121925-53-9Relevant academic research and scientific papers
Photoinduced Copper-Catalyzed Asymmetric Decarboxylative Alkynylation with Terminal Alkynes
Dong, Xiao-Yang,Du, Xuan-Yi,Fang, Jia-Heng,Gu, Qiang-Shuai,Li, Zhong-Liang,Liu, Xin-Yuan,Wang, Li-Lei,Xia, Hai-Dong
supporting information, p. 16926 - 16932 (2020/08/25)
We describe a photoinduced copper-catalyzed asymmetric radical decarboxylative alkynylation of bench-stable N-hydroxyphthalimide(NHP)-type esters of racemic alkyl carboxylic acids with terminal alkynes, which provides a flexible platform for the construction of chiral C(sp3)?C(sp) bonds. Critical to the success of this process are not only the use of the copper catalyst as a dual photo- and cross-coupling catalyst but also tuning of the NHP-type esters to inhibit the facile homodimerization of the alkyl radical and terminal alkyne, respectively. Owing to the use of stable and easily available NHP-type esters, the reaction features a broader substrate scope compared with reactions using the alkyl halide counterparts, covering (hetero)benzyl-, allyl-, and aminocarbonyl-substituted carboxylic acid derivatives, and (hetero)aryl and alkyl as well as silyl alkynes, thus providing a vital complementary approach to the previously reported method.
Enantioselective Decarboxylative Cyanation Employing Cooperative Photoredox Catalysis and Copper Catalysis
Wang, Dinghai,Zhu, Na,Chen, Pinhong,Lin, Zhenyang,Liu, Guosheng
supporting information, p. 15632 - 15635 (2017/11/14)
The merger of photoredox catalysis with asymmetric copper catalysis have been realized to convert achiral carboxylic acids into enantiomerically enriched alkyl nitriles. Under mild reaction conditions, the reaction exhibits broad substrate scope, high yields and high enantioselectivities. Furthermore, the reaction can be scaled up to synthesize key chiral intermediates to bioactive compounds.
Practical synthesis of diethyl phenylsuccinate by Mg-promoted carboxylation of ethyl cinnamate
Maekawa, Hirofumi,Murakami, Taro,Miyazaki, Takeshi,Nishiguchi, Ikuzo
supporting information; experimental part, p. 368 - 369 (2011/05/04)
Mg-promoted reduction of ethyl cinnamate (1a) in the presence of carbon dioxide gave a mixture of β-carboxylated compound 2a and α,β-dicarboxylated compound 3a. Similar reductive carboxylation of 1a followed by acidic decarboxylation of one of the two geminal carboxyl groups of the generated 3a and esterification afforded selective formation of diethyl phenylsuccinate (2a) in good yield.
Electrochemical carboxylation of cinnamate esters in MeCN
Wang, Huan,Zhang, Kai,Liu, Ying-Zi,Lin, Mei-Yu,Lu, Jia-Xing
, p. 314 - 318 (2008/09/16)
Electrochemical carboxylation of cinnamate esters has been carried out by cathodic reduction of C{double bond, long}C bond in an undivided cell equipped with Mg sacrificial anode and using MeCN saturated with CO2 as solvent. The yields and the
HIGHLY REGIOSELECTIVE RING-OPENING OF α-SUBSTITUTED CYCLIC ACID ANHYDRIDES CATALYZED BY LIPASE
Hiratake, Jun,Yamamoto, Kazuyoshi,Yamamoto, Yukio,Oda, Jun'ichi
, p. 1555 - 1556 (2007/10/02)
Lipase Amano P irreversibly catalyzed a ring-opening of α-substituted cyclic acid anhydrides 1 preferentially at the less hindered carbonyl group to give monoesters with high regioselectivity.
