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Base‐Promoted Double‐Bond‐Migration/Hydrolysis/Isomerization of 4‐Aryl‐1,1,1‐trifluorobut‐2‐en‐2‐yl Trifluoromethanesulfonates: A Metal‐Free Approach to β‐Trifluoromethyl Ketones
Author(s) -
Zhou Yuhan,
Zhang Chunxia,
Zhao Yilong,
Li Dong,
Zhao Jinfeng,
Wang Zhaotian,
Qu Jingping
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801025
Subject(s) - chemistry , trifluoromethyl , isomerization , aryl , alkoxy group , hydrolysis , medicinal chemistry , double bond , alkyl , base (topology) , bond cleavage , organic chemistry , catalysis , mathematical analysis , mathematics
A method for the synthesis of β‐trifluoromethyl ketones promoted by a base is described. In the presence of DBU, 1‐aryl‐4,4,4‐trifluoromethylbutanones with various functional groups were obtained through the reaction of 4‐aryl‐1,1,1‐trifluorobut‐2‐en‐2‐yl trifluoromethanesulfonates with water in moderate to excellent yields. The reaction underwent a double‐bond‐migration/hydrolysis/isomerization pathway, and 1‐aryl‐4,4,4‐trifluorobut‐2‐en‐1‐ols were determined as the key intermediates. Both electron‐withdrawing and electron‐donating groups, such as fluoro, chloro, bromo, ester, cyano, trifluoromethyl, alkyl, and alkoxy, were tolerated well in this reaction.