Abstract
A highly efficient heterogeneous gold(I)-catalyzed oxidative cyclization of diynones with alcohols has been developed via a nucleophilic attack to the carbonyl group of the α,α'-dioxo gold carbene and subsequent 1,2-alkynyl migration. The reaction proceeds smoothly in 1,2-dichloroethane at 60 °C by using 8 mol% of MCM-41-anchored sterically demanding NHC-gold(I) complex [MCM-41-IPrAuNTf2] as catalyst and 3,5-dichloropyridine N-oxide as oxidant and provides a general and practical method for the assembly of a wide variety of functionalized furan-3-carboxylates in good to excellent yields. Importantly, this heterogenized gold(I) complex is easy to recover by centrifugation of the reaction mixture and is recyclable up to seven times without any apparent loss of its catalytic activity.
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