Cu2+-based synthetic architectures have been well-studied to catalyze redox-neutral carbene transfer reactions between different diazo carbonyl compounds (carbene source) and heteroaryl coupling partners for N-H/O-H insertion reactions. Here, we report our current efforts to generate a water-tolerant catalyst for C—N bond-forming reactions in water and other low boiling solvents, representing an efficient protocol to obtain the desired products in good yields toward asymmetric hybrid-catalyst development. Outlined is our methodology toward the synthesis and characterization of a novel isoquinolinamine tridentate ligand system and the resulting Cu2+ complexes. These tridentate copper(II) complexes provide good conversion and highly substituted C–N product formation. This protocol provides an oxidant-free method and proceeds through milder reaction conditions and releasing environmentally benign N2, and sets the foundation for related enantioselective processes.

Assessment of aminoquinline-based tridentate (NNN)-Cu(II) catalysts towards the redox-neutral cross-coupling reaction of anilines with diazo carbonyl compounds

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