Thiol substrate-promoted dehydrogenative cyclization of arylmethyl thiols with ortho-substituted amines: a universal approach to heteroaromatic compounds?

Organic Chemistry Frontiers Pub Date: 2019-06-15 DOI: 10.1039/C9QO00554D

Abstract

A thiol substrate-promoted one-pot synthesis of a library of heteroaromatic compounds was developed. Benzo[d]oxazole, benzo[d]thiazole, benzo[d]imidazole, oxazolo[4,5-b]pyridine and naphtho[2,3-d]oxazole derivatives were obtained under metal-free and external oxidant-free conditions in moderate to excellent yields. Commercially available substrates and the absence of supplemental catalysts, oxidants or additives make this method both practical and efficient.

Graphical abstract: Thiol substrate-promoted dehydrogenative cyclization of arylmethyl thiols with ortho-substituted amines: a universal approach to heteroaromatic compounds
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