Oxalamide/Amide Ligands: Enhanced and Copper-Catalyzed C-N Cross-Coupling for Triarylamine Synthesis

Triarylamines are privileged core structures that are found in versatile optoelectronic materials. New methods are constantly being sought for their preparation. Herein, a new protocol for triarylamine synthesis is presented where a wide range of diarylamines couple smoothly with aryl bromides mediated by a copper oxalamide (or amide) catalytic system. Notably, a new non C-2-symmetric 1-isoquinolinamide-based N,N-/N,O-bidentate ligand was introduced that could tolerate bulky diarylamines. Plenty of known optoelectronic functional molecules could be synthesized in good to excellent yields. The practicality of this C-N cross coupling was illustrated by the gram-scale synthesis of a patented thermally activated delayed fluorescence emitter for organic light emitting diodes.