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光氧化还原/镍双催化钾硫甲基三氟硼酸盐与芳基和杂芳基溴化物的交叉偶联反应。

Photoredox/Nickel Dual Catalytic Cross-Coupling of Potassium Thiomethyltrifluoroborates with Aryl and Heteroaryl Bromides.

机构信息

Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.

出版信息

J Org Chem. 2021 May 7;86(9):6937-6942. doi: 10.1021/acs.joc.1c00347. Epub 2021 Apr 28.

Abstract

The cross-coupling of -aryl and -alkyl potassium thiomethyltrifluoroborates with aryl and heteroaryl bromides is reported via photoredox/nickel dual catalysis. The transformation is achieved under mild conditions with commercially available or readily prepared, air stable reagents and affords benzylthioether products in moderate to good yields with good functional group tolerance. A practical and improved synthesis of potassium thiomethyltrifluoroborates is also reported that affords access to previously undescribed reagents.

摘要

通过光氧化还原/镍双催化作用,报道了-芳基和-烷基硫甲基三氟硼酸钾与芳基和杂芳基溴化物的交叉偶联。该转化在温和条件下,使用商业上可获得的或易于制备的、空气稳定的试剂进行,以中等至良好的收率提供苄基硫醚产物,对官能团具有良好的耐受性。还报道了一种实用且改进的硫甲基三氟硼酸钾的合成方法,该方法提供了以前未描述的试剂。

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