Photoredox Mediated Synthesis of Substituted Imidazoles from Terminal Alkynes

A visible light photoredox-induced approach for the synthesis of substituted imidazoles via alkynes, glycine methyl ester, and thiophenol is presented. The reaction is driven via photoinduced exploration of alkynes and their combination with thiol, producing vinylic radical and its subsequent nucleophilic addition to glycine methyl ester as N-source to produce imidazoles via concurrent two C─N bond formations.

Abstract

A visible light photoredox-induced approach for the synthesis of substituted imidazoles via alkynes, glycine methyl ester, and thiophenol is presented. The reaction is facilitated by the photoinduced activation of alkynes, coupled with thiol, which generates a vinylic radical. This radical subsequently undergoes a nucleophilic addition to glycine methyl ester, serving as a nitrogen source, thereby leading to the formation of imidazoles through the concurrent creation of two carbon-nitrogen bonds.

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