Regioselective Vinylation of Remote Unactivated C(sp3)−H Bonds: Access to Complex Fluoroalkylated Alkenes. (28th December 2018)

• Record Type: Journal Article
• Authors: Wu, Shuo; Wu, Xinxin; Wang, Dongping; Zhu, Chen
• Is Part Of: Angewandte Chemie. Volume 131:Number 5(2019)
• Page Start: 1513
• Page End: 1517
• Publication Date: 2018-12-28
• Subjects: Alkohole -- C-H-Aktivierung -- Fluor -- Photokatalyse -- Radikale; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201812927
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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(sp 3 )−H bonds by a hydrogen‐atom transfer process, the site‐selective vinylation of remote C(sp 3 )−H bonds still remains underexplored. Reported herein is a new protocol for the regioselective vinylation of unactivated C(sp 3 )−H bonds. The remote C(sp 3 )−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.