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Indexed by:期刊论文

Date of Publication:2018-12-06

Journal:EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Included Journals:SCIE、Scopus

Volume:2018

Issue:45

Page Number:6217-6222

ISSN No.: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.