- Cleavage of immobilized disubstituted triazenes with electrophiles: Solid-phase synthesis of alkyl halides and esters
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An efficient, selective cleavage of polymer-bound disubstituted triazenes with trimethylsilyl halides produces alkyl chlorides, bromides and iodides in good to excellent purities and yields. Similarly, alkyl esters are formed upon cleavage with carboxylic
- Pilot, Claudine,Dahmen, Stefan,Lauterwasser, Frank,Br?se, Stefan
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- Efficient oxidation of alcohols with tert-butyl hydroperoxide catalyzed by Mo(CO)6 supported on multiwall carbon nanotubes
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Efficient oxidation of alcohols with tert-butyl hydroperoxide catalyzed by Mo(CO)6 supported on multiwall carbon nanotubes modified with 4-aminopyridine is reported. The effect of various parameters such as catalyst amount, solvent and oxidant was studied. The catalyst, [Mo(CO) 5@APy-MWCNT], showed high activity not only in the oxidation of benzylic and linear alcohols but also in the oxidation of secondary alcohols. The catalyst can be reused several times without significant loss of its activity.
- Araghi, Mehdi,Ghorbani, Azam,Yeganeh, Faten Eshrati
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- Direct dichlorovinylation of some carbonyl compounds by trichloroethylene under conditions of phase-transfer catalysis
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Reaction of ketones 1 and 3 with trichloroethylene (TRI) carried out in the presence of 50% aq. NaOH and TBAHS as a catalyst, in ethyl ether (phase-transfer catalysis, PTC) afford 1,2-dichlorovinylated ketones 2 and 4, respectively in good yields, usually as mixtures of Z and E isomers. PTC reaction of aldehydes 5 with TRI, carried out with DMSO instead of TBAHS, yields O-dichlorovinylated products 6, as mixtures of isomers in the case of 6a. These products are formed via C- or O-addition of ambident enolate anions to dichloroacetylene (generated from TRI by a base) and fast protonation of highly basic dichlorovinyl anions thus formed. (C) 2000 Elsevier Science Ltd.
- Jończyk, Andrzej,Gierczak, Agnieszka H
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- Metal complexes with atropisomeric sulfur ligands in asymmetric hydroformylation: X-ray structure of [Rh2( μ-biphes) ( cod) 2] (H2biphes = 4,4′-biphenanthrene-3,3′-dithiol)
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The addition of the atropisomeric racemic sulfur compound 4,4′-biphenanthrene-3,3′-dithiol (H2biphes) to a dichloromethane solution of [{M( μ-OMe)(cod)}2] (M = Rh, Ir, cod = cycloocta-1,5 -diene) afforded the dithiolate-bridged compl
- Ruiz, Nuria,Aaliti, Abdellatif,Fornies-Camer, Jorge,Ruiz, Aurora,Claver, Carmen,Cardin, Christine J.,Fabbri, Davide,Gladiali, Serafino
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- Rhodium complexes with a new chiral amino-phosphinite ligand and their behavior as pre-catalysts in the hydroformylation of styrene
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The new amino-phosphinite chiral ligand (Sa)-4-((S)-1-(diphenylphosphinooxy)-3-methylbutan-2-yl)-4,5- dihydro-3H-dinaphtho[2,1-c:1′,2′-e]azepine (1) has been synthesized and the corresponding more stable oxide has been characterized by X-ray an
- Brancatelli,Drommi,Bruno,Faraone
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Read Online
- Tandem catalysis with a bifunctional site-isolated Lewis acid-Bronsted base metal-organic framework, NH2-MIL-101(Al)
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A metal-organic framework (MOF), NH2-MIL-101(Al), which acts as a bifunctional, site-isolated Lewis acid-Bronsted base heterogeneous catalyst, catalyzes a tandem Meinwald rearrangement-Knoevenagel condensation reaction with remarkable substrate selectivity.
- Srirambalaji, Renganathan,Hong, Soonsang,Natarajan, Ramalingam,Yoon, Minyoung,Hota, Raghunandan,Kim, Yonghwi,Ho Ko, Young,Kim, Kimoon
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- Azaphosphine ligand and preparation method and application thereof
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The present invention belongs to the field of homogeneous catalyst ligand technology, specifically a kind of azadronium ligand and preparation method and application thereof. Azazepronium ligand disclosed in the present invention, the structure of which i
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Paragraph 0044; 0045; 0048-0051
(2022/01/20)
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- Synthesis of rac-ɑ-aryl propionaldehydes via branched-selective hydroformylation of terminal arylalkenes using water-soluble Rh-PNP catalyst
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This work detailed the preparation of a class of water-soluble PNP ligands that differed by the nature of the substitute on phenyl ring of ligands. These ligands were incorporated into water-soluble rhodium-PNP complex catalysts that were used to regioselective hydroformylation of a series of terminal arylalkenes, providing efficient access to rac-α-aryl propionaldehydes in good to excellent yield (up to 97%) and branched-regioselectivity (up to 40:1 b/l ratio). Furthermore, gram-scale and diverse synthetic transformation demonstrated synthetic application of this methodology for non-steroidal antiinflammatory drugs.
- Gao, Peng,Ke, Miaolin,Ru, Tong,Liang, Guanfeng,Chen, Fen-Er
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p. 830 - 834
(2021/08/26)
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- Catalytic study of the copper-based magnetic nanocatalyst on the aerobic oxidation of alcohols in water
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A copper-based magnetic nanocatalyst has been prepared by co-precipitation method and characterized by FESEM, EDS, TEM, XRD, XRF, ICP–OES, FTIR, and BET analysis. This new nanocatalyst displays a good activity toward the aerobic oxidation of a wide range of alcohols in water. Moreover, it is recyclable up to five following runs by simple filtration without any significant loss of its catalytic activity.
- Dehkordi, S. Saeid Saei,Albadi, Jalal,Jafari, Abbas Ali,Samimi, Heshmat Allah
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p. 2527 - 2538
(2021/03/24)
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- Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides
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Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C-H and C-C bonds was accessible to the one-pot substitution reaction.
- Ardiansah, Bayu,Kakiuchi, Kiyomi,Morimoto, Tsumoru,Tanimoto, Hiroki,Tomohiro, Takenori
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p. 8738 - 8741
(2021/09/08)
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- Combined Theoretical and Experimental Studies Unravel Multiple Pathways to Convergent Asymmetric Hydrogenation of Enamides
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We present a highly efficient convergent asymmetric hydrogenation of E/Z mixtures of enamides catalyzed by N,P-iridium complexes supported by mechanistic studies. It was found that reduction of the olefinic isomers (E and Z geometries) produces chiral amides with the same absolute configuration (enantioconvergent hydrogenation). This allowed the hydrogenation of a wide range of E/Z mixtures of trisubstituted enamides with excellent enantioselectivity (up to 99% ee). A detailed mechanistic study using deuterium labeling and kinetic experiments revealed two different pathways for the observed enantioconvergence. For α-aryl enamides, fast isomerization of the double bond takes place, and the overall process results in kinetic resolution of the two isomers. For α-alkyl enamides, no double bond isomerization is detected, and competition experiments suggested that substrate chelation is responsible for the enantioconvergent stereochemical outcome. DFT calculations were performed to predict the correct absolute configuration of the products and strengthen the proposed mechanism of the iridium-catalyzed isomerization pathway.
- Yang, Jianping,Massaro, Luca,Krajangsri, Suppachai,Singh, Thishana,Su, Hao,Silvi, Emanuele,Ponra, Sudipta,Eriksson, Lars,Ahlquist, M?rten S. G.,Andersson, Pher G.
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supporting information
p. 21594 - 21603
(2021/12/27)
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- B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of: In situ -formed enamines
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A highly efficient B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of in situ-formed enamines in the presence of water and pinacolborane was developed. Regioselective β-deuteration of tertiary amines was achieved with high chemo- and regioselectivity. D2O was used as a readily available and cheap source of deuterium. Mechanistic studies indicated that B(C6F5)3 could activate water to promote the protonation and reduction of enamines. This journal is
- Wu, Rongpei,Gao, Ke
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supporting information
p. 4032 - 4036
(2021/05/19)
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- Aerobic epoxidation of styrene over Zr-based metal-organic framework encapsulated transition metal substituted phosphomolybdic acid
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Catalytic epoxidation of styrene with molecular oxygen is regarded as an eco-friendly alternative to producing industrially important chemical of styrene oxide (STO). Recent efforts have been focused on developing highly active and stable heterogeneous catalysts with high STO selectivity for the aerobic epoxidation of styrene. Herein, a series of transition metal monosubstituted heteropolyacid compounds (TM-HPAs), such as Fe, Co, Ni or Cu-monosubstituted HPA, were encapsulated in UiO-66 frameworks (denoted as TM-HPA@UiO-66) by direct solvothermal method, and their catalytic properties were investigated for the aerobic epoxidation of styrene with aldehydes as co-reductants. Among them, Co-HPA@UiO-66 showed relatively high catalytic activity, stability and epoxidation selectivity at very mild conditions (313 K, ambient pressure), that can achieve 82 % selectivity to STO under a styrene conversion of 96 % with air as oxidant and pivalaldehyde (PIA) as co-reductant. In addition, the hybrid composite catalyst can also efficiently catalyze the aerobic epoxidation of a variety of styrene derivatives. The monosubstituted Co atoms in Co-HPA@UiO-66 are the main active sites for the aerobic epoxidation of styrene with O2/PIA, which can efficiently converting styrene to the corresponding epoxide through the activation of the in-situ generated acylperoxy radical intermediate.
- Hu, Dianwen,Song, Xiaojing,Zhang, Hao,Chang, Xinyu,Zhao, Chen,Jia, Mingjun
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- Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand
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The hydroformylation of terminal arylalkynes and enynes offers a straightforward synthetic route to the valuable (poly)enals. However, the hydroformylation of terminal alkynes has remained a long-standing challenge. Herein, an efficient and selective Rh-catalyzed hydroformylation of terminal arylalkynes and conjugated enynes has been achieved by using a new stable biphosphoramidite ligand with strong π-acceptor capacity, which affords various important E-(poly)enals in good yields with excellent chemo- and regioselectivity at low temperatures and low syngas pressures.
- Zhao, Jiangui,Zheng, Xueli,Tao, Shaokun,Zhu, Yuxin,Yi, Jiwei,Tang, Songbai,Li, Ruixiang,Chen, Hua,Fu, Haiyan,Yuan, Maolin
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supporting information
p. 6067 - 6072
(2021/08/16)
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- Tandem hydroformylation/hydrogenation over novel immobilized Rh-containing catalysts based on tertiary amine-functionalized hybrid inorganic-organic materials
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Non-phosphorous rhodium-containing catalysts for direct conversion of olefins to alcohols via tandem hydroformylation/hydrogenation have been designed and synthesized. Interaction between Rh(acac)(CO)2 and tertiary amino groups on the surface of mesoporous hybrid organic-inorganic supports yielded materials which were successfully used in the tandem process. Data obtained for a selected catalyst KN demonstrate that rhodium is in the Rh+1 state highly dispersed on the surface and is bonded with nitrogen atoms both before and after use. Evaluation of the catalytic performance shows high activity (hydroformylation TOF 312 h?1), chemoselectivity and stable hydroformylation yield at least in the first 5 cycles with a decrease in alcohol selectivity. The influence of temperature, reaction time, total pressure, and molar CO/H2 ratio of syngas on oxygenate yields is described. Type of the hydroformylation active sites and possible pathways for the observed decrease in hydrogenation are discussed.
- Gorbunov, Dmitry,Karakhanov, Eduard,Maximov, Anton,Naranov, Evgeny,Nenasheva, Maria,Rosenberg, Edward
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- A Low Rhodium Content Smart Catalyst for Hydrogenation and Hydroformylation Reactions
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Abstract: This paper describes the preparation, broad characterization and study of activity in hydrogenation and hydroformylation reactions of an easily produced 0.18% Rh/Al2O3. Analytical studies on fresh and recycled samples shed light on the smart properties of such catalyst. Results showed high activity as well as fine/excellent chemoselectivity or regioselectivity, characteristics that may suggest a wide range of applicability. Graphic Abstract: The low metal content catalyst 0.18% Rh/Al2O3 was very active in both hydrogenation and hydroformylation reactions so providing intermediates for valuable APIs, as Nabumetone and Eletriptan, and a fragrance with a fresh, green-floral smell, that recalls scent of lily of the valley.[Figure not available: see fulltext.]
- Paganelli, Stefano,Tassini, Riccardo,Rathod, Vikas D.,Onida, Barbara,Fiorilli, Sonia,Piccolo, Oreste
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p. 1508 - 1521
(2020/10/15)
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- Chemo- And regioselective hydroformylation of alkenes with CO2/H2over a bifunctional catalyst
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As is well known, CO2 is an attractive renewable C1 resource and H2 is a cheap and clean reductant. Combining CO2 and H2 to prepare building blocks for high-value-added products is an attractive yet challenging topic in green chemistry. A general and selective rhodium-catalyzed hydroformylation of alkenes using CO2/H2 as a syngas surrogate is described here. With this protocol, the desired aldehydes can be obtained in up to 97% yield with 93/7 regioselectivity under mild reaction conditions (25 bar and 80 °C). The key to success is the use of a bifunctional Rh/PTA catalyst (PTA: 1,3,5-triaza-7-phosphaadamantane), which facilitates both CO2 hydrogenation and hydroformylation. Notably, monodentate PTA exhibited better activity and regioselectivity than common bidentate ligands, which might be ascribed to its built-in basic site and tris-chelated mode. Mechanistic studies indicate that the transformation proceeds through cascade steps, involving free HCOOH production through CO2 hydrogenation, fast release of CO, and rhodium-catalyzed conventional hydroformylation. Moreover, the unconventional hydroformylation pathway, in which HCOOAc acts as a direct C1 source, has also been proved to be feasible with superior regioselectivity to that of the CO pathway.
- Hua, Kaimin,Liu, Xiaofang,Wei, Baiyin,Shao, Zilong,Deng, Yuchao,Zhong, Liangshu,Wang, Hui,Sun, Yuhan
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supporting information
p. 8040 - 8046
(2021/11/01)
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- Method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and diphosphine ligand used in method
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The invention discloses a method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and a diphosphine ligand used in the method. According to the invention, indole-substituted phosphoramidite diphosphine ligand which is stable in air and insensitive to light is synthesized by utilizing a continuous one-pot method, and the indole-substituted phosphoramidite diphosphine ligand and a rhodium catalyst are used for jointly catalyzing to successfully achieve a hydroformylation reaction of aromatic terminal alkyne and terminal conjugated eneyne under the condition of synthesis gas for the first time, so that an olefine aldehyde structure compound can be rapidly and massively prepared, and particularly, a polyolefine aldehyde structure compound which is more difficult to synthesize in the prior art can be easily prepared and synthesized, and a novel method is provided for synthesis and modification of drug molecules, intermediates and chemical products.
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Paragraph 0121-0124
(2021/05/29)
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- Tetradentate nitrogen phosphine ligand and preparation method and application thereof
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The invention provides a novel tetradentate nitrogen phosphine ligand as well as a preparation method and an application thereof in an unsaturated olefin hydroformylation reaction. The tetradentate nitrogen phosphine ligand is used for the hydroformylation reaction of olefin, so that the catalyst is more stable in the reaction, is not easy to inactivate at high temperature (more than 200 DEG C), the pressure of synthesis gas required by the reaction is lower, the reaction positive-to-negative ratio is improved, and the selectivity of a main product can be effectively improved.
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Paragraph 0067-0069
(2021/04/07)
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- Methyl-modified cage-type phosphorus ligand and preparation method thereof Preparation method and application thereof
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The invention discloses a methyl-modified cage-type phosphorus ligand, a preparation method and application thereof, in particular to a synthesis design, wherein methyl is further introduced on a phenyl ring of triphenylphosphine, and a methyl-modified cage-type phosphorus ligand is synthesized, and when a methyl meta-substituted cage-type phosphorus ligand is used as a hydroformylation reaction catalyst the proportion of n-structural aldehyde and isomeric aldehyde is 2.6. TOF-1 The methyl-substituted cage-type phosphorus ligand is excellent in performance, stable in property and recyclable, has excellent substrate applicability in the hydroformylation catalytic reaction, has a good industrial application prospect, and has very important significance in metal organic catalysis.
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Paragraph 0075-0084; 0087-0088
(2021/09/15)
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- Insight into decomposition of formic acid to syngas required for Rh-catalyzed hydroformylation of olefins
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Formic acid (FA) is one kind of important bulk chemicals, which is recognized as a sustainable and eco-friendly energy carrier to transport H2 via dehydrogenation or CO via decarbonylation. Expectantly, FA upon decomposition into H2 and CO could be used as the syngas alternative for hydroformylation. In this paper, the behaviors of FA to release H2 as well as CO following the distinct pathways were carefully investigated for the first time, and then established a new hydroformylation protocol free of syngas. It was found that the atmospheric hydroformylation of olefins with formic acid (FA) as syngas alternative was smoothly fulfilled over Xantphos (L1) modified Rh-catalyst under mild conditions (80 °C, Rh concentration 1 mol %, 14 h), resulting in >90% conversion of the olefins along with the high selectivity to the target aldehydes (>93%). By using FA as syngas source, the side-reaction of olefin-hydrogenation was greatly depressed. The in situ FT-IR and the high-pressure 1H NMR spectroscopic analyses were applied to reveal how FA behaves dually as CO surrogate and hydrogen source over L1-Rh(acac)(CO)2 catalytic system, based on which the deeply insight into the catalytic mechanism of hydroformylation of olefins with FA as syngas alternative was offered.
- Liu, Lei,Chen, Xiao-Chao,Yang, Shu-Qing,Yao, Yin-Qing,Lu, Yong,Liu, Ye
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p. 406 - 415
(2020/12/07)
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- Selective Production of Linear Aldehydes and Alcohols from Alkenes using Formic Acid as Syngas Surrogate
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Performing carbonylation without the use of carbon monoxide for high-value-added products is an attractive yet challenging topic in sustainable chemistry. Herein, effective methods for producing linear aldehydes or alcohols selectively with formic acid as both carbon monoxide and hydrogen source have been described. Linear-selective hydroformylation of alkenes proceeds smoothly with up to 88 % yield and >30 regioselectivity in the presence of single Rh catalyst. Strikingly, introducing Ru into the system, the dual Rh/Ru catalysts accomplish efficient and regioselective hydroxymethylation in one pot. The present processes utilizing formic acid as syngas surrogate operate simply under mild condition, which opens a sustainable way for production of linear aldehydes and alcohols without the need for gas cylinders and autoclaves. As formic acid can be readily produced via CO2 hydrogenation, the protocols represent indirect approaches for chemical valorization of CO2.
- Chen, Junjun,Hua, Kaimin,Liu, Xiaofang,Deng, Yuchao,Wei, Baiyin,Wang, Hui,Sun, Yuhan
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p. 9919 - 9924
(2021/05/31)
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- Copper-catalyzed hydroformylation and hydroxymethylation of styrenes
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Hydroformylation catalyzed by transition metals is one of the most important homogeneously catalyzed reactions in industrial organic chemistry. Millions of tons of aldehydes and related chemicals are produced by this transformation annually. However, most of the applied procedures use rhodium catalysts. In the procedure described here, a copper-catalyzed hydroformylation of alkenes has been realized. Remarkably, by using a different copper precursor, the aldehydes obtained can be further hydrogenated to give the corresponding alcohols under the same conditions, formally named as hydroxymethylation of alkenes. Under pressure of syngas, various aldehydes and alcohols can be produced from alkenes with copper as the only catalyst, in excellent regioselectivity. Additionally, an all-carbon quaternary center containing ethers and formates can be synthesized as well with the addition of unactivated alkyl halides. A possible reaction pathway is proposed based on our results. This journal is
- Franke, Robert,Geng, Hui-Qing,Meyer, Tim,Wu, Xiao-Feng
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p. 14937 - 14943
(2021/12/02)
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- Oxidation of alcohols using an oxoammonium salt bearing the nitrate anion
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A methodology for the oxidation of alcohols to the corresponding carbonyl compounds is reported using a sub-stoichiometric quantity of an oxoammonium salt bearing the nitrate counterion. The approach proves successful for the oxidation of a range of alcohol substrates including those bearing an oxygen atom β to the site of oxidation or an α-trifluoromethyl moiety. The mechanism of the reaction has been probed and also gives an insight into the previously reported nitric acid mediated oxidation of alcohols.
- Miller, Shelli A.,Sandoval, Arturo León,Leadbeater, Nicholas E.
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supporting information
(2019/12/25)
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- FMPhos: Expanding the catalytic capacity of small-bite-angle bisphosphine ligands in regioselective alkene hydrofunctionalizations
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In contrast to the plethora of large-bite-angle bisphosphine ligands available to transition-metal catalysis, the development of small-bite-angle bisphosphine ligands has suffered from the limited structural variations accessible on their single-atom-containing backbones. Herein, we report the design and applications of a discrete very small bite-angle bisphosphine ligand, namely, FMPhos. Featuring a fluorene?methylene unit appended on the single-carbon linker, the ligand harbors an unusually rigid backbone that presumably stabilizes its complexation with transition metals during catalysis. Compared with the known dppm ligand, it exhibited superior reactivity and regioselectivity in a number of alkene hydrofunctionalization reactions, catalyzed by iridium and rhodium.
- Chen, Xiao-Yang,Zhou, Xukai,Wang, Jianchun,Dong, Guangbin
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p. 14349 - 14358
(2020/12/21)
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- Fast Hydrocarbon Oxidation by a High-Valent Nickel–Fluoride Complex
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In the search for highly reactive oxidants we have identified high-valent metal–fluorides as a potential potent oxidant. The high-valent Ni–F complex [NiIII(F)(L)] (2, L=N,N′-(2,6-dimethylphenyl)-2,6-pyridinedicarboxamidate) was prepared from [NiII(F)(L)]? (1) by oxidation with selectfluor. Complexes 1 and 2 were characterized by using 1H/19F NMR, UV-vis, and EPR spectroscopies, mass spectrometry, and X-ray crystallography. Complex 2 was found to be a highly reactive oxidant in the oxidation of hydrocarbons. Kinetic data and products analysis demonstrate a hydrogen atom transfer mechanism of oxidation. The rate constant determined for the oxidation of 9,10-dihydroanthracene (k2=29 m?1 s?1) compared favorably with the most reactive high-valent metallo-oxidants. Complex 2 displayed reaction rates 2000–4500-fold enhanced with respect to [NiIII(Cl)(L)] and also displayed high kinetic isotope effect values. Oxidative hydrocarbon and phosphine fluorination was achieved. Our results provide an interesting direction in designing catalysts for hydrocarbon oxidation and fluorination.
- Lovisari, Marta,McDonald, Aidan R.,Mondal, Prasenjit,Twamley, Brendan
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supporting information
p. 13044 - 13050
(2020/06/05)
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- Magnetically recoverable porphyrin-based nanocatalysts for the effective oxidation of olefins with hydrogen peroxide: A comparative study
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In this paper, preparation, characterization and catalytic applications of metalloporphyrin-based magnetic nanocatalysts were investigated. meso-Tetrakis(4-carboxyphenyl)porphyrinatoiron(iii) chloride (Fe(TCPP)Cl) and meso-tetrakis(4-carboxyphenyl)porphyrinatomanganese(iii) acetate (Mn(TCPP)OAc) were separately immobilized onto the surface of amine functionalized magnetic nanoparticles (Fe3O4/SiO2/NH2) via covalent attachment. The obtained nanocatalysts were characterized using FT-IR and UV-Vis and atomic absorption spectroscopy, X-ray powder diffraction (XRD), vibrating sample magnetometry (VSM), thermogravimetric analysis (TGA), and transmission electron microscopy (TEM). The catalytic efficiency of Fe3O4/SiO2/NH2-Fe(TCPP)Cl and Fe3O4/SiO2/NH2-Mn(TCPP)OAc for the green oxidation of alkenes with H2O2 was investigated in a comparative manner. The Mn-porphyrin based magnetic nanocatalyst shows higher catalytic efficiency compared to the Fe-porphyrin. In addition, the prepared magnetic nanocatalyst exhibited excellent reusability and could be reused at least five times without significant leaching or loss of activity. This journal is
- Rayati, Saeed,Moradi, Dana,Nejabat, Fatemeh
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p. 19385 - 19392
(2020/11/23)
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- Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation
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A magnesium-catalyzed regiodivergent C-O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mechanistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain the different mechanisms of the C-O bond activation and product formation.
- Magre, Marc,Paffenholz, Eva,Maity, Bholanath,Cavallo, Luigi,Rueping, Magnus
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supporting information
p. 14286 - 14294
(2020/09/15)
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- Prospects of Heterogeneous Hydroformylation with Supported Single Atom Catalysts
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The potential of oxide-supported rhodium single atom catalysts (SACs) for heterogeneous hydroformylation was investigated both theoretically and experimentally. Using high-level domain-based local-pair natural orbital coupled cluster singles doubles with
- Amsler, Jonas,Sarma, Bidyut B.,Agostini, Giovanni,Prieto, Gonzalo,Plessow, Philipp N.,Studt, Felix
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p. 5087 - 5096
(2020/03/16)
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- Styrene Hydroformylation with In Situ Hydrogen: Regioselectivity Control by Coupling with the Low-Temperature Water–Gas Shift Reaction
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The hydroformylation of olefins is one of the most important homogeneously catalyzed industrial reactions for aldehyde synthesis. Various ligands can be used to obtain the desired linear aldehydes in the hydroformylation of aliphatic olefins. However, in the hydroformylation of aromatic substrates, branched aldehydes are formed preferentially with common ligands. In this study, a novel approach to selectively obtain linear aldehydes in the hydroformylation of styrene and its derivatives was developed by coupling with a water–gas shift reaction on a Rh single-atom catalyst without the use of ligands. Detailed studies revealed that the hydrogen generated in situ from the water–gas shift is critical for the highly regioselective formation of linear products. The coupling of a traditional homogeneous catalytic process with a heterogeneous catalytic reaction to tune product selectivity may provide a new avenue for the heterogenization of homogenous catalytic processes.
- Chen, Fang,Lang, Rui,Li, Tianbo,Qiao, Botao,Su, Yang,Wang, Aiqin,Wang, Hua,Zhang, Tao
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supporting information
p. 7430 - 7434
(2020/03/13)
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- Visible-light mediated facile dithiane deprotection under metal free conditions
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Visible light mediated facile and selective dithiane deprotection under metal free conditions is developed. Eosin Y (1 mol%) proved to be an effective catalyst for the dithiane deprotection under the ambient photoredox conditions. The standard household compact fluorescent light source (CFL bulb) proved to be effective under open-air conditions in aqueous acetonitrile at room temperature. The protocol that exhibits a broad substrate scope and functional group tolerance has been shown to expand to a range of transformations for the electron-rich and -deficient thioacetals and thioketals. The synthetic utility of this protocol has also been demonstrated by gram-scale application.
- Dharpure, Pankaj D.,Bhowmick, Anindita,Warghude, Prakash K.,Bhat, Ramakrishna G.
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- Two-way homologation of aliphatic aldehydes: Both one-carbon shortening and lengthening via the same intermediate
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Aliphatic aldehydes can be homologated to both one-carbon shorter and one-carbon longer homologous carbonyl compounds through the 2–4 steps of reactions via the same intermediates, β,γ-unsaturated α-nitrosulfones, prepared from the proline-catalyzed sequential reactions of several aliphatic aldehydes with phenylsulfonylnitromethane. While the oxidative cleavage of the key intermediates gave one-carbon less homologous carbonyl compounds, the reduction of the same key intermediates followed by an oxidation produced one-carbon more homologous carbonyl compounds.
- Yoo, Jae Won,Seo, Youngran,Park, Jong Beom,Kim, Young Gyu
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- HFIP-promoted synthesis of substituted tetrahydrofurans by reaction of epoxides with electron-rich alkenes
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In the present work, the employment of fluorinated alcohols, specifically 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), as solvent and promoter of the catalyst-free synthesis of substituted tetrahydrofuranes through the addition of electron-rich alkenes to epoxydes is described. The unique properties of this fluorinated alcohol, which is very different from their non-fluorinated analogs, allows carrying out this new straightforward protocol under smooth reaction conditions affording the corresponding adducts in moderate yields in the majority of cases. Remarkably, this methodology has allowed the synthesis of new tetrahydrofuran-based spiro compounds as well as tetrahydrofurobenzofuran derivatives. The scope and limitations of the process are also discussed. Mechanistic studies were also performed pointing towards a purely ionic or a SN2-type process depending on the nucleophilicity of the alkene employed.
- Baeza, Alejandro,Llopis, Natalia
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- 3-BocNH-ABNO-catalyzed aerobic oxidation of alcohol at room temperature and atmospheric pressure
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A transition-metal-free catalytic system has been developed for selective transformation of alcohol to aldehydes or ketones. The reactions were performed with 3-(tert-butoxycarbonylamino)-9-azabicyclo[3.3.1]nonane N-oxyl (3-BocNH-ABNO) as the catalyst, NaNO2 as the co-catalyst, molecular oxygen as the terminal oxidant, and AcOH as the solvent under room temperature. This catalytic system exhibited broad functional group tolerance. A series of alcohol substrates, including primary and secondary benzylic alcohols, heteroaromatic analogues, primary and secondary aliphatic alcohols, could be converted into their corresponding aldehydes and ketones in good conversions and selectivities.
- Zhao, Yajing,Li, Yutong,Shen, Zhenlu,Hu, Xinquan,Hu, Baoxiang,Jin,Sun, Nan,Li, Meichao
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supporting information
(2019/08/06)
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- Preparation method of 2-phenylpropionic acid
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The invention discloses a preparation method of 2-phenylpropionic acid. The preparation method of the 2-phenylpropionic acid comprises the following steps: (1) preparing 2-phenylpropyl aldehyde: dissolving styrene into methanol, adding catalysts acetone dicarbonyl rhodium and triethylamine, performing reaction and collecting fraction to obtain the 2-phenylpropyl aldehyde; and (2) preparing 2-phenylpropionic acid: dissolving the 2-phenylpropyl aldehyde into acetonitrile, adding an aqueous solution of hydrogen peroxide and sodium dihydrogen phosphate, adding a sodium hypochlorite solution into the system dropwise, performing reaction after adding dropwise, adding anhydrous sodium sulfite, standing and layering, taking an organic phase, washing with water, distilling, performing reduced-pressure distillation and collecting fraction to obtain the 2-phenylpropionic acid. During synthesis of the 2-phenylpropionic acid, the reaction can be completed only by two steps, so that the reaction steps are reduced, the reaction yield is increased, the cost is reduced, the yield can reach to 80 percent or more, the conversion rate is high, and the prepared product has stable quality and high purity.
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Paragraph 0017; 0019-0022
(2019/02/04)
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- MICROCAPSULES AND PROCESSES FOR THEIR PREPARATION
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The present invention provides microcapsules encapsulating hydrophilic or hydrophobic active agents in an inorganic shell, processes for their preparation and compositions comprising them.
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Page/Page column 28-30
(2019/06/11)
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- Retro-Corey-Chaykovsky Epoxidation: Converting Geminal Disubstituted Epoxides to Ketones
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Corey-Chaykovsky epoxidation has been widely applied in the conversion of aldehydes and ketones to epoxides with sulfonium and sulfoxonium ylides. The reverse transformation is realized for conversion of geminal disubstituted epoxides to ketones in the presence of DABCO in refluxing mesitylene. The method is a weak basic transformation from epoxides to ketones with loss of a methylene group and can be applied as an alternative strategy of the acid-catalyzed Meinwald rearrangement or oxidation for conversion of epoxides to carbonyl compounds.
- Li, Siqi,Li, Pingfan,Xu, Jiaxi
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- Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines
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The isomerization of epoxides to aldehydes using the readily available Crabtree's reagent is described. The aldehydes were transformed into synthetically useful amines by a one-pot reductive amination using pyrrolidine as imine-formation catalyst. The reactions worked with low catalyst loadings in very mild conditions. The procedure is operationally simple and tolerates a wide range of functional groups. A DFT study of its mechanism is presented showing that the isomerization takes place via an iridium hydride mechanism with a low energy barrier, in agreement with the mild reaction conditions. (Figure presented.).
- Cabré, Albert,Cabezas-Giménez, Juanjo,Sciortino, Giuseppe,Ujaque, Gregori,Verdaguer, Xavier,Lledós, Agustí,Riera, Antoni
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p. 3624 - 3631
(2019/07/10)
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- Microwave-assisted synthesis of α-aminophosphine oxides
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Aminophosphine oxides and bis(phosphinoylmethyl)amines were synthesized by the microwave (MW)-assisted Kabachnik-Fields reaction of primary amines, paraformaldehyde and secondary phosphine oxides. The bisphosphines obtained after deoxygenation of the bis(phosphinoymethyl)amine derivatives were utilized in the synthesis of cyclic transition metal complexes.
- Tripolszky, Anna,Bálint, Erika,Keglevich, Gy?rgy
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p. 345 - 348
(2019/03/07)
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- Highly Enantioselective Catalytic Kinetic Resolution of α-Branched Aldehydes through Formal Cycloaddition with Homophthalic Anhydrides
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A new catalytic methodology was developed to promote an efficient one-pot kinetic resolution of racemic aldehydes with selectivity (s*) of up to 91 (99:1 d.r., >99 % ee) in a cycloaddition reaction with enolizable anhydrides to afford dihydroisocoumarin products (a core prevalent in natural products and molecules of medicinal interest) containing three contiguous stereocentres.
- Farid, Umar,Aiello, Maria Luisa,Connon, Stephen J.
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p. 10074 - 10079
(2019/07/18)
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- Mechanism of the Bis(imino)pyridine-Iron-Catalyzed Hydromagnesiation of Styrene Derivatives
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Iron-catalyzed hydromagnesiation of styrene derivatives offers a rapid and efficient method to generate benzylic Grignard reagents, which can be applied in a range of transformations to provide products of formal hydrofunctionalization. While iron-catalyzed methodologies exist for the hydromagnesiation of terminal alkenes, internal alkynes, and styrene derivatives, the underlying mechanisms of catalysis remain largely undefined. To address this issue and determine the divergent reactivity from established cross-coupling and hydrofunctionalization reactions, a detailed study of the bis(imino)pyridine iron-catalyzed hydromagnesiation of styrene derivatives is reported. Using a combination of kinetic analysis, deuterium labeling, and reactivity studies as well as in situ 57Fe M?ssbauer spectroscopy, key mechanistic features and species were established. A formally iron(0) ate complex [iPrBIPFe(Et)(CH2a?CH2)]- was identified as the principle resting state of the catalyst. Dissociation of ethene forms the catalytically active species which can reversibly coordinate the styrene derivative and mediate a direct and reversible β-hydride transfer, negating the necessity of a discrete iron hydride intermediate. Finally, displacement of the tridentate bis(imino)pyridine ligand over the course of the reaction results in the formation of a tris-styrene-coordinated iron(0) complex, which is also a competent catalyst for hydromagnesiation.
- Neate, Peter G. N.,Greenhalgh, Mark D.,Brennessel, William W.,Thomas, Stephen P.,Neidig, Michael L.
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supporting information
p. 10099 - 10108
(2019/07/04)
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- Peroxygenase-Catalysed Epoxidation of Styrene Derivatives in Neat Reaction Media
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Biocatalytic oxyfunctionalisation reactions are traditionally conducted in aqueous media limiting their production yield. Here we report the application of a peroxygenase in neat reaction conditions reaching product concentrations of up to 360 mM.
- Alcalde, Miguel,Arends, Isabel W. C. E.,Hollmann, Frank,Paul, Caroline E.,Rauch, Marine C. R.,Tieves, Florian
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- Efficient water-soluble catalytic system RhI-CAP for biphasic hydroformylation of olefins
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Rhodium-catalysed hydroformylation of styrene and aliphatic olefins under biphasic conditions in the presence of watersoluble 1,4,7-triaza-9-phosphatricyclo[5.3.2.14,9]tridecane (CAP) chemoselectively affords aldehydes. Multiple catalyst reuse without loss in performance is demonstrated.
- Eliseev, Oleg L.,Bondarenko, Tatyana N.,Britvin, Sergey N.,Khodorchenko, Polina P.,Lapidus, Albert L.
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p. 264 - 266
(2018/06/01)
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- Tandem hydroformylation/aldol condensation reactions: Synthesis of unsaturated ketones from olefins
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Platinum-catalysed tandem hydroformylation/aldol condensation reaction of vinyl aromatics and ketones toward the corresponding α,β-unsaturated ketones were performed under syngas atmosphere in the presence of acid co-catalysts. The in situ generated catal
- Kollár, László,Pongrácz, Péter
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p. 184 - 188
(2018/05/07)
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- Microwave-assisted isomerizations of epoxides to allylic alcohols
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The present work reports a study on the isomerization reactions of several alkyl epoxides to the corresponding allylic alcohols or bicyclic alcohols under microwave irradiation. The reaction occurred in the presence of lithium diisopropylamide as a base and different experimental conditions in terms of solvent, amount of the base, times and temperatures. The traditional heating with an oil-bath and the use of alternative organometallic bases, as the Lochmann-Schlosser bases, have been furthermore compared with the microwave heating. The results obtained show that the use of microwave irradiations on promoting the isomerization of epoxides gives access to a series of synthetically useful products, among which allylic alcohols and bicyclic alcohols, depending on the starting substrate.
- Consiglio, Gabriella Barozzino,Mordini, Alessandro
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p. 447 - 454
(2018/05/22)
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- Copper-catalyzed vinylogous aerobic oxidation of unsaturated compounds with air
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A mild and operationally simple copper-catalyzed vinylogous aerobic oxidation of β,γ- and α,β-unsaturated esters is described. This method features good yields, broad substrate scope, excellent chemo- and regioselectivity, and good functional group tolerance. This method is additionally capable of oxidizing β,γ- and α,β-unsaturated aldehydes, ketones, amides, nitriles, and sulfones. Furthermore, the present catalytic system is suitable for bisvinylogous and trisvinylogous oxidation. Tetramethylguanidine (TMG) was found to be crucial in its role as a base, but we also speculate that it serves as a ligand to copper(II) triflate to produce the active copper(II) catalyst. Mechanistic experiments conducted suggest a plausible reaction pathway via an allylcopper(II) species. Finally, the breadth of scope and power of this methodology are demonstrated through its application to complex natural product substrates.
- Zhang, Hai-Jun,Schuppe, Alexander W.,Pan, Shi-Tao,Chen, Jin-Xiang,Wang, Bo-Ran,Newhouse, Timothy R.,Yin, Liang
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p. 5300 - 5310
(2018/04/24)
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- Selective ligand-free cobalt-catalysed reduction of esters to aldehydes or alcohols
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Cobalt(ii) salts combined with NaBHEt3 and eventually a base catalyse efficiently and selectively the reduction of esters to aldehydes or alcohols through hydrosilylation by using phenylsilane. Catalyst characterisation by XRD, XPS, TEM and STEM analyses indicates the materials were partially crystalline with the presence of cobalt nanoparticles. Control experiments suggested low valent Co(0) was the active catalytic species involved.
- Rysak, Vincent,Descamps-Mandine, Armel,Simon, Pardis,Blanchard, Florent,Burylo, Laurence,Trentesaux, Martine,Vandewalle, Maxence,Collière, Vincent,Agbossou-Niedercorn, Francine,Michon, Christophe
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p. 3504 - 3512
(2018/07/29)
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- Asymmetric α-Allylation of Aldehydes with Alkynes by Integrating Chiral Hydridopalladium and Enamine Catalysis
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A palladium-catalyzed asymmetric α-allylation of aldehydes with alkynes has been established by integrating the catalysis of enamine and chiral hydridopalladium complex that is reversibly formed from the oxidative addition of Pd(0) to chiral phosphoric acid. The ternary catalyst system, consisting of an achiral palladium complex, a primary amine, and a chiral phosphoric acid allows the reaction to tolerate a wide scope of α,α-disubstituted aldehydes and alkynes, affording the corresponding allylation products in high yields and with excellent levels of enantioselectivity.
- Su, Yong-Liang,Li, Lu-Lu,Zhou, Xiao-Le,Dai, Zhen-Yao,Wang, Pu-Sheng,Gong, Liu-Zhu
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p. 2403 - 2406
(2018/04/27)
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- A TEMPO-like nitroxide combined with an alkyl-substituted pyridine: An efficient catalytic system for the selective oxidation of alcohols with iodine
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An efficient method for the oxidation of alcohols to aldehydes or ketones in a two-phase CH2Cl2/NaHCO3 (aq.) system, using iodine and catalytic amounts of 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxyl and 2,4,6-trimethylpyridine, was developed. The performance of the method was demonstrated by the selective oxidation of 37 variously substituted alcohols in ≥90% yield, including the gram-scale synthesis of the important chemical 2,5-diformylfuran from biomass-derived 5-hydroxylmethylfurfural.
- Kashparova, Vera P.,Klushin, Victor A.,Zhukova, Irina Yu.,Kashparov, Igor S.,Chernysheva, Daria V.,Il'chibaeva, Irina B.,Smirnova, Nina V.,Kagan, Efim Sh.,Chernyshev, Victor M.
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supporting information
p. 3517 - 3521
(2017/10/05)
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- TEMPO-Mediated Oxidative Deformylation of Aldehydes: Applications in the Synthesis of Polyketide Fragments
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A TEMPO-mediated oxidative deformylation of aldehydes is reported that yields the TEMPO adducts, which can be further oxidized to the corresponding ketones. The focus of this work was on the optimization of a synthetic protocol for use in natural product
- Kipke, Andreas,Sch?ning, Kai-Uwe,Yusubov, Mekhman,Kirschning, Andreas
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p. 6906 - 6913
(2017/12/26)
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- Calix[4]arene-fused phospholes
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An upper rim, o-(diphenylphosphinyl)phenyl-substituted calix[4]arene has been prepared and its coordinative properties investigated. When heated in the presence of palladium, the new biarylphosphine undergoes conversion into two diastereomeric, calixarene-fused phospholes. In both, the P lone pair adopts a fixed orientation with respect to the calixarene core. The more hindered phosphole (8), i.e. the one with the endo-oriented lone pair (cone angle 150°-175°), forms complexes having their metal centre positioned very near the calixarene unit but outside the cavity, thus inducing an unusual chemical shift of one of the methylenic ArCH2Ar protons owing to interactions with the metal centre. As expected for dibenzophospholes, the complex [Rh(acac)(CO)·8], when combined with one equivalent of free 8, efficiently catalyses the hydroformylation of styrene, the catalytic system displaying high regioselectivity in favour of the branched aldehyde (b/l ratio up to 30). The optical and redox properties of the derivatives have also been investigated.
- Elaieb, Fethi,Sémeril, David,Matt, Dominique,Pfeffer, Michel,Bouit, Pierre-Antoine,Hissler, Muriel,Gourlaouen, Christophe,Harrowfield, Jack
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p. 9833 - 9845
(2017/08/10)
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- Backbone-Modified Bisdiazaphospholanes for Regioselective Rhodium-Catalyzed Hydroformylation of Alkenes
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A series of tetraaryl bisdiazaphospholane (BDP) ligands were prepared varying the phosphine bridge, backbone, and substituents in the 2- and 5-positions of the diazaphospholane ring. The parent acylhydrazine backbone was transformed to an alkylhydrazine via a borane reduction procedure. These reduced ligands contained an all sp3 hybridized ring mimicking the all sp3 phospholane of (R,R)-Ph-BPE, a highly selective ligand in asymmetric hydroformylation. The reduced bisdiazaphospholane (red-BDP) ligands were shown crystallographically to have an increased C-N-N-C torsion angle - this puckering resembles the structure of (R,R)-Ph-BPE and has a dramatic influence on regioselectivity in rhodium catalyzed hydroformylation. The red-BDPs demonstrated up to a 5-fold increase in selectivity for the branched aldehyde compared to the acylhydrazine parent ligands. This work demonstrates a facile procedure for increased branched selectivity from the highly active and accessible class of BDP ligands in hydroformylation.
- Wildt, Julia,Brezny, Anna C.,Landis, Clark R.
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p. 3142 - 3151
(2017/09/05)
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- Rhenium complex-catalyzed Meinwald rearrangement reactions of oxiranes
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The Meinwald rearrangement reaction of oxiranes to the corresponding carbonyl compounds is efficiently catalyzed by the ReBr(CO)5 complex.
- Umeda, Rui,Muraki, Masahito,Nakamura, Yuudai,Tanaka, Tomoyuki,Kamiguchi, Kyohei,Nishiyama, Yutaka
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p. 2393 - 2395
(2017/05/29)
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- "release and catch" catalysis by tungstate species for the oxidative cleavage of olefins
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The oxidative cleavage of olefins produces valuable carbonyl compounds, and thus, the development of green catalytic methods using H2O2 as an oxidant is highly desired. In this work, we have successfully developed an efficient catalytic system for the oxidative cleavage of olefins and related compounds using H2O2. In the presence of tungstate species supported on zinc-modified tin dioxide (W/Zn-SnO2), the oxidative cleavage of 1-methyl-1-cyclohexene proceeds efficiently through multistep reaction pathways involving oxygenation, hydrolysis, perhydrolysis, and isomerization reactions. In this reaction system, active peroxotungstate species, generated by the reaction of the supported tungstate species with H2O2, are released into the solution during the course of the reaction. At the end of the reaction (after the complete consumption of H2O2), the released tungstate species are re-captured by the support. The W/Zn-SnO2 catalyst can be reused at least nine times for the oxidative cleavage of 1-methyl-1-cyclohexene without loss of catalytic performance and can be applied to the oxidation of various other substrate molecules.
- Yoshimura, Yu,Ogasawara, Yoshiyuki,Suzuki, Kosuke,Yamaguchi, Kazuya,Mizuno, Noritaka
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p. 1662 - 1670
(2017/07/22)
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- Rhodium-catalyzed hydroformylation in γ-valerolactone as a biomass-derived solvent
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Rhodium-catalyzed hydroformylation of styrene, α-methylstyrene, dimethyl itaconate, and (R)-limonene was performed in gamma-valerolactone (GVL) as a proposed biomass-based environmentally benign solvent for hydroformylation referring to toluene as a generally used conventional solvent. Both achiral (triphenylphosphine, 1,3-bis(diphenylphoshino)propane) and enantiopure bidentate phosphine ligands ((S,S)-BDPP, (R)-BINAP, (R)-QUINAP, (R,R)-DIOP, (Rc),(Sp)-JOSIPHOS, (S)-SEGPHOS, (S)-(DM)-SEGPHOS) were investigated in in situ generated Rh-diphosphine catalyst systems. In general, the catalysts' activity in GVL was lower than in toluene; however, remarkable chemo- (>99%) and regioselectivities (>95%) were achieved in GVL under identical conditions. The BDPP-modified Rh-catalyst was recycled for three consecutive cycles; however a decrease in its activity was detected.
- Pongrácz, Péter,Bartal, Brigitta,Kollár, László,Mika, László T.
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p. 140 - 145
(2017/09/12)
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- Heck arylation of allyl alcohol catalyzed by Pd(0) nanoparticles
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Pd(0) nanoparticles ca. 2 nm in diameter were obtained by the reduction of PdCl2 and Pd(OAc)2 in water at 80 °C in the presence of a PVP-stabilizing polymer. Pd(0) NPs were successfully used in the Heck coupling of allyl alcohol with iodo- and bromobenzenes. Iodobenzenes reacted under solventless conditions or in DMF solution producing 3-arylpropanals and 2-arylpropanals as the main products. The same products were obtained in the reaction of bromobenzene in TBAB as the reaction medium. The stability of Pd(0) NPs was evidenced in recycling experiments. Similar Heck coupling results were also obtained with the palladium compounds PdCl2(cod) and Pd(OAc)2 under the same conditions.
- Tarnowicz, Stanis?awa,Alsalahi, Waleed,Mieczyńska, Ewa,Trzeciak, Anna M.
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p. 5605 - 5612
(2017/08/26)
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