Selective single C-F bond arylation of trifluoromethylalkene derivatives

Luning Tang; Ze-Yao Liu; Wenzhi She; Chao Feng

doi:10.1039/c9sc01966a

Selective single C-F bond arylation of trifluoromethylalkene derivatives

Chem Sci. 2019 Aug 5;10(37):8701-8705. doi: 10.1039/c9sc01966a. eCollection 2019 Oct 7.

Authors

Luning Tang¹, Ze-Yao Liu¹, Wenzhi She¹, Chao Feng¹

Affiliation

¹ Institute of Advanced Synthesis , School of Chemistry and Molecular Engineering , Nanjing Tech University , Nanjing 211816 , P. R. China . Email: iamcfeng@njtech.edu.cn.

Abstract

A strategically novel single C-F bond functionalization of CF₃-derived molecules, which shows a prominent advantage for the expedient construction of difluoromethylene-bridged organic scaffolds, is disclosed. The reported protocol consists of S_N2' amination, N-alkylation and palladium-catalyzed allylic substitution reactions, which enables straightforward arylation and alkenylation of vinyltrifluoromethane derivatives. Furthermore, this strategy is characterized by its broad substrate scope with respect to both CF₃-alkene and arylboronic acid derivatives.