Nickel-Catalyzed 8-Aminoimidazo[1,2-a]pyridine-Assisted C(sp²)–H Alkynylation of (Hetero)arenes via an Inverse Sonogashira Strategy Suitable for Late-Stage Modification

Abstract

An efficient and convenient approach for the Ni(II)-catalyzed ortho-C(sp²)–H alkynylation, using 8-aminoimidazo[1,2-a]pyridine (8-AIP) as a directing group in the absence of any ligand and oxidant, is described here. The developed protocol represents an Ni(II)-catalyzed route to a broad spectrum of alkynylbenzamides, ensuring site selectivity and diverse functional group compatibility. Various control experiments were performed to underpin the mechanistic pathway. Moreover, late-stage modifications of the synthesized derivatives are demonstrated to reveal the efficacy of 8-AIP as a useful directing group.

Keywords

C–H activation - Ni catalysis - 8-AIP - β-C(sp²)–H alkynylation - LSF

Publication History

Received: 07 November 2025

Accepted after revision: 18 December 2025

Accepted Manuscript online:
19 December 2025

Article published online:
13 February 2026

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