Construction of Thienopyrroles through Rhodium-Catalyzed Direct Annulation of (Acetylamino)thiophenes with Alkynes

Abstract

The direct annulative coupling of 3-(acetylamino)thiophenes with internal alkynes proceeds smoothly under rhodium catalysis through acetylamino-directed C–H bond cleavage at the C2-position, leading to the effective construction of 4-acetylthieno[3,2-b]pyrrole derivatives. The acetyl directing group on the annulation product is readily removed to produce the 4-unprotected thieno[3,2-b]pyrrole derivative.

Key words

annulation - C–H functionalization - fused heterocycles - rhodium catalysis - thienopyrrole

Publication History

Received: 27 December 2022

Accepted after revision: 18 January 2023

Accepted Manuscript online:
18 January 2023

Article published online:
20 February 2023

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