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单 C-F 转化的 - 氢硅基苯并三氟化物与三苯甲基化合物作为一体化试剂。

Single C-F Transformations of -Hydrosilyl Benzotrifluorides with Trityl Compounds as All-in-One Reagents.

机构信息

Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.

出版信息

Org Lett. 2020 Dec 4;22(23):9292-9297. doi: 10.1021/acs.orglett.0c03529. Epub 2020 Nov 12.

Abstract

A facile method to prepare difluoromethylenes, including α,α-difluorobenzyl chlorides, by single C-F transformations of benzotrifluorides is disclosed. The C-F cleavage followed by chlorination proceeded smoothly using trityl chloride through the generation of trityl cation as an activator and chloride anion as a nucleophile. Diverse difluoromethylenes such as difluorobenzyl ethers were efficiently prepared by virtue of the good versatility of the resulting chloro and fluorosilyl groups.

摘要

本文公开了一种通过苯并三氟化物的单 C-F 转化来制备二氟亚甲基的简便方法,包括α,α-二氟苄基氯。通过使用三苯甲基氯作为活化剂和氯离子作为亲核试剂生成三苯甲基阳离子,C-F 键的断裂和氯化反应顺利进行。由于所得氯代和氟硅基的良好通用性,各种二氟亚甲基,如二氟苄基醚,都可以有效地制备。

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