Tandem Difluoroalkylation-Arylation of Enamides Catalyzed by Nickel

Ji-Wei Gu; Qiao-Qiao Min; Ling-Chao Yu; Xingang Zhang

doi:10.1002/anie.201606458

Tandem Difluoroalkylation-Arylation of Enamides Catalyzed by Nickel

Angew Chem Int Ed Engl. 2016 Sep 26;55(40):12270-4. doi: 10.1002/anie.201606458. Epub 2016 Sep 8.

Authors

Ji-Wei Gu¹, Qiao-Qiao Min¹, Ling-Chao Yu¹, Xingang Zhang²

Affiliations

¹ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
² Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China. xgzhang@mail.sioc.ac.cn.

PMID: 27605485
DOI: 10.1002/anie.201606458

Abstract

A nickel-catalyzed three-component reaction for the synthesis of difluoroalkylated compounds through tandem difluoroalkylation-arylation of enamides has been developed. The reaction tolerates a variety of arylboronic acids and widely available difluoroalkyl bromides, and even the relatively inert substrate chlorodifluoroacetate. The significant advantages of this protocol are the low-cost nickel catalyst, synthetic convenience, excellent functional-group compatibility and high reaction efficiency.

Keywords: boron; cross-coupling; fluorine; nickel; synthetic methods.

Publication types

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