2010•SynthesisRequires access

Noncatalytic Electrophilic Oxyalkylation of Some Five-Membered Heterocycles with 2-(Trifluoroacetyl)-1,3-azoles

Pavel K. Mykhailiuk, Pavel V. Khodakovskiy, Dmitriy M. Volochnyuk, Andrey A. Tolmachev

Abstract

A set of electrophilic 2-(trifluoroacetyl)-1,3-azoles demonstrated excellent activity in the C-oxyalkylation of pyrrole, furan, thiophene, 1,3-thiazole, and 1,2-oxazole derivatives. The reaction conditions and the yields of the corresponding trifluoromethyl-substituted alcohols depend strongly on both the electronic and steric nature of the 1,3-azole unit.

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Key concepts: Chemistry, Oxazole, Electrophile, Thiophene, Steric effects, Azole, Thiazole, Pyrrole