title: N-Mannich Bases of Aromatic Heterocyclic Amides: Synthesis via Copper-Catalyzed Aerobic Cross-Dehydrogenative Coupling under Ambient Conditions.
abstract: An efficient and facile method to synthesize N-Mannich bases has been developed using an inexpensive copper(I) bromide/air catalyst system at ambient temperature. A cross-dehydrogenative coupling of N,N-dimethylarylamines occurs efficiently with aromatic heterocyclic amides (oxindoles, isatins), cyclic amides (lactams), simple amides (benzamide), as well as imides (succinimide, phthalimide) to furnish the corresponding amidated/imidated derivatives in good to excellent yields. Preliminary mechanistic and isotope-labeling studies suggest the reaction follows a radical pathway and involves an iminium ion intermediate.
authors.affiliation: Department of Chemistry, Indian Institute of Technology , New Delhi 110016, India.
authors.forename: Shailendra K
authors.initials: SK
authors.lastname: Singh
authors.affiliation: Department of Chemistry, Indian Institute of Technology , New Delhi 110016, India.
authors.forename: Nisha
authors.initials: N
authors.lastname: Chandna
authors.affiliation: Department of Chemistry, Indian Institute of Technology , New Delhi 110016, India.
authors.forename: Nidhi
authors.identifier: 0000-0001-8645-430X
authors.initials: N
authors.lastname: Jain