Cascade Synthesis of Benzimidazole-Linked Pyrroles via Copper Catalyzed Oxidative Cyclization and Ketonization

Tzuen Yang Ye, Manikandan Selvaraju, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

A three-component cascade reaction of 2-aminobenzimidazole, aldehyde, and terminal alkyne has been explored for an efficient synthesis of benzimidazole-linked tetrasubstituted pyrroles. The reaction sequence involves the formation of propargylamine, insertion of a terminal alkyne, and a ring opening reaction followed by an intramolecular carbonylative cyclization under aerobic conditions. It represents a novel strategy to the construction of C=N, C=C, C=O bonds and a new five-membered 2-ketopyrrole ring. In this process, the reaction conditions are crucial and an attempt to elucidate the novel reaction pathway is well supported by X-ray crystallography.

Original languageEnglish
Pages (from-to)3103-3106
Number of pages4
JournalOrganic Letters
Volume19
Issue number12
DOIs
StatePublished - 16 Jun 2017

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