6553-80-6Relevant academic research and scientific papers
Cryoelectrochemistry: Electrochemical reduction of 2(RS)-methyl 1-(tert-butoxycarbonyl)-2-iodomethyl-2,5-dihydropyrrole-2-carboxylate
Banks, Craig E.,Evans, Russell G.,Rodrigues, Jason,Turner, Peter G.,Donohoe, Timothy J.,Compton, Richard G.
, p. 2365 - 2372 (2005)
Cryoelectrochemisty with cyclic voltammetry and chronoamperometry has been applied to give an insight into a reductive pyrroline ring opening reaction, and has allowed the number of electrons participating in the reaction to be deduced from potential step experiments.
Alkoxycarbonylation of olefins with carbon dioxide by a reusable heterobimetallic ruthenium-cobalt catalytic system
Zhang, Xuehua,Shen, Chaoren,Xia, Chungu,Tian, Xinxin,He, Lin
supporting information, p. 5533 - 5539 (2019/01/03)
The heterobimetallic ruthenium-cobalt catalytic system exhibited good catalytic performance and reusability in the reductive alkoxycarbonylation of olefins with carbon dioxide. Compared to the previous system only consisting of ruthenium catalyst, the binary catalyst system effectively reduced the usage of noble metal and ionic liquid additives. The respective contribution of ruthenium and cobalt catalysts in this multiple-step catalytic process was investigated by a series of condition-controlled experiments. The evolution of the ruthenium catalyst and the occurrence of alkene hydrogenation during the reaction was explained by theortical calculations.
Oxidative Alkane C?H Alkoxycarbonylation
Lu, Lijun,Shi, Renyi,Liu, Luyao,Yan, Jingwen,Lu, Fangling,Lei, Aiwen
supporting information, p. 14484 - 14488 (2016/10/03)
Directly utilizing a chemical feedstock to construct valuable compounds is an attractive prospect in organic synthesis. In particular, the combination of C(sp3)?H activation and oxidative carbonylation involving alkanes and CO gas is a promising and efficient method to synthesize carbonyl derivatives. However, due to the high C?H bond dissociation energy and low polarity of unactivated alkanes, the carbonylation of unactivated C(sp3)?H bonds still remains a great challenge. In this work, we introduce a palladium-catalyzed radical oxidative alkoxycarbonylation of alkanes to prepare numerous alkyl carboxylates. Various alkanes and alcohols were compatible, generating the desired products in up to 94 % yield. Remarkably, ethane, a constituent of natural gas, could be employed as a substrate under the standard reaction conditions. Preliminary mechanistic studies revealed a probable palladium-catalyzed radical process.
Low-Pressure Radical11C-Aminocarbonylation of Alkyl Iodides through Thermal Initiation
Chow, Shiao Y.,Odell, Luke R.,Eriksson, Jonas
, p. 5980 - 5989 (2016/12/26)
A radical11C-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into11C-labelled amides, including the 11β-HSD1 inhibitor [carbonyl-11C]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated11C-aminocarbonylation, which is limited to the preparation of11C-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon–[11C]CO delivery unit represents a simple and convenient alternative to previous radical11C-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.
Ester Formation via Nickel-Catalyzed Reductive Coupling of Alkyl Halides with Chloroformates
Zheng, Min,Xue, Weichao,Xue, Teng,Gong, Hegui
supporting information, p. 6152 - 6155 (2016/12/09)
The synthesis of alkyl esters from readily available alkyl halides and chloroformates was achieved for the first time using a mild Ni-catalyzed reductive coupling protocol. Unactivated primary and secondary alkyl iodides as well as glycosyl, benzyl, and aminomethyl halides were successfully employed to yield products in moderate to excellent yields with high functional group tolerance.
Nickel-catalyzed dehydrogenative cross-coupling: Direct transformation of aldehydes into esters and amides
Whittaker, Aaron M.,Dong, Vy M.
supporting information, p. 1312 - 1315 (2015/01/30)
By exploring a new mode of nickel-catalyzed cross-coupling, a method to directly transform both aromatic and aliphatic aldehydes into either esters or amides has been developed. The success of this oxidative coupling depends on the appropriate choice of catalyst and organic oxidant, including the use of either α,α,α-trifluoroacetophenone or excess aldehyde. Mechanistic data that supports a catalytic cycle involving oxidative addition into the aldehyde C-H bond is also presented.
Hydroesterification of alkenes with sodium formate and alcohols promoted by cooperative catalysis of Ru3(CO)12 and 2-pyridinemethanol
Kim, Dong-Su,Park, Woo-Jin,Lee, Chang-Hee,Jun, Chul-Ho
, p. 12191 - 12196 (2015/01/09)
(Figure Presented) A chelation-assisted hydroesterification reaction of alkenes with sodium formate and alcohols that involves cooperative catalysis by Ru3(CO)12 and 2-pyridinemethanol is described. In this three-component coupling reaction, sodium formate serves as the carbon monoxide source.
NOVEL PROCESS
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Page/Page column 4, (2009/12/27)
The present invention relates to a process for the preparation of 1-(2-ethyl-butyl)-cyclohexanecarboxylic acid which is useful as an intermediate in the preparation of pharmaceutically active compounds.
A Simple and Efficient Esterification Method
Ming-Yi, Chen,Lee, Adam Shih-Yuan
, p. 103 - 108 (2007/10/03)
A convenient and practical esterification was realized and this reaction proceeded without a dehydrating reagent or water removal equipment. The synthesis of esters by reaction of carboxylic acids with various alcohols such as methyl, ethyl, isopropyl, isobutyl, allyl, benzyl, propargyl and decanyl alcohols were achieved with a catalytic amount of CBr4 under refluxing reaction condition.
Esterification of sterically hindered acids and alcohols in fluorous media
Gacem, Badra,Jenner, Gérard
, p. 1391 - 1393 (2007/10/03)
Sterically hindered esterification reactions are best performed in specific fluorous media in the presence of catalytic amounts of diphenylammonium triflate. Fluorous media, in addition to their positive effect on yields, have inherent favorable properties respecting environment and permitting simple work-up. Highly congested reagents, however, react only marginally.
