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Regioselective Vinylation of Remote Unactivated C(sp3 )-H Bonds: Access to Complex Fluoroalkylated Alkenes
Shuo Wu1, Xinxin Wu1, Dongping Wang1
1Key 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.
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(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.
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