Gold-Catalyzed Oxidative Cyclization Involving Nucleophilic Attack to the Keto Group of α,α'-Dioxo Gold Carbene and 1,2-Alkynyl Migration: Synthesis of Furan-3-carboxylates.

Abstract

A multicomponent strategy for the synthesis of functionalized furan-3-carboxylates based on gold-catalyzed oxidative cyclization of diynones with alcohols or water has been developed. Mechanistic studies revealed that a rare nucleophilic attack to the carbonyl group of the α,α'-dioxo gold carbene instead of the carbene center and 1,2-alkynyl group migration were involved in this transformation. This method offers several advantages such as mild conditions, high regio- and chemoselectivity, and wide functional group compatibility.