Premium
Divergent Regio‐ and Stereoselective Gold‐catalyzed Synthesis of α‐Fluorosulfones and β‐Fluorovinylsulfones from Alkynylsulfones
Author(s) -
Zeng Xiaojun,
Liu Shiwen,
Hammond Gerald B.,
Xu Bo
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703179
Subject(s) - stereoselectivity , sulfone , catalysis , carbene , oxide , chemistry , combinatorial chemistry , functional group , organic chemistry , polymer
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.