Release Time:2019-03-13  Hits:

Indexed by: Journal Article

Date of Publication: 2018-12-06

Journal: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Included Journals: Scopus、SCIE

Volume: 2018

Issue: 45

Page Number: 6217-6222

ISSN: 1434-193X

Key Words: Fluorine; Ketones; Domino reactions; Trifluoromethyl alkenyl triflates

Abstract: A method for the synthesis of beta-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.