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 crosscoupling was illustrated by the gram-scale synthesis of a patented thermally activated delayed fluorescence emitter for organic lightemitting diodes.
A practical nickel-catalyzed C−N cross-coupling reaction between diarylamines and aryl halides has been developed using commercially available NiCl 2 (dppf) as the catalyst. This robust method can be efficiently applied to a variety of diarylamines which are privileged motifs in materials science, including phenoxazines, phenothiazines, carbazoles, diphenylamines, 9-10dihydroacridines, 10,11-dihydro-5H-dibenzo[b,f ]azepines, 5H-dibenzo[b,f ]azepines, and 9H-tribenzo[b,d,f ]azepines.
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