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双功能铜催化剂诱导的烯烃基于二氟卡宾的氰基二氟甲基化反应

Difluorocarbene-based cyanodifluoromethylation of alkenes induced by a dual-functional Cu-catalyst.

作者信息

Zhang Min, Lin Jin-Hong, Jin Chuan-Ming, Xiao Ji-Chang

机构信息

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Department of Chemistry and Chemical Engineering, Hubei Normal University, 11 Cihu Road, Huangshi, 435002, Hubei, China.

出版信息

Chem Commun (Camb). 2021 Mar 11;57(21):2649-2652. doi: 10.1039/d1cc00160d.

DOI:10.1039/d1cc00160d
PMID:33587731
Abstract

Although cyanofluoroalkylation has received increasing attention, a toxic cyanation reagent is usually required. Herein, a Cu-catalyzed difluorocarbene-based cyanodifluoromethylation of alkenes with BrCF2CO2Et/NH4HCO3 under photocatalytic conditions is described. BrCF2CO2Et and NH4HCO3 serve as a carbon source and a nitrogen source of the nitrile group, respectively, avoiding the use of a stoichiometric toxic cyanation reagent. The Cu-complex plays a dual role. It is not only a photocatalyst, but also a coupling catalyst for the formation of a C-CN bond.

摘要

尽管氰基氟烷基化已受到越来越多的关注,但通常需要使用有毒的氰化试剂。本文描述了在光催化条件下,铜催化的烯烃与BrCF₂CO₂Et/NH₄HCO₃进行基于二氟卡宾的氰基二氟甲基化反应。BrCF₂CO₂Et和NH₄HCO₃分别作为腈基的碳源和氮源,避免了使用化学计量的有毒氰化试剂。铜配合物起着双重作用。它不仅是光催化剂,也是形成C-CN键的偶联催化剂。

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