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Assembly of N,N-Disubstituted Hydrazines and 1-Aryl-1H-indazoles via Copper-Catalyzed Coupling Reactions

Xiaodong Xiong, Yongwen Jiang and Dawei Ma*

*State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Email: Madwmail.sioc.ac.cn

X. Xiong, Y. Jiang, D. Ma, Org. Lett., 2012, 14, 2552-2555.

DOI: 10.1021/ol300847v (free Supporting Information)


Abstract

CuI-catalyzed coupling of N-acyl-N′-substituted hydrazines with aryl iodides affords N-acyl-N′,N′-disubstituted hydrazines regioselectively. N-Acyl-N′-substituted hydrazines can also react with 2-bromoarylcarbonylic compounds in the presence of 4-hydroxy-L-proline as ligand to provide 1-aryl-1H-indazoles.

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CuI/4-Hydro-L-proline as a More Effective Catalytic System for Coupling of Aryl Bromides with N-Boc Hydrazine and Aqueous Ammonia

L. Jiang, X. Lu, H. Zhang, Y. Jiang, D. Ma, J. Org. Chem., 2009, 74, 4542-4546.


Key Words

Hydrazides, Indazoles


ID: J54-Y2012-1600