Divergent Regio- and Stereoselective Gold-catalyzed Synthesis of α-Fluorosulfones and β-Fluorovinylsulfones from Alkynylsulfones

Xiaojun Zeng; Shiwen Liu; Gerald B Hammond; Bo Xu

doi:10.1002/chem.201703179

Divergent Regio- and Stereoselective Gold-catalyzed Synthesis of α-Fluorosulfones and β-Fluorovinylsulfones from Alkynylsulfones

Chemistry. 2017 Sep 4;23(49):11977-11981. doi: 10.1002/chem.201703179. Epub 2017 Aug 16.

Authors

Xiaojun Zeng¹, Shiwen Liu¹, Gerald B Hammond², Bo Xu¹

Affiliations

¹ College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai, 201620, P. R. China.
² Department of Chemistry, University of Louisville, Louisville, KY, 40292, USA.

PMID: 28736856
DOI: 10.1002/chem.201703179

Abstract

We developed a widely applicable, highly efficient synthesis of α-fluorosulfone and β-fluorovinylsulfone catalyzed by gold. Starting with alkynyl sulfone 1, an [Au]/HF/N-oxide system gives α-fluorosulfone 3 via a gold carbene intermediate, and, if no N-oxide is used, direct addition of HF to 1 gives vinyl sulfone 4 via a vinylfluoro gold intermediate. Both methods have good functional group tolerance and the reactions can be conducted in ambient atmosphere.

Keywords: N-oxides; carbenes; fluorination; gold; α-fluorosulfone.