Synthesis of 2-Aminobenzo[b]thiophenes via an Intramolecular Dehydrogenative C–S Bond Formation Effected by Iodine(III) Reagents

Abstract

A direct synthesis of medicinal chemistry-relevant 2-aminobenzo[b]thiophenes has been achieved from substituted thioamides of 2-arylacetic acids through a fast intramolecular cross-dehydrogenative cyclization, mediated by hydroxy(tosyloxy)iodobenzene (HTIB, Koser’s reagent). This synthetic approach is operationally simple, uses easily accessible substrates, and tolerates a variety of substituents at different sites, providing an opportunity for diversification.

Key words

C–S bond formation - hypervalent iodine - benzo[b]thiophenes - metal free - oxidative cyclization - thioamides - C–H functionalization

Publication History

Received: 13 November 2024

Accepted after revision: 11 December 2024

Accepted Manuscript online:
11 December 2024

Article published online:
20 January 2025

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