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通过镍催化的交叉电子亲核试剂偶联实现非活化烯烃的对映选择性三组分氟烷基化反应。

Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins through Nickel-Catalyzed Cross-Electrophile Coupling.

机构信息

State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai 201620, China.

出版信息

J Am Chem Soc. 2020 May 27;142(21):9604-9611. doi: 10.1021/jacs.0c03708. Epub 2020 May 14.

Abstract

A nickel-catalyzed, enantioselective, three-component fluoroalkylarylation of unactivated alkenes with aryl halides and perfluoroalkyl iodides has been described. This cross-electrophile coupling protocol utilizes a chiral nickel/BiOx system as well as a pendant chelating group to facilitate the challenging three-component, asymmetric difunctionalization of unactivated alkenes, providing direct access to valuable chiral β-fluoroalkyl arylalkanes with high efficiency and excellent enantioselectivity. The mild conditions allow for a broad substrate scope as well as good functional group toleration.

摘要

一种镍催化、对映选择性的三组分反应,可实现未活化的烯烃与芳基卤化物和全氟碘代烷的氟烷基芳基化反应。这种交叉电偶联反应方案利用手性镍/氧化铋体系以及一个侧挂螯合基团,促进了未活化烯烃的具有挑战性的三组分不对称双官能化反应,以高效和优异的对映选择性直接得到有价值的手性β-氟烷基芳基烷烃。温和的反应条件允许广泛的底物范围以及良好的官能团耐受性。

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