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镍催化未活化烯烃的不对称还原芳基苄基化反应

Nickel-Catalyzed Asymmetric Reductive Arylbenzylation of Unactivated Alkenes.

作者信息

Jin Youxiang, Yang Haobo, Wang Chuan

机构信息

Hefei National Laboratory for Physical Science at the Microscale, Department of Chemistry, Center for Excellence in Molecular Synthesis, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P.R. China.

School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, P.R. China.

出版信息

Org Lett. 2020 Apr 3;22(7):2724-2729. doi: 10.1021/acs.orglett.0c00688. Epub 2020 Mar 23.

Abstract

Herein, we report a nickel-catalyzed asymmetric two-component reductive dicarbofunctionalization of aryl iodide-tethered unactivated alkenes using benzyl chlorides as the challenging coupling partner. This arylbenzylation reaction enables the efficient synthesis of diverse benzene-fused cyclic compounds bearing a quaternary stereocenter with a high tolerance of sensitive functionalities in highly enantioselective manner. The preliminary mechanistic investigations suggest a radical chain reaction mechanism.

摘要

在此,我们报道了一种镍催化的、以苄基氯作为具有挑战性的偶联伙伴,对芳基碘连接的未活化烯烃进行不对称双组分还原二碳官能化反应。这种芳基苄基化反应能够以高对映选择性的方式,高效合成多种带有季碳立体中心且对敏感官能团具有高耐受性的苯并稠环化合物。初步的机理研究表明其为自由基链式反应机理。

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