A Method for Pyrrole Synthesis through Intramolecular Cyclization of γ-Alkynyl Oximes Promoted by SmI₂

Abstract

A new strategy for the synthesis of pyrrole through intramolecular cyclization of γ-alkynyl oximes promoted by SmI₂ is reported for the first time. In contrast to the prior methods, the selection of oxime instead of oxime ether or ester as substrate makes the synthetic method without accompaniment of organic waste (ArCO₂H, AcOH, or ROH) because the hydroxyl group in oxime acts as the leaving group and is finally removed in the form of water molecule in the reaction. From a synthetic point of view, a series of pyrroles were obtained in this one-pot reaction with a broad scope of substrates and feasible reaction conditions.

Key words

pyrrole - γ-alkynyl - oxime - SmI₂ - N-centered radical - atomic economic

Publication History

Received: 13 May 2022

Accepted: 29 August 2022

Accepted Manuscript online:
29 August 2022

Article published online:
22 September 2022

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