cas 619-44-3, Methyl 4-iodobenzoate | Articles data

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Flexible bifunctional monoethylphosphonate/carboxylates of Zn(ii) and Co(ii) reinforced with DABCO co-ligand: paradigmatic structural organization withpcutopology
Two novel isostructural phosphonate-monoethylcarboxylate MOFs with the structural formula of [M2(EtBCP)2(DABCO)0.5]·2DMA (M = Zn (2), Co (3); H2EtBCP =O-ethyl-P-(4-carboxyphenyl)phosphonic acid, DABCO = 1,4-diazabicyclo[2.2.2]octane, DMA =N,N-dimethylacetamide) were synthesized and characterized. The frameworks of2and3are sustained by {Zn2(PO2(OEt))2}nmetal-phosphonate- and DABCO-extended {Zn2(COO)4(DABCO)}npaddle-wheel carboxylate chain-SBUs. The chains providing connectivity in three, mutually orthogonal directions are running parallel and are combined in a framework, which could be interpreted as having apcutopology. The simple structure-organization principle, which suggests the possibility of the elongation of the bifunctional ligand with scaling in two directions, allows to view the structures of2and3as prototypes for an isoreticular series. The porosity of both compounds, based on a relatively short ligand, is low: no adsorption of N2was registered, however, CO2is adsorbed readily allowing to estimate the surface area at ～330 m2g?1(～900-1060 m2g?1geometric estimate). The compounds demonstrate a two-step CO2adsorption isotherm both at 195 K (0-1 bar) and 298 K (0-20 bar). The adsorption isotherms are characterized by a gradual (type “F-I”), albeit still relatively steep onset of the second step, associated with structural flexibility/bistability. The estimated pore volumes at the start of the transformation (195 K) for2and3are ～0.11 (0.08P/P0) and 0.12 cm3g?1(0.12P/P0) respectively, which corresponds considerably well to the geometrically calculated accessible volume of ～0.07 cm3g?1for the experimental structure (3.3 ? probe diameter). The structural prerequisites of the observed flexibility of the framework, which might be associated with the non-planarity of the metal-phosphonate moieties, acting as ‘levers’ for propagating mechanical stress, are discussed.
Boldog, Ishtvan,G?kpinar, Serkan,Gil-Hernández, Beatriz,Goldman, Anna,Heering, Christian,Janiak, Christoph,Millan, Simon
p. 2933 - 2944
(2020)
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Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group
While the modular construction of molecules from suitable building blocks is a powerful means to more rapidly generate a diversity of molecules than through customized syntheses, the further evolution of the underlying coupling methodology is key to realize widespread applications. We herein disclose a complementary modular coupling approach to the widely employed Suzuki coupling strategy of boron containing precursors, which relies on organogermane containing building blocks as key orthogonal functionality and an electrophilic (rather than nucleophilic) unmasking event paired with air-stable PdI dimer based bond construction. This allows to significantly shorten the reaction times for the iterative coupling steps and/or to close gaps in the accessible compound space, enabling straightforward access also to iodinated compounds.
Deckers, Kristina,Fricke, Christoph,Hupperich, Daniel,Kreisel, Tatjana,Mendel, Marvin,Queen, Adele E.,Riegger, Julian,Schoenebeck, Franziska
(2022/03/31)

Field-induced single-ion magnets exhibiting tri-axial anisotropy in a 1D Co(ii) coordination polymer with a rigid ligand 4,4′-(buta-1,3-diyne-1,4-diyl)dibenzoate
Herein a 1D Co(ii) coordination polymer of formula [Co(η1-L1)(η2-L1)(py)2(H2O)]n (CoCP) has been synthesised using the rigid H2L1 proligand, containing a long spacer bearing two triple bonds. Single-crystal X-ray diffraction showed that Co(ii) adopts a distorted octahedral geometry. The state-averaged complete active self-consistent field (SA-CASSCF) calculation showed that the ground state of CoCP is a high spin quartet with a highly multiconfigurational character of its electronic structure. Due to the large intra- and intermolecular distances between the spin carriers, the magnetic interactions are negligible and the zero-field splitting (ZFS) effects of cobalt(ii) ions are predominant. This behavior was confirmed by direct current (DC) magnetic measurements and theoretical calculations using the broken-symmetry approach. Quantum chemical calculations indicate that CoCP has a negative axial component possessing mixed tri-axial anisotropy. The DC magnetic susceptibility data were fitted with a Griffith-Figgis Hamiltonian and the obtained parameters are in good agreement with those simulated by the ab initio calculation. Alternating current (AC) magnetic measurements showed a field induced slow magnetic relaxation in CoCP, which is attributed to the hyperfine interaction effects.
C. Silva, Henrique,Ferreira, Glaucio B.,Guedes, Guilherme P.,Matos, Catiúcia R. M. O.,Nunes, Wallace C.,Ronconi, Célia M.,Sarmiento, Charlie V.
p. 15003 - 15014
(2021/11/17)

BODIPY compounds containing 8-(diphenylethynyl)-ester groups as well as synthesis and application thereof
The invention discloses BODIPY compounds containing 8-(diphenylethynyl)-ester groups as well as a preparation method and application thereof. The BODIPY compounds have a structure A. According to theinvention, BODIPY is used as a matrix, a diphenylacetylene rigid structure and an ester-based alkyl chain flexible structure are introduced to the No. 8 site through the Sonogashira coupling reaction,and a series of 8-(diphenylethynyl)-ester-based BODIPY dichroic dyes are designed and synthesized. The maximum emission wavelength of the compounds in dichloromethane is concentrated at about 518 nm,green fluorescence is shown, and good dichroic ratio and ordered parameters are shown in a liquid crystal E7; and the liquid crystal compounds provided by the invention have a liquid crystal mesophase within a temperature range of 50-100 DEG C, can be used for manufacturing liquid crystal display products, and particularly can be used as guest body dyes for guest-host mode liquid crystal displays; and when the compounds are added into the E7 liquid crystal and used in a guest-host display mode, response time can be prolonged, and the effect of quick response is achieved.
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Paragraph 0034-0038

(2021/02/06)

Method for preparing iodo-benzoic acid (ester) by improving moral Michael reaction
The invention discloses a method for preparing iodo-benzoic acid (ester) by improving a moral reaction, and belongs to the technical field of organic synthesis. The method comprises the following steps: preparing and separating the diazonium tetrafluoroborate through diazotization of aminobenzoic acid (ester) and then performing iodination reaction with the iodinated reagent in an organic medium to obtain the corresponding iodo carboxylic acid (ester). The iodo-benzoic acid (ester) prepared by the method has high purity. The method has the advantages of good quality and simple post-treatment, and the product yield reaches 70 - 90%.
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Paragraph 0024; 0037-0038

(2021/11/03)

Mild Copper-Catalyzed Addition of Arylboronic Esters to Di- tert -butyl Dicarbonate: An Easy Access to Methyl Arylcarboxylates
An efficient copper-catalyzed addition of arylboronic esters to (Boc) 2O was developed. The reaction can be conducted under exceedingly mild conditions and is compatible with a variety of synthetically relevant functional groups. It therefore represents a useful alternative route for the synthesis of methyl arylcarboxylates. A preliminary mechanistic study indicated the involvement of an addition-elimination mechanism.
Xu, Jin-Di,Su, Xiao-Bo,Wang, Cai,Yao, Li-Wei,Liu, Jing-Hui,Hu, Guo-Qin
supporting information
p. 833 - 837
(2021/02/26)

Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange
We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.
Boehm, Philip,Cacherat, Bastien,Lee, Yong Ho,Martini, Tristano,Morandi, Bill
supporting information
p. 17211 - 17217
(2021/07/02)

Discovery of [1,2,4]triazole derivatives as new metallo-β-lactamase inhibitors
The emergence and spread of metallo-β-lactamase (MBL)-mediated resistance to β-lactam antibacterials has already threatened the global public health. A clinically useful MBL inhibitor that can reverse β-lactam resistance has not been established yet. We here report a series of [1,2,4]triazole derivatives and analogs, which displayed inhibition to the clinically relevant subclass B1 (Verona integron-encoded MBL-2) VIM-2. 3-(4-Bromophenyl)-6,7-dihydro-5H-[1,2,4]triazolo [3,4-b][1,3]thiazine (5l) manifested the most potent inhibition with an IC50 (half-maximal inhibitory concentration) value of 38.36 μM. Investigations of 5l against other B1 MBLs and the serine β-lactamases (SBLs) revealed the selectivity to VIM-2. Molecular docking analyses suggested that 5l bound to the VIM-2 active site via the triazole involving zinc coordination and made hydrophobic interactions with the residues Phe61 and Tyr67 on the flexible L1 loop. This work provided new triazole-based MBL inhibitors and may aid efforts to develop new types of inhibitors combating MBL-mediated resistance.
Yuan, Chen,Yan, Jie,Song, Chen,Yang, Fan,Li, Chao,Wang, Cheng,Su, Huiling,Chen, Wei,Wang, Lijiao,Wang, Zhouyu,Qian, Shan,Yang, Lingling
(2020/01/11)

Generation of Organozinc Reagents from Arylsulfonium Salts Using a Nickel Catalyst and Zinc Dust
Readily available aryldimethylsulfonium triflates react with zinc powder under nickel catalysis via the selective cleavage of the sp2-hybridized carbon-sulfur bond to produce salt-free arylzinc triflates under mild conditions. This zincation displays superb chemoselectivity and thus represents a protocol that is complementary or orthogonal to existing methods. The generated arylzinc reagents show both high reactivity and chemoselectivity in palladium-catalyzed and copper-mediated cross-coupling reactions.
Yamada, Kodai,Yanagi, Tomoyuki,Yorimitsu, Hideki
p. 9712 - 9718
(2021/01/09)

Methoxylation of Acyl Fluorides with Tris(2,4,6-trimethoxyphenyl)phosphine via C-OMe Bond Cleavage under Metal-Free Conditions
Acyl fluorides are subjected to methoxylation with tris(2,4,6-trimethoxyphenyl)phosphine (TMPP) to afford the corresponding methyl esters in good to excellent yields. This transformation is featured by C(sp2)-OMe bond cleavage under metal-free conditions. Unprecedented utilization of TMPP as a methoxylating agent realized the installation of an OMe group into the desired products.
Ishida, Takumi,Nishihara, Yasushi,Wang, Xiu,Wang, Zhenhua
p. 7526 - 7533
(2020/06/27)

Generation of Organozinc Reagents by Nickel Diazadiene Complex Catalyzed Zinc Insertion into Aryl Sulfonates
The generation of arylzinc reagents (ArZnX) by direct insertion of zinc into the C?X bond of ArX electrophiles has typically been restricted to iodides and bromides. The insertions of zinc dust into the C?O bonds of various aryl sulfonates (tosylates, mesylates, triflates, sulfamates), or into the C?X bonds of other moderate electrophiles (X=Cl, SMe) are catalyzed by a simple NiCl2–1,4-diazadiene catalyst system, in which 1,4-diazadiene (DAD) stands for diacetyl diimines, phenanthroline, bipyridine and related ligands. Catalytic zincation in DMF or NMP solution at room temperature now provides arylzinc sulfonates, which undergo typical catalytic cross-coupling or electrophilic substitution reactions.
Klein, Philippe,Lechner, Vivien Denise,Schimmel, Tanja,Hintermann, Lukas
supporting information
p. 176 - 180
(2019/12/11)

A synthetic 2,3-diarylindole induces microtubule destabilization and G2/M cell cycle arrest in lung cancer cells
The anticancer potential of a synthetic 2,3-diarylindole (PCNT13) has been demonstrated in A549 lung cancer cells by inducing both apoptosis and autophagic cell death. In this report, we designed to connect a fluorophore to the compound via a hydrophilic linker for monitoring intracellular localization. The best position for linker attachment was identified from cytotoxicity and effect on cell morphology of newly synthesized PCNT13 derivatives bearing hydrophilic linker. Cytotoxicity and effect on cell morphology related to the parental compound were used to identify the optimum position for linker attachment in the PCNT13 chemical structure. The fluorophore-PCNT13 conjugate was found to localize in the cytoplasm. Microtubules were found to be one of the cytosolic target proteins of PCNT13, as the compound could inhibit tubulin polymerization in vitro. A molecular docking study revealed that PCNT13 binds at the colchicine binding site on the α/β-tubulin heterodimer. The effect of PCNT13 on microtubule dynamics caused cell cycle arrest in the G2/M phase as analyzed by flow cytometric analysis.
Thanaussavadate, Bongkotrat,Ngiwsara, Lukana,Lirdprapamongkol, Kriengsak,Svasti, Jisnuson,Chuawong, Pitak
supporting information

(2019/11/14)

METHOD FOR THE SYNTHESIS AND PURIFICATION OF ARYL ACID ESTERS
The general inventive concepts are directed to the discovery that certain aryl acids can be esterified under particular conditions to provide the resulting ester as a solid that precipitates in good yield from the reaction mixture. The esters may then be isolated and purified with relative ease. Accordingly, a method for the esterification, isolation, and purification of aryl acids is provided.
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Paragraph 0028

(2019/10/17)

Solvent Adaptive Dynamic Metal-Organic Soft Hybrid for Imaging and Biological Delivery
A solvent responsive dynamic nanoscale metal-organic framework (NMOF) [Zn(1 a)(H2O)2] has been devised based on the self-assembly of ZnII and asymmetric bola-amphiphilic oligo-(p-phenyleneethynylene) (OPE) dicarboxylate linker 1 a having dodecyl and triethyleneglycolmonomethylether (TEG, polar) side chains. In THF solvent, NMOF showed nanovesicular morphology (NMOF-1) with surface decorated dodecyl chains. In water and methanol, NMOF exhibited inverse-nanovesicle (NMOF-2) and nanoscroll (NMOF-3) morphology, respectively, with surface projected TEG chains. The pre-formed NMOFs also unveiled reversible solvent responsive transformation of different morphologies. The flexible NMOF showed cyan emission and no cytotoxicity, allowing live cell imaging. Cisplatin (14.4 wt %) and doxorubicin (4.1 wt %) were encapsulated in NMOF-1 by non-covalent interactions and, in vitro and in vivo drug release was studied. The drug loaded NMOFs exhibited micromolar cytotoxicity.
Samanta, Debabrata,Roy, Syamantak,Sasmal, Ranjan,Saha, Nilanjana Das,Pradeep,Viswanatha, Ranjani,Agasti, Sarit S.,Maji, Tapas Kumar
supporting information
p. 5008 - 5012
(2019/03/11)

Aldehyde effect and ligand discovery in Ru-catalyzed dehydrogenative cross-coupling of alcohols to esters
The presence of different aldehydes is found to have a significant influence on the catalytic performance when using PN(H)P type ligands for dehydrogenation of alcohols. Accordingly, hybrid multi-dentate ligands were discovered based on an oxygen-transfer alkylation of PNP ligands by aldehydes. The relevant Ru-PNN(PO) system provided the desired unsymmetrical esters in good yields via acceptorless dehydrogenation of alcohols. Hydrogen bonding interactions between the phosphine oxide moieties and alcohol substrates likely assisted the observed high chemoselectivity.
Jiang, Xiaolin,Zhang, Jiahui,Zhao, Dongmei,Li, Yuehui
p. 2797 - 2800
(2019/03/27)

Pure white light emission and charge transfer in organogels of symmetrical and unsymmetrical π-chromophoric oligo-: P -(phenyleneethynylene) bola-amphiphiles
Two novel bola-amphiphilic oligo-p-(phenyleneethynylene) (OPE) dicarboxylates have been synthesized having non-polar and mixed-polar side chains. This led to gelation in both with vesicular morphology. Upon in situ loading of a suitable dye and redox-active molecule, pure white light emitting and charge transfer (CT)-gels, respectively, were realized.
Roy, Syamantak,Samanta, Debabrata,Kumar, Pramod,Maji, Tapas Kumar
p. 275 - 278
(2018/01/12)

Efficient synthesis of esters through oxone-catalyzed dehydrogenation of carboxylic acids and alcohols
Since esters are important organic synthesis intermediates, an environmentally friendly oxone catalyzed-esterification of carboxylic acids with alcohols has been developed. A series of carboxylic acid esters are obtained in high yield. This strategy requires mild reaction conditions, providing an attractive alternative for the construction of valuable carbonyl esters. Electron-rich and electron-deficient groups are compatible with the standard conditions and a variety of substrates are demonstrated. Moreover, the reaction could easily be adapted to typical prodrugs, drugs and gram-scale synthesis.
Hou, Fei,Wang, Xi-Cun,Quan, Zheng-Jun
supporting information
p. 9472 - 9476
(2019/01/03)

Microwave assisted synthesis and evaluation of some substituted 1,3,4-oxadiazoles as free radical scavenger
A series of 5-(4-substituted phenyl)-1,3,4-oxadiazoles (4a-h) were prepared from 4-substituted benzoic acid hydrazides (3a-h). Structures of the synthesized compounds were confirmed on the basis of IR, 13C NMR, Mass spectral methods and elemental analysis. The compounds were screened for antioxidant activities using hydrogen peroxide scavenging method comparing with ascorbic acid as standard antioxidant. The results reveal that the compounds possess significant free radical scavenging activities. It is recommended that these compounds might be used in future to generate derivatives for emerging free radical scavenger.
Upadhyay, Prabhat Kumar,Mishra, Pradeep
p. 661 - 666
(2020/07/02)

Solvent-Modulated Emission Properties in a Superhydrophobic Oligo(p-phenyleneethynylene)-Based 3D Porous Supramolecular Framework
A chromophoric oligo(p-phenyleneethynylene) (OPE) bola-amphiphile with dioxyoctyl side chains (H2OPE-C8) has been self-assembled with CdII to form a 1D coordination polymer, {Cd(OPE-C8)(DMF)2(H2O)} (1), which is further interdigitated to form a 2D network. Such 2D networks are further interwoven to form a 3D supramolecular framework with surface-projected alkyl chains. The desolvated framework showed permanent porosity, as realized from the CO2 adsorption profile. 1 showed high water contact angles, portraying its superhydrophobic nature. 1 also showed a linker-based cyan luminescence. Solvent removal led to a bathochromic shift in emission into the green region. Resolvation with N,N-dimethylformamide brought back the original cyan emission, whereas for tetrahydrofuran, ethanol, and methanol, it persisted at an intermediate state. Density functional theory calculations unraveled that, twisting of the OPE phenyl rings generated the red shift in emission.
Roy, Syamantak,Suresh, Venkata M.,Hazra, Arpan,Bandyopadhyay, Arkamita,Laha, Subhajit,Pati, Swapan. K.,Maji, Tapas Kumar
supporting information
p. 8693 - 8696
(2018/08/17)

Metathesis-active ligands enable a catalytic functional group metathesis between aroyl chlorides and aryl iodides
Current methods for functional group interconversion have, for the most part, relied on relatively strong driving forces which often require highly reactive reagents to generate irreversibly a desired product in high yield and selectivity. These approaches generally prevent the use of the same catalytic strategy to perform the reverse reaction. Here we describe a catalytic functional group metathesis approach to interconvert, under CO-free conditions, two synthetically important classes of electrophiles that are often employed in the preparation of pharmaceuticals and agrochemicals—aroyl chlorides (ArCOCl) and aryl iodides (ArI). Our reaction design relies on the implementation of a key reversible ligand C–P bond cleavage event, which enables a non-innocent, metathesis-active phosphine ligand to mediate a rapid aryl group transfer between the two different electrophiles. Beyond enabling a practical and safer approach to the interconversion of ArCOCl and ArI, this type of ligand non-innocence provides a blueprint for the development of a broad range of functional group metathesis reactions employing synthetically relevant aryl electrophiles.
Lee, Yong Ho,Morandi, Bill
p. 1016 - 1022
(2018/09/06)

Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids
A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids has been developed, and the corresponding aryl iodides were obtained in good yields. The method shows some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.
Jiang, Min,Yang, Haijun,Jin, Yunhe,Ou, Lunyu,Fu, Hua
supporting information
p. 1572 - 1577
(2018/06/26)

A 4 - carboxyl preparation process of boric acid (by machine translation)
The invention discloses a 4 - carboxyl boric acid process. In order to to iodine benzoic acid as the raw material, by esterification reaction, sediment reaction and hydrolysis reaction to obtain the target product 4 - carboxyl boric acid, the total yield can reach 88.7%. The process route raw materials are cheap and easy to obtain, after-treatment is convenient, high yield, easy industrialized application. (by machine translation)
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Paragraph 0021; 0022; 0037; 0038; 0045; 0046; 0077; 0078

(2017/08/28)

Revisiting aryl amidine synthesis using metal amide and/or ammonia gas: Novel molecules and their biological evaluation
Amidines, due to their unique biocompatibility and desirable physical characteristics, have been the functionality of choice as a scaffold for large number of drug synthesis. But still synthesis of amidines in the presence of other active functional groups or pharmacophore, remained a challenge. In this work, a simple and reliable protocol for conversion of nitrile-amide to unsubstituted amidine–amide is developed using metal amide and/or ammonia gas. The scope and efficiency of this synthetic strategy are demonstrated on several substrates which differ in functional groups will be discussed. In this process, 10 novel aryl amidines in good yields (upto 85%) were synthesized. Biological evaluation revealed that compound 4-(aminoiminomethyl)-N-(2-furanyl methyl) benzamide (IC50 = 9 μM) and 4-(aminoiminomethyl)-N-(3-pyridinylmethyl) benzamide (73.36% growth inhibition) showed moderate efficacy for cancer cells.
Sahay, Ishani I.,Ghalsasi, Prasanna S.,Singh, Mala,Begum, Rasheedunnisa
p. 1400 - 1408
(2017/07/25)

Design, synthesis and evaluation of antiproliferative activity of melanoma-targeted histone deacetylase inhibitors
The clinical validation of histone deacetylase inhibition as a cancer therapeutic modality has stimulated interest in the development of new generation of potent and tumor selective histone deacetylase inhibitors (HDACi). With the goal of selective delivery of the HDACi to melanoma cells, we incorporated the benzamide, a high affinity melanin-binding template, into the design of HDACi to generate a new series of compounds 10a-b and 11a-b which display high potency towards HDAC1 and HDAC6. However, these compounds have attenuated antiproliferative activities relative to the untargeted HDACi. An alternative strategy furnished compound 14, a prodrug bearing the benzamide template linked via a labile bond to a hydroxamate-based HDACi. This pro-drug compound showed promising antiproliferative activity and warrant further study.
Raji, Idris,Ahluwalia, Kabir,Oyelere, Adegboyega K.
supporting information
p. 744 - 749
(2017/02/18)

Potentiation of the fosmidomycin analogue FR 900098 with substituted 2-oxazolines against Francisella novicida
A library of 33 compounds was screened for potentiation of the antibiotic FR 900098 against the Francisella tularensis surrogate Francisella novicida. From the screen a highly potent 2-oxazoline adjuvant was discovered capable of potentiating FR 900098 with a 1000-fold reduction in MIC against the Francisella sub-species F. novicida and F. philomiragia.
Stephens, Matthew D.,Yodsanit, Nisakorn,Melander, Christian
supporting information
p. 1952 - 1956
(2016/10/22)

SUBSTITUTED BICYCLIC HETEROARYL COMPOUNDS AS RXR AGONISTS
The present invention relates to certain substituted bicyclic compounds that are agonists of RXR and which are therefore useful in the treatment of certain disorders that can be prevented or treated by activation of this receptor. In addition the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders.
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Paragraph 0419

(2016/12/01)

FLUORESCENT SYNTHETIC RETINOIDS
There are described novel compounds of formula I: which R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each as herein defined.
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Page/Page column 41

(2016/05/02)

Palladium-Catalyzed Norbornene-Mediated Tandem Amination/Cyanation Reaction: A Method for the Synthesis of ortho-Aminated Benzonitriles
A palladium-catalyzed, norbornene-mediated tandem amination/cyanation reaction via Catellani-type C-H functionalization was developed using N-benzoyloxyamines as the amination reagent and Zn(CN)2 as the terminating agent. This transformation, in which one C-N bond and one C-C bond are formed, provides an efficient approach for the synthesis of ortho-aminated benzonitriles in one pot from easily accessible starting materials.
Luo, Bo,Gao, Jin-Ming,Lautens, Mark
supporting information
p. 4166 - 4169
(2016/10/12)

Thermolysis of 2-diazo-3-aryl ketoesters: New route to α-aryl malonates and aromatic esters
Thermochemical excitation enabled efficient α-aryl malonates synthesis from 2-diazo-3-aryl ketoesters and alcohols under transition metal-free reaction conditions. Furthermore, an unusual C[sbnd]C bond cleavage and C[sbnd]O/(N) bond formation occurred whe
Zhang, Zhao,Tang, Mengyao,Zang, Lei,Zou, Liang-Hua,Li, Jie
supporting information
p. 5681 - 5684
(2016/11/28)

Using Anilines as Masked Cross-Coupling Partners: Design of a Telescoped Three-Step Flow Diazotization, Iododediazotization, Cross-Coupling Process
The conversion of commercially available anilines into biaryl and biarylacetylene products was realized by using a telescoped, three-reactor flow diazotization/iododediazotization/cross-coupling process. The segmented flow stream created by off-gassing during the Sandmeyer sequence was restored to a continuous column of reaction solution by using a specially designed continuous-flow unit controlled by custom software created in-house. The resultant aryl iodide was then combined with a stream of cross-coupling solution that fed into the final reactor. The system proved versatile as modifications to the diazotization/iododediazotization sequence could be made rapidly to account for any substrate specificity (e.g., solubility problems), leading to a wide substrate scope of Suzuki–Miyaura and Sonogashira cross-coupled products.
Teci, Matthieu,Tilley, Michael,McGuire, Michael A.,Organ, Michael G.
supporting information
p. 17407 - 17415
(2016/11/23)

Rhodium-Catalyzed Double Alkyl-Oxygen Bond Cleavage: An Alkyl Transfer Reaction from Bis/Tris(o-alkyloxyphenyl)phosphine to Aryl Acids
An unprecedented rhodium-catalyzed selective cleavage of double alkyl-oxygen bonds of bis/tris(o-alkyloxyphenyl)phosphine has been realized, in which P atom functions as a directing group and simple aryl acids are the methyl group acceptor to provide methyl esters and a quaternary phosphonium salt. The preliminary mechanism was investigated via an 18O labeling experiment and stoichiometric reaction between a Rh-A crystal and an aromatic acid.
Zhou, Hui,Zhang, Jinlong,Yang, Huameng,Xia, Chungu,Jiang, Gaoxi
supporting information
p. 3406 - 3412
(2016/10/21)

Gold nanoparticle-decorated graphene oxide: Synthesis and application in oxidation reactions under benign conditions
Gold nanoparticles (～13?nm, 4?wt% Au) dispersed on reduced graphene oxide (Au/rGO) surface were prepared via the reduction of gold (III) chloride using sodium citrate on reduced graphene oxide support. The chemical, morphological, and size analyses of Au/rGO by XRD, XPS, TEM, HR-TEM/EDS, AAS, and Raman spectroscopy revealed that the hybrid material comprised of a well-defined rGO support decorated with gold nanoparticles. The ensuing catalyst was evaluated for the oxidation of ethyl benzenes (yields up to 95%) and oxidative esterification of aldehydes (73–97%) using oxygen as an environmentally friendly oxidant in good to excellent yields; reusable and recyclable catalyst displayed high activity without the use of toxic organic solvents.
Pocklanova, Radka,Gawande, Manoj B.,Rathi, Anuj K.,Gawande, Manoj B.,Datta, Kasibhatta Kumara Ramanatha,Ranc, Vaclav,Cepe, Klara,Petr, Martin,Varma, Rajender S.,Kvitek, Libor,Zboril, Radek
p. 121 - 127
(2016/09/07)

Supported cobalt oxide nanoparticles as efficient catalyst in esterification and amidation reactions
Co/SBA-15 nanoparticle catalysts (CoNP) were prepared using a commonly adapted synthetic route and then utilised for esterification and amidation reactions using aromatic and linear chain compounds for the production of long chain esters and amides. The study shows that the use of CoNP catalysts favours the use of aromatic reactants with electron donating substituents specifically in the para position. For the amidation reaction, good to excellent yields were obtained demonstrating tolerance towards differently substituted aromatic compounds. Overall, the synthesized catalysts proved to be efficient and highly versatile, and recyclable under the investigated conditions.
Rajabi, Fatemeh,Raessi, Mojdeh,Arancon, Rick A.D.,Saidi, Mohammad Reza,Luque, Rafael
p. 122 - 126
(2015/01/09)

Rhodium-catalyzed C-H activation of hydrazines leads to isoquinolones with tunable aggregation-induced emission properties
Using an internally oxidizing directing group (DG) strategy, we report a RhIII-catalyzed synthesis of isoquinolones via C-H activation/annulation of benzoylhydrazines and alkynes. Tunable double cascade cyclization of benzoylhydrazines with two equivalents of alkynes led to tetracyclic amides. These N-heterocycles demonstrated adjustable AIE properties.
Yu, Bole,Chen, Ying,Hong, Mei,Duan, Pingping,Gan, Shifeng,Chao, Hui,Zhao, Zujin,Zhao, Jing
supporting information
p. 14365 - 14368
(2015/09/21)

Using the same hydroxamic acid derivative and HDAC8 inhibitor (by machine translation)
Disclosed are: a compound which is capable of inhibiting the function of HDAC8; and an HDAC8 inhibitor. Specifically disclosed is a hydroxamic acid derivative which is characterized by being composed of a compound represented by general formula (1) (wherein X represents an aromatic substituent or an optionally substituted 3-8 membered ring, and n represents an integer of 0-20), or a pharmaceutically acceptable salt, hydrate, solvate or prodrug thereof.
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Paragraph 0029; 0036; 0037

(2016/10/09)

Oxidative esterification of alcohols and aldehydes using supported iron oxide nanoparticle catalysts
The synthesis of esters has become an important industrial methodology over the past years because of the role that they serve in the chemical industry. In this study, we present the use of a novel catalyst for the direct conversion of aldehydes into esters. The yields obtained using supported iron oxide nanoparticle catalysts (FeNP) are very high (>90%). The catalyst is also shown to be very stable as shown by the recyclability study (up to 11 times).
Rajabi, Fatemeh,Arancon, Rick A.D.,Luque, Rafael
p. 101 - 103
(2015/02/19)

Base-free oxidation of alcohols to esters at room temperature and atmospheric conditions using nanoscale Co-based catalysts
The direct oxidation of alcohols to esters with molecular oxygen is an attractive and crucial process for the synthesis of fine chemicals. To date, the heterogeneous catalyst systems that have been identified are based on noble metals or have required the addition of base additives. Here, we show that Co nanoparticles embedded in nitrogen-doped graphite catalyze the aerobic oxidation of alcohols to esters at room temperature under base-free and atmospheric conditions. Our Co@C-N catalytic system features a broad substrate scope for aromatic and aliphatic alcohols as well as diols, giving their corresponding esters in good to excellent yields. This apparently environmentally benign process provides a new strategy with which to achieve selective oxidation of alcohols.
Zhong, Wei,Liu, Hongli,Bai, Cuihua,Liao, Shijun,Li, Yingwei
p. 1850 - 1856
(2015/03/14)

A practical and general ipso iodination of arylboronic acids using N-iodomorpholinium iodide (NIMI) as a novel iodinating agent: mild and regioselective synthesis of aryliodides
A mild and efficient protocol for the ipso-iodination of aryl boronic acids using N-iodomorpholinium iodide (NIMI) generated in situ from morpholine and molecular iodine as a novel iodinating agent has been developed. The addition of a catalytic amount of copper iodide found to promote rate enhancement of the iodination reaction and dramatic increase in the yield depending upon the nature of the boronic acid was observed. The mechanistic study revealed that depending upon the nature of the substrate, either the classical ipso substitution or copper catalysed iododeborylation pathway overall dominates the present iodination reaction. The features such as mild reaction conditions, operational simplicity, high to excellent yields, excellent functional group compatibility and low catalyst loading make this method potentially useful in organic synthesis.
Tale,Toradmal,Gopula
p. 84910 - 84919
(2015/10/28)

An efficient renewable-derived surfactant for aqueous esterification reactions
An efficient and simple approach for the aqueous esterification of a range of carboxylic acids with alcohols has been developed using catalytic amounts of a glucose-derived N-alkanoyl-N-methyl-1-glycamine non-ionic biosurfactant (C12MG). Excellent yields to final products were obtained under mild conditions and the protocol was amenable to both aromatic and long alkyl chain acids (e.g. fatty acids).
Rajabi, Fatemeh,Luque, Rafael
p. 5152 - 5155
(2014/01/23)

On the mechanism of berberine-INF55 (5-Nitro-2-phenylindole) hybrid antibacterials
Berberine-INF55 hybrids are a promising class of antibacterials that combine berberine and the NorA multidrug resistance pump inhibitor INF55 (5-nitro-2-phenylindole) together in one molecule via a chemically stable linkage. Previous studies demonstrated the potential of these compounds for countering efflux-mediated antibacterial drug resistance but they didn't establish whether the compounds function as originally intended, i.e. with the berberine moiety providing antibacterial activity and the attached INF55 component independently blocking multidrug resistance pumps, thereby enhancing the activity of berberine by reducing its efflux. We hypothesised that if the proposed mechanism is correct, then hybrids carrying more potent INF55 pump inhibitor structures should show enhanced antibacterial effects relative to those bearing weaker inhibitors. Two INF55 analogues showing graded reductions in NorA inhibitory activity compared with INF55 were identified and their corresponding berberine-INF55 hybrids carrying equivalent INF55 inhibitor structures synthesised. Multiple assays comparing the antibacterial effects of the hybrids and their corresponding berberine-INF55 analogue combinations showed that the three hybrids all show very similar activities, leading us to conclude that the antibacterial mechanism(s) of berberine-INF55 hybrids is different from berberine-INF55 combinations.
Dolla, Naveen K.,Chen, Chao,Larkins-Ford, Jonah,Rajamuthiah, Rajmohan,Jagadeesan, Sakthimala,Conery, Annie L.,Ausubel, Frederick M.,Mylonakis, Eleftherios,Bremner, John B.,Lewis, Kim,Kelso, Michael J.
p. 1471 - 1480
(2014/12/11)

Copper-catalyzed decarboxylative methylation of aromatic carboxylic acids with PhI(OAc)2
The copper-catalyzed decarboxylative methylation of aromatic carboxylic acids was developed by using PhI(OAc)2 to provide a new strategy for the methylation of aryl acids through the decarboxylation of alkyl acids. The mechanism and the roles of each reactant in the reaction were investigated extensively. Copyright
Jiang, Yuyu,Pan, Shulei,Zhang, Yanghui,Yu, Jingxun,Liu, Hongqiang
supporting information
p. 2027 - 2031
(2014/04/17)

Efficient and simple approaches towards direct oxidative esterification of alcohols
The present article describes novel oxidative protocols for direct esterification of alcohols. The protocols involve successful demonstrations of both "cross" and "self" esterification of a wide variety of alcohols. The cross-esterification proceeds under a simple transition-metal-free condition, containing catalytic amounts of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy)/TBAB (tetra-n-butylammonium bromide) in combination with oxone (potassium peroxo monosulfate) as the oxidant, whereas the self-esterification is achieved through simple induction of Fe(OAc)2/dipic (dipic=2,6-pyridinedicarboxylic acid) as the active catalyst under an identical oxidizing environment. One-pot oxidative esterification: A wide variety of alcohols undergo transition-metal-free (in the presence of oxone/2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)/tetra-n-butylammonium bromide (TBAB)) selective "cross" esterification in moderate to excellent yields (see Figure). The "self" esterification process has however been achieved in the presence of Fe(OAc)2/2,6-pyridinedicarboxylic acid (dipic) as the active catalytic species under a similar oxidizing environment.
Ray, Ritwika,Jana, Rahul Dev,Bhadra, Mayukh,Maiti, Debabrata,Lahiri, Goutam Kumar
supporting information
p. 15618 - 15624
(2016/02/18)

Metal-free iodination of arylboronic acids and the synthesis of biaryl derivatives
A simple, general and efficient method is developed for the metal-free iodination of arylboronic acids. The protocol uses very cheap molecular iodine as the halide source and potassium carbonate as the base. The method is highly tolerant of various functional groups present in the substrates. Importantly, the iodination strategy can also be applied very effectively in the one-pot, two-step synthesis of biaryl derivatives. Georg Thieme Verlag Stuttgart New York.
Niu, Liting,Zhang, Hao,Yang, Haijun,Fu, Hua
supporting information
p. 995 - 1000
(2014/05/06)

5-Nitro-2-furfuriliden derivatives as potential anti-Trypanosoma cruzi agents: Design, synthesis, bioactivity evaluation, cytotoxicity and exploratory data analysis
The anti-Trypanosoma cruzi activity of 5-nitro-2-furfuriliden derivatives as well as the cytotoxicity of these compounds on J774 macrophages cell line and FN1 human fibroblast cells were investigated in this study. The most active compounds of series I and II were 4-butyl-[N′-(5-nitrofuran-2-yl) methylene] benzidrazide (3g; IC50 = 1.05 μM ± 0.07) and 3-acetyl-5-(4-butylphenyl)-2-(5-nitrofuran-2-yl)-2,3-dihydro,1,3,4-oxadiazole (4g; IC50 = 8.27 μM ± 0.42), respectively. Also, compound 3g was more active than the standard drugs, benznidazole (IC50 = 22.69 μM ± 1.96) and nifurtimox (IC50 = 3.78 μM ± 0.10). Regarding the cytotoxicity assay, the 3g compound presented IC 50 value of 28.05 μM (SI = 26.71) against J774 cells. For the FN1 fibroblast assay, 3g showed IC50 value of 98 μM (SI = 93.33). On the other hand, compound 4g presented a cytotoxicity value on J774 cells higher than 400 μM (SI >48), and for the FN1 cells its IC50 value was 186 μM (SI = 22.49). Moreover, an exploratory data analysis, which comprises hierarchical cluster (HCA) and principal component analysis (PCA), was carried out and the findings were complementary. The molecular properties that most influenced the compounds' grouping were C log P and total dipole moment, pointing out the need of a lipophilic/hydrophilic balance in the designing of novel potential anti-T. cruzi molecules.
Palace-Berl, Fanny,Jorge, Salom?o Dória,Pasqualoto, Kerly Fernanda Mesquita,Ferreira, Adilson Kleber,Maria, Durvanei Augusto,Zorzi, Rodrigo Rocha,De Sá Bortolozzo, Leandro,Lindoso, José ?ngelo Lauletta,Tavares, Leoberto Costa
p. 5395 - 5406
(2013/09/02)

Selective oxidation of alcohols to esters using heterogeneous Co 3O4-N@C catalysts under mild conditions
Novel cobalt-based heterogeneous catalysts have been developed for the direct oxidative esterification of alcohols using molecular oxygen as benign oxidant. Pyrolysis of nitrogen-ligated cobalt(II) acetate supported on commercial carbon transforms typical homogeneous complexes to highly active and selective heterogeneous Co3O4-N@C materials. By applying these catalysts in the presence of oxygen, the cross and self-esterification of alcohols to esters proceeds in good to excellent yields.
Jagadeesh, Rajenahally V.,Junge, Henrik,Pohl, Marga-Martina,Radnik, Joerg,Brueckner, Angelika,Beller, Matthias
supporting information
p. 10776 - 10782
(2013/08/23)

Palladium-catalyzed arylation of simple arenes with iodonium salts
The development of an arylation protocol for simple arenes with diaryliodonium salts using the Herrmann-Beller palladacycle catalyst is reported. The reaction takes simple aromatic feedstocks and creates valuable biaryls for use in all sectors of the chem
Storr, Thomas E.,Greaney, Michael F.
supporting information
p. 1410 - 1413
(2013/05/09)

Rapid discovery of highly potent and selective inhibitors of histone deacetylase 8 using click chemistry to generate candidate libraries
To find HDAC8-selective inhibitors, we designed a library of HDAC inhibitor candidates, each containing a zinc-binding group that coordinates with the active-site zinc ion, linked via a triazole moiety to a capping structure that interacts with residues on the rim of the active site. These compounds were synthesized by using click chemistry. Screening identified HDAC8-selective inhibitors including C149 (IC50 = 0.070 μM), which was more potent than PCI-34058 (6) (IC50 = 0.31 μM), a known HDAC8 inhibitor. Molecular modeling suggested that the phenylthiomethyl group of C149 binds to a unique hydrophobic pocket of HDAC8, and the orientation of the phenylthiomethyl and hydroxamate moieties (fixed by the triazole moiety) is important for the potency and selectivity. The inhibitors caused selective acetylation of cohesin in cells and exerted growth-inhibitory effects on T-cell lymphoma and neuroblastoma cells (GI50 = 3-80 μM). These findings suggest that HDAC8-selective inhibitors have potential as anticancer agents.
Suzuki, Takayoshi,Ota, Yosuke,Ri, Masaki,Bando, Masashige,Gotoh, Aogu,Itoh, Yukihiro,Tsumoto, Hiroki,Tatum, Prima R.,Mizukami, Tamio,Nakagawa, Hidehiko,Iida, Shinsuke,Ueda, Ryuzo,Shirahige, Katsuhiko,Miyata, Naoki
p. 9562 - 9575
(2013/01/16)

RXR partial agonist CBt-PMN exerts therapeutic effects on type 2 diabetes without the side effects of RXR full agonists
Treating insulin resistance and type 2 diabetes in rodents, currently known retinoid X receptor (RXR) agonists induce significant adverse effects. Here we introduce a novel RXR partial agonist CBt-PMN (11b), which shows a potent glucose-lowering effect and improvements of insulin secretion and glucose tolerance without the serious adverse effects caused by RXR full agonists. We suggest that RXR partial agonists may be a new class of antitype 2 diabetes drug candidates.
Kakuta, Hiroki,Yakushiji, Nobumasa,Shinozaki, Ryosuke,Ohsawa, Fuminori,Yamada, Shoya,Ohta, Yui,Kawata, Kohei,Nakayama, Mariko,Hagaya, Manabu,Fujiwara, Chisa,Makishima, Makoto,Uno, Shigeyuki,Tai, Akihiro,Maehara, Ami,Nakayama, Masaru,Oohashi, Toshitaka,Yasui, Hiroyuki,Yoshikawa, Yutaka
supporting information; experimental part
p. 427 - 432
(2012/06/30)

Alkylation of substituted benzoic acids in a continuous flow microfluidic microreactor: Kinetics and linear free energy relationships
Alkylation of para-substituted benzoic acids by iodomethane using an organic superbase, 1,8-bis(tetramethylguanidino)naphthalene (TMGN) in DMF was chosen as a model reaction to test the quality of the control of experimental parameters in a continuous flow microfluidic reactor as it is expected to follow a perfect second order kinetics with a large dynamics by varying the substituents. These conditions may be directly used for the synthesis of natural product esters. Because TMGN reacts slowly with iodomethane, the three different mixing strategies between substrate, base and alkylating reagent were compared. The rate constants were determined for the reaction with a set of alkylating agents and in different solvents. In order to test the quality of the obtained data, temperature effect and free energy relationships, which are expected to follow predictable laws, were investigated. The kinetics vary over 6 orders of magnitude and follows a perfect Arrhenius law, allowing the determination of the energies, enthalpies, and entropies of activation. Finally, we established a Hammett linear relationship for a series of 16 substituted benzoic acids, leading to a reaction constant ρ of -0.65 for this reaction. The quality of the obtained kinetics allowed us to discuss the outliers. All kinetics were obtained with less than 0.5 mmol of substrate.
Gholamipour-Shirazi, Azarmidokht,Rolando, Christian
experimental part
p. 811 - 818
(2012/08/07)

Facile aromatic finkelstein iodination (AFI) reaction in 1,3-dimethyl-2-imidazolidinone (DMI)
In this communication, we report the superior role of 1,3-dimethyl-2- imidazolidinone (DMI) as a solvent for aromatic Finkelstein iodination (AFI), the conversion of aryl bromides to aryl iodides. DMI accelerates the reaction rate and affords product(s) that could not be prepared using previous methods. Our findings for AFI avoid the use of toxic solvents such as N,N-dimethylformamide and hexamethylphosphoramide. Taylor & Francis Group, LLC.
Yamashita, Ken-Ichi,Tsuboi, Michihiro,Asano, Motoko S.,Sugiura, Ken-Ichi
experimental part
p. 170 - 175
(2011/11/29)