Regioselective Vinylation of Remote Unactivated C(sp3 )@H Bonds: Access to Complex Fluoroalkylated Alkenes

Shuo Wu⁺ , Xinxin Wu⁺ , Dongping Wang, and Chen Zhu^*（朱晨）

Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science, Soochow University 199 Ren-Ai Road, Suzhou, Jiangsu 215123 (China)

^{[ + ]} These authors contributed equally to this work.

Angew. Chem. Int. Ed.2019, 58, 1499 --1503

Regioselective incorporation of a particular functional group into aliphatic sites by direct activation of unreactive C−H bonds is of great synthetic value. Despite advances in radical‐mediated functionalization of C(sp³)−H bonds by a hydrogen‐atom transfer process, the site‐selective vinylation of remote C(sp³)−H bonds still remains underexplored. Reported herein is a new protocol for the regioselective vinylation of unactivated C(sp³)−H bonds. The remote C(sp³)−H activation is promoted by a C‐centered radical instead of the commonly used N and O radicals. The reaction possesses high product diversity and synthetic efficiency, furnishing a plethora of synthetically valuable E alkenes bearing tri‐/di‐/mono‐fluoromethyl and perfluoroalkyl groups.

链接：https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201812927