Palladium-Catalyzed Fluorosulfonylvinylation of Organic Iodides

Gao-Feng Zha; Qinheng Zheng; Jing Leng; Peng Wu; Hua-Li Qin; K Barry Sharpless

doi:10.1002/anie.201701162

Palladium-Catalyzed Fluorosulfonylvinylation of Organic Iodides

Angew Chem Int Ed Engl. 2017 Apr 18;56(17):4849-4852. doi: 10.1002/anie.201701162. Epub 2017 Mar 29.

Authors

Gao-Feng Zha¹, Qinheng Zheng², Jing Leng¹, Peng Wu³, Hua-Li Qin¹, K Barry Sharpless²

Affiliations

¹ State Key Laboratory of Silicate Materials for Architectures, and School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan, 430070, China.
² Department of Chemistry, The Scripps Research Institute, La Jolla, CA, 92037, USA.
³ Department of Chemical Physiology, The Scripps Research Institute, La Jolla, CA, 92037, USA.

Abstract

A palladium-catalyzed fluorosulfonylvinylation reaction of organic iodides is described. Catalytic Pd(OAc)₂ with a stoichiometric amount of silver(I) trifluoroacetate enables the coupling process between either an (hetero)aryl or alkenyl iodide with ethenesulfonyl fluoride (ESF). The method is demonstrated in the successful syntheses of eighty-eight otherwise difficult to access compounds, in up to 99 % yields, including the unprecedented 2-heteroarylethenesulfonyl fluorides and 1,3-dienylsulfonyl fluorides.

Keywords: alkenes; click chemistry; drug discovery; fluorine; palladium.

Publication types

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

Grants and funding

R01 GM117145/GM/NIGMS NIH HHS/United States