Palladium-Catalyzed Fluoroarylation of gem-Difluoroalkenes

Hai-Jun Tang; Ling-Zhi Lin; Chao Feng; Teck-Peng Loh

doi:10.1002/anie.201705321

Palladium-Catalyzed Fluoroarylation of gem-Difluoroalkenes

Angew Chem Int Ed Engl. 2017 Aug 7;56(33):9872-9876. doi: 10.1002/anie.201705321. Epub 2017 Jul 13.

Authors

Hai-Jun Tang¹, Ling-Zhi Lin¹, Chao Feng¹, Teck-Peng Loh²

Affiliations

¹ Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University, 30 South Puzhu Road, Nanjing, 211816, P.R. China.
² Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371, Singapore.

PMID: 28646533
DOI: 10.1002/anie.201705321

Abstract

A Pd-catalyzed fluoroarylation of gem-difluoroalkenes with aryl halides is reported. By taking advantage of the in situ generated α-CF₃ -benzylsilver intermediates derived from the nucleophilic addition of silver fluoride to gem-difluoroalkenes, this strategy bypasses the use of a strong base, thus enabling a mild and general synthetic method for ready access to non-symmetric α,α-disubstituted trifluoroethane derivatives.

Keywords: arylation; cross-coupling; fluorination; gem-difluoroalkenes; palladium.

Publication types

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