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 (free Supporting Information)
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
M. Fan, W. Zhou, Y. Jiang, D. Ma, Org. Lett., 2015, 17, 5934-5937.
X. Xiong, Y. Jiang, D. Ma, Org. Lett., 2012, 14, 2552-2555.