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Metal-Free Catalyzed Regioselective Allylic Trifluoromethanesulfonylation of Aromatic Allylic Alcohols with Sodium Trifluoromethanesulfinate

Authors :
Wanqing Wu
Xiaodong Tang
Zhenming Zhang
Wei Guo
Jianhua Liao
Huanfeng Jiang
Source :
The Journal of Organic Chemistry. 81:1304-1309
Publication Year :
2016
Publisher :
American Chemical Society (ACS), 2016.

Abstract

An efficient procedure for the preparation of allylic trifluoromethanesulfones with high regioselectivity from aromatic allylic alcohols/esters and NaSO2CF3 under transition-metal-free conditions is described. A wide range of functional groups were tolerated. This is the first example to realize different types of allylic alcohols, including primary, secondary, and tertiary allylic alcohols, all of which transferred to the corresponding products efficiently in good to excellent yields with readily available and inexpensive NaSO2CF3. The synthetic utility of the method was demonstrated by performing the reaction at gram scale.

Details

ISSN :
15206904 and 00223263
Volume :
81
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....2658259f5a6f5e3222f4af04c21169cb
Full Text :
https://doi.org/10.1021/acs.joc.5b02674