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The study explores a nickel-catalyzed method for selective C(sp2)–H alkynylation using a directing group.

December 21, 2025Synthesis0 citations

Nickel-Catalyzed 8-Aminoimidazo1,2-apyridine Assisted C(sp2)–H Alkynylation of (Hetero)arenes via an Inverse Sonogashira Strategy Suitable for Late-stage Modification

SJS. JOARDARNational Institute of Technology Sikkim GRG. Prabhakar RaoNational Institute of Technology Sikkim JSJ. LAKSHMI CH. SOUMYANational Institute of Technology Sikkim

Key Points

The study explores a nickel-catalyzed method for selective C(sp2)–H alkynylation using a directing group.
Ni(II)-catalyzed ortho-C(sp2)-H alkynylation without ligands or oxidants.
Protocol developed for a variety of alkynylbenzamides.
Control experiments to investigate the mechanistic pathway.
Demonstrated site selectivity in the alkynylation process.
Showed diverse functional group compatibility in the synthesized compounds.
Validated the efficacy of 8-AIP as a directing group for late-stage modifications.

Abstract

Abstract An efficient and convenient approach for the Ni(II)-catalyzed ortho-C(sp2)-H alkynylation using 8-aminoimidazo1,2-a pyridine (8-AIP) as a directing group in the absence of any ligand and oxidant is described here. The developed protocol represents Ni(II)-catalyzed route to a broad spectrum of alkynylbenzamides, ensures 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.

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