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钴催化的氟化仲苄基溴与芳基硼酸锂/ZnBr 的不对称交叉偶联反应。

Cobalt-Catalyzed Asymmetric Cross-Coupling Reaction of Fluorinated Secondary Benzyl Bromides with Lithium Aryl Boronates/ZnBr.

机构信息

Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

出版信息

Org Lett. 2020 Jun 5;22(11):4327-4332. doi: 10.1021/acs.orglett.0c01363. Epub 2020 May 20.

Abstract

A cobalt-catalyzed asymmetric cross-coupling of α-bromo-α-fluorotoluene derivatives with a variety of aryl zincates derived from lithium aryl -butyl pinacol boronates and ZnBr under mild reaction conditions was described. In addition to mild reaction conditions, another advantage includes the compatibility of various common functional groups such as fluoride, chloride, bromide, cyano, or ester groups. Furthermore, this protocol was successfully applied to the enantioselective synthesis of three fluorinated derivatives of biologically active compounds or drug molecules.

摘要

钴催化的α-溴-α-氟代甲苯衍生物与各种芳基锌试剂的不对称交叉偶联反应被描述,这些芳基锌试剂是由锂芳基-丁基频哪醇硼酸酯和 ZnBr 在温和的反应条件下衍生而来。除了温和的反应条件外,另一个优点还包括各种常见官能团的兼容性,如氟、氯、溴、氰基或酯基。此外,该方案还成功地应用于三种具有生物活性化合物或药物分子的氟化衍生物的对映选择性合成。

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