NiH-Catalyzed Migratory Defluorinative Olefin Cross-Coupling: Trifluoromethyl-Substituted Alkenes as Acceptor Olefins to Form gem-Difluoroalkenes

Fenglin Chen; Xianfeng Xu; Yuli He; Genping Huang; Shaolin Zhu

doi:10.1002/anie.201915840

NiH-Catalyzed Migratory Defluorinative Olefin Cross-Coupling: Trifluoromethyl-Substituted Alkenes as Acceptor Olefins to Form gem-Difluoroalkenes

Angew Chem Int Ed Engl. 2020 Mar 23;59(13):5398-5402. doi: 10.1002/anie.201915840. Epub 2020 Feb 20.

Authors

Fenglin Chen¹, Xianfeng Xu¹, Yuli He¹, Genping Huang², Shaolin Zhu¹

Affiliations

¹ State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Material, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.
² Department of Chemistry, School of Science, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300072, China.

PMID: 31951070
DOI: 10.1002/anie.201915840

Abstract

We report a NiH-catalyzed migratory defluorinative coupling between two electronically differentiated olefins. A broad range of unactivated donor olefins can be joined directly to acceptor olefins containing an electron-deficient trifluoromethyl substituent in both intra- and intermolecular fashion to form gem-difluoroalkenes. This migratory coupling shows both site- and chemoselectivity under mild conditions, with the formation of a tertiary or quaternary carbon center.

Keywords: C−H activation; cross-coupling; isomerization; nickel; regioselectivity.

Publication types

Research Support, Non-U.S. Gov't