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

Liqin Jiang, Xu Lu, Hui Zhang, 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

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

DOI: 10.1021/jo9006738

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Abstract

CuI/4-hydroxy-l-proline-catalyzed coupling of aryl bromides and N-Boc hydrazine takes place in DMSO to give N-aryl hydrazides. When aryl iodides are employed, no ligand is required. Under the catalysis of CuI/4-hydroxy-l-proline, the coupling reaction of aqueous ammonia with aryl bromides proceeds smoothly to afford primary arylamines.

see article for more examples

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Assembly of Primary (Hetero)Arylamines via CuI/Oxalic Diamide-Catalyzed Coupling of Aryl Chlorides and Ammonia

M. Fan, W. Zhou, Y. Jiang, D. Ma, Org. Lett., 2015, 17, 5934-5937.

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

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

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Key Words

Hydrazides, Anilines, Ullmann Reaction

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ID: J42-Y2009-1790