<i>N</i>-Heterocyclic Carbene-Catalyzed Cyclization of Aldehydes with α-Diazo Iodonium Triflate: Facile Access to 2,5-Disubstituted 1,3,4-Oxadiazoles

Abstract

Herein, we report a novel organocatalytic process for synthesis of complex 1,3,4-oxadiazoles from readily accessible aldehydes. By exploiting the nucleophilicity of the putative Breslow intermediate and the inherent electrophilicity of α-diazo iodonium triflate, we have found that N-heterocyclic carbene catalyst promotes efficient cyclization of various aldehydes and α-diazo iodonium triflates. The reaction proceeds under mild conditions with a wide range of functional group tolerance. The heterocyclic products can be readily further functionalized, rendering the protocol highly valuable.