Bilitewski, Ursula,Rauhut, Guntram,Garnier, Delphine,Baro, Angelika,Laschat, Sabine
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supporting information
p. 8261 - 8269
(2016/09/09)
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- A simple, convenient, highly regioselective synthesis of isobenzofuran-1(3H)-ones (phthalides) as well as Maculalactone A & B, the Bioactive Butyrolactones
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Bacground: Among the class of oxygen heterocycles, the benzoannulated lactone (3H-isobenzofuran-1-one or phthalide) moiety is found in many natural products. Phthalides possess a wide range of biological activity e.g. (-)-Hidrastine is active at the human opioid receptor known as CCR5, while fuscinarin interferes with HIV entry into cells. Phthalides also represent an important structural subunit in numerous natural products that exhibit a wide range of biological activities, such as antispasmodic, antifungal, vasodilators, and coronary artery dilators. Except their biological activities, phthalides are also versatile starting material for the synthesis of various important organic compounds, including the key intermediates in the synthesis of functionalized naphthalenes and anthracenes, which in turn are used as synthons for tricyclic and tetra cyclic aromatic natural products. The present communication describes a simple but efficient and expedient one pot strategy for the synthesis of phthalides. Methods: Diethyl phthalate was considered initially for the cyclization strategy using different metal hydrides at variable temperatures. The reaction was carried out at-30°C with 2.5 equivalent of DIBAL-H, the phthalide was obtained in ~68% yield along with minor amount of alcohol (~10%) and the unreacted starting material (~12%). In the reaction protocol, other solvents such as tetrahydrofuran, diethyl ether, and chlorobenzene were found to be effective in cyclization at-30°C. But yield of the phthalide was observed to be less compare to CH2Cl2. Further decrease of the reaction temperature up to-78°C showed no effect on the yield of cyclized product. Use of 3 equivalent of DIBAL-H dramatically decreases the yield of the cyclized product (30%) and increased the amount of reduced product (60%). Results: The promising outcome of the above observations encouraged us to study the general scope and limitations of this protocol for the reduction of different substituted phthalides. It was found that diethyl esters of nitro-, bromo-, 4'-methyl-biphenyl-, 3'-methyl-biphenyl-, 2'-methyl-biphenyl-, biphenyl-, 4-pyrazin-2-yl-, and 4-(4-methyl-Thiazol-5-yl)-substituted phthalic acids readily underwent reduction with DIBAL-H to afford the corresponding phthalides in moderate to good yields. Conclusion: We developed a simple, convenient, one step protocol for the synthesis of isobenzofuran-1(3H)-ones (phthalides) from phthalate esters in moderate to good yields. We have also demonstrated a short and effective route to prepare two bioactive butyrolactones, viz., maculalactone A & B. In our opinion, the present approach is general in nature and could be useful to design diverse butyrolactone skeletons.
- Joardar, Soumen,Chakravorty, Santanu,Das, Sakti P.
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p. 127 - 134
(2016/03/01)
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- Coordination Chemistry of an Unsymmetrical Naphthyridine-Based Tetradentate Ligand toward Various Transition-Metal Ions
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An unsymmetrical ligand, 2-(2-pyridinyl)-7-(pyrazol-1-yl)-1,8-naphthyridine (L5) was prepared for the construction of a series of dinuclear complexes. Treatment of L5with [Ru2(μ-OAc)4Cl] followed by anion metathesis afforded [(L5)(μ-OAc)3Ru2](PF6) (3). Reaction of L5with 2 equiv. of Ni(OAc)2provided [Ni4(L5)2(μ-OH)4(CF3COO)2](CF3COO)2(5). Reaction of [Re2(CO)8(CH3CN)2] with L5in a refluxing chlorobenzene solution gave a mixture of dirhenium (6) and monorhenium (7) complexes. The monocobalt complex 8 was obtained from complexation of L5with CoCl2. These new complexes were characterized by elemental analysis and spectroscopic techniques. The structures of complexes 3, 5 and 8 were further confirmed by X-ray crystallography. Nickel complex 5 was evaluated as a catalyst for reduction reactions involving the conversion of ester functionalities into their corresponding alcohols.
- Tsai, Bing-Chen,Liu, Yi-Hung,Peng, Shie-Ming,Liu, Shiuh-Tzung
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p. 2783 - 2790
(2016/07/11)
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- Ester Hydrogenation Catalyzed by CNN-Pincer Complexes of Ruthenium
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Ruthenium complexes supported by two new CNN-pincer ligands were synthesized. Both were tested as catalysts for the hydrogenation of esters under mild conditions (105 °C, 6 bar H2). A striking dependence on ligand structure was observed, as a dimethylamino-substituted ligand gave a nearly inactive catalyst, while a diethylamino-substituted variant gave up to 980 catalytic turnovers for the hydrogenation of benzyl benzoate. This system catalyzes the hydrogenation of various substrates including ethyl, benzyl, and hexyl esters, but is surprisingly unreactive toward methyl esters. Experiments demonstrate that base-catalyzed transesterification is rapid under the reaction conditions and that methyl esters are effectively hydrogenated when benzyl alcohol is added to the reaction mixture. The reverse reaction, dehydrogenation of primary alcohols to give esters, was tested as well; up to 920 catalytic turnovers were observed for the dehydrogenation of 1-hexanol to hexyl hexanoate.
- Kim, Daniel,Le, Linh,Drance, Myles J.,Jensen, Kelsey H.,Bogdanovski, Kristijan,Cervarich, Tia N.,Barnard, Melissa G.,Pudalov, Natalie J.,Knapp, Spring Melody M.,Chianese, Anthony R.
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p. 982 - 989
(2016/05/09)
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- DUAL SITE CATALYST FOR MILD, SELECTIVE NITRILE REDUCTION
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A ruthenium bis(pyrazolyl)borate scaffold that enables cooperative reduction reactivity in which boron and ruthenium centers work in concert to effect selective nitrile reduction is provided. The pre-catalyst compound [κ3-(1-pz)2HB(N═CHCH3)]Ru(cymene)? TfO? (pz=pyrazolyl) was synthesized using readily-available materials through a straightforward route, thus making it an appealing catalyst for a number of reactions.
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Paragraph 0058
(2016/06/09)
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- MnO2/TiO2 catalyzed synthesis of coenzyme pyridoxamine-5′-phosphate analogues: 3-deoxypyridoxamine-5′-phosphate
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The highly efficient-selective synthetic route of the pyridoxal-5′-phosphate (vitamin B6, PLP) analogues: C3 substituted deoxy derivatives of pyridoxal (PL), pyridoxal-N-oxide (PLNO), pyridoxamine (PM), pyridoxamine-5′-phosphate (PMP) and pyridoxal-5′-phosphate (PLP), were developed via reduction and followed by selective oxidation in one pot using solid supported nanoparticles. The salient features of this strategy are: economic two-fold conversion, more Lewis acid sites, vacancies on the nanoparticle surfaces, and good yields of 3-deoxypyridoxal and 3-deoxypyridoxamine-5′-phosphate.
- Abbas, Sk Jahir,Ramacharyulu,Ke, Shyue-Chu
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p. 10242 - 10248
(2016/02/05)
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- Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand
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A rhodium complex, in conjunction with commercially available Ph-BPE ligand, catalyzes the branch-selective asymmetric hydroformylation of 1-alkenes and rapidly generates α-chiral aldehydes. A wide range of terminal olefins including 1-dodecene were examined, and all delivered high enantioselectivity (up to 98:2 er) as well as good branch:linear ratios (up to 15:1). (Chemical Equation Presented).
- Yu, Zhiyong,Eno, Meredith S.,Annis, Alexandra H.,Morken, James P.
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supporting information
p. 3264 - 3267
(2015/07/15)
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- Bis-N-heterocyclic Carbene Aminopincer Ligands Enable High Activity in Ru-Catalyzed Ester Hydrogenation
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Bis-N-heterocyclic carbene (NHC) aminopincer ligands were successfully applied for the first time in the catalytic hydrogenation of esters. We have isolated and characterized a well-defined catalyst precursor as a dimeric [Ru2(L)2Cl3]PF6 complex and studied its reactivity and catalytic performance. Remarkable initial activities up to 283 000 h-1 were achieved in the hydrogenation of ethyl hexanoate at only 12.5 ppm Ru loading. A wide range of aliphatic and aromatic esters can be converted with this catalyst to corresponding alcohols in near quantitative yields. The described synthetic protocol makes use of air-stable reagents available in multigram quantities, rendering the bis-NHC ligands an attractive alternative to the conventional phosphine-based systems.
- Filonenko, Georgy A.,Aguila, Mae Joanne B.,Schulpen, Erik N.,Van Putten, Robbert,Wiecko, Jelena,Müller, Christian,Lefort, Laurent,Hensen, Emiel J. M.,Pidko, Evgeny A.
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supporting information
p. 7620 - 7623
(2015/07/02)
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- Highly efficient and chemoselective zinc-catalyzed hydrosilylation of esters under mild conditions
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A mild and highly efficient catalytic hydrosilylation protocol for room-temperature ester reductions has been developed using diethylzinc as the catalyst. The methodology is operationally simple, displays high functional group tolerance and provides for a facile access to a broad range of different alcohols in excellent yields.
- Kovalenko, Oleksandr O.,Adolfsson, Hans
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supporting information
p. 2785 - 2788
(2015/02/05)
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- A General, Practical Triethylborane-Catalyzed Reduction of Carbonyl Functions to Alcohols
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A combination of the abundant and low-cost triethylborane and sodium alkoxide generates a highly efficient catalyst for reduction of esters, as well as ketones and aldehydes, to alcohols using an inexpensive hydrosilane under mild conditions. The catalyst system exhibits excellent chemoselectivity and a high level of functional group tolerance. Mechanistic studies revealed a resting state of sodium triethylalkoxylborate that is the product of the reaction of BEt3 with sodium alkoxide. This borate species reacts with hydrosilane to form NaBEt3H, which rapidly reduces esters.
- Peng, Dongjie,Zhang, Mintao,Huang, Zheng
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supporting information
p. 14737 - 14741
(2015/10/19)
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- Iron(II) pincer-catalyzed synthesis of lactones and lactams through a versatile dehydrogenative domino sequence
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The synthesis of lactones and lactams by using iron(II) pincer-catalyzed dehydrogenative methodology was developed. Starting from 1,n-diols or 1,n-amino alcohols, this domino transformation takes place through initial dehydrogenation of the substrates, subsequent intramolecular cyclization, and final oxidation to afford the desired products in good yields. The ability to access heterocycles of different sizes makes this protocol especially versatile, in which two consecutive oxidation reactions are performed without requiring an external oxidant. In this paper, we report the application of the Fe-MACHO-BH complex [carbonylhydrido(tetrahydroborato)[bis(2-diisopropylphosphinoethyl)amino]iron(II)] in this atom-efficient and environmentally benign process, for which molecular hydrogen is formed as the only stoichiometric side product. Just a little pinch: The iron(II) pincer-catalyzed synthesis of lactones and lactams from easily available 1,n-diols and 1,n-amino alcohols is explored. The use of a nontoxic metal as well as the generation of molecular hydrogen as the only stoichiometric byproduct makes this method a highly atom-efficient and environmentally benign process.
- Pea-Lpez, Miguel,Neumann, Helfried,Beller, Matthias
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p. 865 - 871
(2015/03/14)
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- A new designed hydrazine group-containing ruthenium complex used for catalytic hydrogenation of esters
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A hydrazine group-containing nitrogen-phosphine ligand and corresponding ruthenium complexes were synthesized. When these complexes were used for hydrogenation of esters, excellent performance was observed (TON up to 17 200). A wide substrate scope was suitable for this catalytic system.
- Tan, Xuefeng,Wang, Qingli,Liu, Yuanhua,Wang, Fangyuan,Lv, Hui,Zhang, Xumu
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p. 12193 - 12196
(2015/07/27)
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- Highly efficient tetradentate ruthenium catalyst for ester reduction: Especially for hydrogenation of fatty acid esters
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A new tetradentate ruthenium complex has been developed for hydrogenation of esters. The catalysts structure features a pyridinemethanamino group and three tight chelating five-membered rings. The structure character is believed to be responsible for its high stability and high carbonylation-resistant properties. Thus, this catalyst shows outstanding performance in the catalytic hydrogenation of a variety of esters, especially for fatty acid esters, which may be used in practical applications. New insight on designing hydrogenation catalyst for reducing esters to alcohols has been provided through theoretical calculations.
- Tan, Xuefeng,Wang, Yan,Liu, Yuanhua,Wang, Fangyuan,Shi, Liyang,Lee, Ka-Ho,Lin, Zhenyang,Lv, Hui,Zhang, Xumu
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supporting information
p. 454 - 457
(2015/03/05)
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- Prins spirocyclization for the synthesis of spiro[isobenzofuran-pyran] derivatives
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A Prins cascade process was developed for the synthesis of tetrahydro-3H-spiro[isobenzofuran-pyran] derivatives in good yields and selectivity by the condensation of 3-[2-(hydroxymethyl)phenyl]but-3-en-1-ols with aldehydes or ketones. The reaction proceeds smoothly in the presence of indium(III) trifluoromethanesulfonate (30 mol-%) in dichloroethane at 80 C. This is the first report on the synthesis of tetrahydro-3H-spiro[isobenzofuran- pyran] scaffolds through a Prins cascade reaction. Copyright
- Reddy, B. V. Subba,Kumar, Harish,Reddy, P. Sivaramakrishna,Singarapu, Kiran Kumar
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supporting information
p. 4234 - 4238
(2014/07/21)
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- Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions
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The marine natural product (+)-discodermolide was first isolated in 1990 and, to this day, remains a compelling synthesis target. Not only does the compound possess fascinating biological activity, but it also presents an opportunity to test current methods for chemical synthesis and provides an inspiration for new reaction development. A new synthesis of discodermolide employs a previously undisclosed stereoselective catalytic diene hydroboration and also establishes a strategy for the alkylation of chiral enolates. Furthermore, this synthesis of discodermolide provides the first examples of the asymmetric 1,4-diboration of dienes and borylative diene-aldehyde couplings in complex-molecule synthesis. Borylation-based synthesis: The development of a strategy for stereocontrol in catalytic diene hydroboration enables the synthesis of a critical building block for the assembly of (+)-discodermolide. Combined with asymmetric catalytic diboration, hydroformylation, and borylative aldehyde-diene coupling reactions, (+)-discodermolide could then be prepared from simple hydrocarbon-based building blocks.
- Yu, Zhiyong,Ely, Robert J.,Morken, James P.
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supporting information
p. 9632 - 9636
(2014/10/15)
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- Enantio- and diastereoselective synthesis of highly substituted benzazepines by a multicomponent strategy coupled with organocatalytic and enzymatic procedures
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Enantiomerically pure 4,5-dihydro-1H-benzo[c]azepines with three contiguous stereogenic centers have been assembled by convergent strategy with a good control of diastereoselectivity. The two steps are as follows: an asymmetric organocatalytic Mannich reaction performed on Boc-imines of o-(azidomethyl) benzaldehydes, followed by a one-pot Staudinger/aza-Wittig/Ugi-Joullie sequence. The latter reaction represents one of the first examples of diastereoselective Ugi three-component reaction on a seven-membered cyclic imine. The o-azidomethylbenzaldehydes have been synthesized employing a simple and efficient chemoenzymatic strategy from commercially available building blocks.
- Moni, Lisa,Banfi, Luca,Basso, Andrea,Galatini, Andrea,Spallarossa, Martina,Riva, Renata
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p. 339 - 351
(2014/01/17)
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- Hydrogenation of esters to alcohols with a well-defined iron complex
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We present the first base-free Fe-catalyzed ester reduction applying molecular hydrogen. Without any additives, a variety of carboxylic acid esters and lactones were hydrogenated with high efficiency. Computations reveal an outer-sphere mechanism involving simultaneous hydrogen transfer from the iron center and the ligand. This assumption is supported by NMR experiments.
- Werkmeister, Svenja,Junge, Kathrin,Wendt, Bianca,Alberico, Elisabetta,Jiao, Haijun,Baumann, Wolfgang,Junge, Henrik,Gallou, Fabrice,Beller, Matthias
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supporting information
p. 8722 - 8726
(2014/08/18)
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- Poly(n-butyl-4-vinylpyridinium) borohydride as a new stable and efficient reducing agent in organic synthesis
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Sodium borohydride is stabilized on poly(n-butyl-4-vinylpyridinium) chloride, and it is used as an efficient and regenerable polymer-supported borohydride reagent for the reduction of a variety of carbonyl compounds, such as aldehydes, ketones, α,β-unsaturated carbonyl compounds, α-diketones, and acyloins.
- Khaligh, Nader Ghaffari,Ghasem-Abadi, Parisa Ghods,Mihankhah, Taraneh
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- Electrophilicity and nucleophilicity of commonly used aldehydes
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The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes. A transition state analysis of the KMNO4 promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with experimental results. The validity of the experimental method has been tested using the experimental activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theoretical versus experimental relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chemical reactivity of aldehydes in various reactions. the Partner Organisations 2014.
- Pratihar, Sanjay
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p. 5781 - 5788
(2014/07/22)
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- Unprecedented synthesis of aza-bridged benzodioxepine derivatives through a tandem Rh(ii)-catalyzed 1,3-rearrangement/[3+2] cycloaddition of carbonyltriazoles
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Rh(ii)-catalyzed novel tandem intramolecular cycloisomerizations of aldehydes or ketones with 1-sulfonyl 1,2,3-triazoles have been disclosed, providing a facile protocol to access a series of functionalized aza-bridged benzodioxepine heterocycles.
- Zhang, Yong-Sheng,Tang, Xiang-Ying,Shi, Min
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supporting information
p. 15971 - 15974
(2015/01/08)
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