Electrochemical Dehydrogenative C−H Aminomethylation of Imidazopyridines and Related Heterocycles

Abstract

A facile and environmentally friendly electrochemical protocol is herein reported for the C(sp 2 )À C(sp 3 ) cross dehydrogenative coupling between imidazopyridines and N,N-dimethylanilines. The broad functional group compatibility includes halogens, ester, alcohol, sulfone as well as thiophene. This methodology is also suitable for benzo [d]imidazo[2,1-b]thiazole, thiazoimidazole and tetrahydroisoquinoline, and can be scaled up to 5 mmol. Mechanistic insights are discussed.

Multicomponent Cross-Dehydrogenative Coupling of Imidazo[1,2-a]pyridine: Access to Abnormal Mannich and Mannich-Type Reaction

“…Paturea et al in 2022 revealed an electrochemical system for amino methylation of imidazopyridine (Scheme d). In all of the cases, the substrate scope of N , N -dialkyl anilines was limited to para -substituted N , N -dimethylanilines . Notably, in 2022, Li and Wang’s group reported an electrochemical approach for C3-amino methylation with secondary N -methyl amines and para-substituted C3-aryl methylation with tertiary N -methylaniline (Scheme e) .…”

Direct Synthesis of β-Amino Boronates via Amide α-C–H Bond Activation and C(sp3)–C(sp3) Coupling under Dual Ni/Photoredox Catalysis

“…8 More recently, the Huang group developed an innovative metal-free photocatalytic system for coupling alkyl halides with sterically congested tertiary amines. 9 Furthermore, the Yu group disclosed a C(sp 3 )−C(sp 3 ) formation method with the utilization of palladium as the sole catalyst, but only N-aryl tetrahydroisoquinolines were studied. 10 Despite those advancements, the field of amino α-C−H bond alkylation with functionalized alkyl structures continues to require a more substantial development.…”