Rhodium-Catalyzed Direct Vinylene Annulation of 2-Aryloxazolines and Cascade Ring-Opening Using a Vinyl Selenone

Abstract

Over the past two decades, transition-metal-catalyzed C–H activation and the subsequent oxidative cyclization with alkynes or their surrogates has emerged as a powerful synthetic tool for fused heteroaromatics. We report a Rh(III)-catalyzed annulation and ring-opening cascade reaction with 2-aryloxazolines. By utilizing a vinyl selenone as an oxidizing acetylene surrogate, the target three-component coupling products were obtained in high yields without using a stoichiometric amount of external oxidant.

Key words

C–H bond activation - oxazolines - annulation - rhodium catalysis - vinylselenones - cascade reaction

Publication History

Received: 25 October 2023

Accepted after revision: 20 November 2023

Accepted Manuscript online:
20 November 2023

Article published online:
14 December 2023

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