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

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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… Click to show full abstract

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-C2-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.

Keywords: amide ligands; copper; cross coupling; oxalamide amide; synthesis; triarylamine synthesis

Journal Title: Organic letters
Year Published: 2022

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