Regioselective Vinylation of Remote Unactivated C(sp3)−H Bonds: Access to Complex Fluoroalkylated Alkenes. Issue 5 (28th December 2018)

• Record Type: Journal Article
• Authors: Wu, Shuo; Wu, Xinxin; Wang, Dongping; Zhu, Chen
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 5(2019)
• Page Start: 1499
• Page End: 1503
• Publication Date: 2018-12-28
• Subjects: alcohols -- C−H activation -- fluorine -- photocatalysis -- radicals; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201812927
• Languages: English
• ISSNs: 1433-7851

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. Abstract : Give and take : Regioselective incorporation of a particular functional group into aliphatic sites by direct activation of unreactive C−H bonds remains challenging. Herein a new protocol for the regioselective vinylation of unactivated C(sp 3 )−H bonds is reported. The activation of a remote C(sp 3 )−H bond is promoted by a C‐centered radical instead of the commonly used N and O radicals.