8-Aminoimidazo[1,2-a]pyridine-Directed Nickel-Catalyzed β-C(sp 2)–H Arylation and Alkylation: Implementation for Late-Stage C–H Activation towards Biologically Relevant Compounds

Published in: Synthesis 2025; 57(14): 2207-2220

DOI: 10.1055/a-2605-1321

Authors: Suman Kumar Joardar [TCGLS Member], Gunturu Prabhakar Rao, Jakkani Soumya [TCGLS Member],Sourasree Midya [TCGLS Member], Ramanand Das, Mrinalkanti Kundu [TCGLS Member]

Abstract: We herein report an efficient and convenient protocol for the Ni(II)-catalyzed ortho-C(sp²)–H arylation as well as alkylation using 8-aminoimidazo[1,2-a]pyridine (8-AIP) as a unique directing group in the absence of any external ligand and oxidant. This protocol is scalable, has excellent yield, exhibits high levels of β-site selectivity, and tolerates a broad spectrum of functional groups. A kinetic study was also undertaken to establish a plausible reaction pathway. Single-crystal XRD analysis was carried out to determine one of the structures. Furthermore, late-stage functionalization of the synthesized derivatives demonstrates the methodology’s synthetic adaptability and showcases the use of 8-AIP as an inbuilt directing group.