In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and triethylamine, 3-(trimethylsilyl)propargyl carboxylates undergo a one-pot alkylation-cyclization- desilylation reaction with ketones to produce 2-methylfurans. Alkylation at 0 °C in methylene chloride, followed by acid-catalyzed cyclization at room temperature, provides the furans in 52-86% yield. Cyclization and desilylation appear to be promoted by triflic acid generated in situ from the exposure of the reaction mixture to water upon completion of the initial substitution reaction.
Copyright © 2021, Tetrahedron Letters.
Danielle E. Sklar, Alex V. Helbling, Yiqi Liu, C. Wade Downey. One-Pot Synthesis of 2-Methylfurans from 3-(Trimethylsilyl)propargyl Acetates Promoted by Trimethylsilyl Trifluoromethanesulfonate. Tetrahedron Letters 2021, 87, Article 153424.