27th International symposium: Synthesis in organic chemistry

Palladium-catalyzed highly regioselective monoarylation of arylhydrazines with aryl tosylates Yange Huang 1,2 , Pui Ying Choy 1,2 , Junya Wang 2 and Fuk Yee Kwong* 1,2 1 State Key Laboratory of Synthetic Chemistry and Department of Chemistry, The Chinese University of Hong Kong, China, 2 Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules, Shenzhen Research Institute of The Chinese University of Hong Kong, China A palladium-catalyzed C–N bond coupling reaction between arylhydrazines and aryl tosylates for facile synthesis of unsymmetrical N,N -diarylhydrazines has been developed. Employing the catalyst system of Pd(TFA) 2 associated with the newly developed phosphine ligand L1 , the monoarylation of arylhydrazine proceeds smoothly to afford desired products in good-to-excellent yields (up to 95%) with good functional group compatibility. This method provides an alternative synthetic pathway for accessing structurally diversified N,N -diarylhydrazines from simple and easily accessible coupling components. References 1. Y. Huang, P. Y. Choy, J. Wang, M. K. Tse, R. W.-Y Sun, A. S. C. Chan and F. Y. Kwong, J. Org. Chem., 2020, 85 , 14664- 14673. 2. C. M. So, Z. Zhou, C. P. Lau and F. Y. Kwong, Angew. Chem. Int. Ed. , 2008, 47 , 6402–6406. 3. M. H. Tse, P. Y. Choy and F. Y. Kwong, Acc. Chem. Res. , 2022, 55 , 3688-3705.

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