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Highly Stereoselective and One‐Pot Synthesis of Tetra‐substituted Monofluoroalkenes with Aldehydes and Fluorobis(phenylsulfonyl)methane
Author(s) -
Shen Xiao,
Ni Chuanfa,
Hu Jinbo
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201300365
Subject(s) - chemistry , stereoselectivity , tetra , sulfonyl , methane , cinnamaldehyde , aryl , sulfone , organic chemistry , medicinal chemistry , catalysis , alkyl
A highly stereoselective synthesis of tetrasubstituted monofluoroalkenes with aldehydes and fluorobis(phenylsulfonyl)methane (FBSM) in one pot has been developed. The reaction was amenable to para ‐ and meta ‐substituted aryl aldehydes, 2‐naphthaldehyde, and cinnamaldehyde, giving phenylsulfonyl‐substituted monofluoroalkenes in 40%–86% yields with 98/2–99/1 Z / E ratios. The presence of the sulfonyl group enables the further transformation of the products into more useful monofluoroalkenes.