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铑催化的 1-芳基异喹啉衍生物与吲嗪的轴手性 C-H/C-H 交叉偶联反应。

Rhodium-Catalyzed Atroposelective C-H/C-H Cross-Coupling Reaction between 1-Aryl Isoquinoline Derivatives and Indolizines.

机构信息

Chang-Kung Chuang Institute, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China.

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.

出版信息

Org Lett. 2022 Jan 21;24(2):564-569. doi: 10.1021/acs.orglett.1c04002. Epub 2022 Jan 5.

Abstract

A rhodium-catalyzed asymmetric oxidative C-H/C-H cross-coupling reaction between 1-aryl isoquinolines and indolizines is disclosed. With a matched pair of SCpRh complex and chiral carboxylic acid, enantioselective two-fold C-H/C-H cross-coupling reactions between 1-aryl isoquinolines and indolizines provide a variety of axially chiral bi(hetero)aryls in excellent yields and enantioselectivity (up to 96% yield and 98% ee). Mechanistic studies suggest that both C-H cleavages are likely reversible.

摘要

铑催化的 1-芳基异喹啉和吲哚嗪之间的不对称氧化 C-H/C-H 交叉偶联反应被披露。通过匹配的 SCpRh 配合物和手性羧酸,1-芳基异喹啉和吲哚嗪之间的对映选择性两倍 C-H/C-H 交叉偶联反应以优异的收率和对映选择性(高达 96%的收率和 98%的 ee)提供了各种轴向手性双(杂)芳基。机理研究表明,两种 C-H 断裂都可能是可逆的。

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