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

CuI/4-hydroxy-l-proline-catalyzed coupling of aryl bromides and N-Boc hydrazine takes place in DMSO at 80 °C to give N-aryl hydrazides. When aryl iodides are employed, this reaction completes at 50 °C and no ligand is required. Under the catalysis of CuI/4-hydroxy-l-proline, the coupling reaction of...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-06, Vol.74 (12), p.4542-4546
Main Authors: Jiang, Liqin, Lu, Xu, Zhang, Hui, Jiang, Yongwen, Ma, Dawei
Format: Article
Language:English
Subjects:
Ammonia - chemistry
Aniline Compounds - chemical synthesis
Bromobenzenes - chemistry
Catalysis
Chemistry
Copper - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic Compounds, 1-Ring - chemical synthesis
Hydrazines - chemistry
Hydroxyproline - chemistry
Iodides - chemistry
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
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Summary:CuI/4-hydroxy-l-proline-catalyzed coupling of aryl bromides and N-Boc hydrazine takes place in DMSO at 80 °C to give N-aryl hydrazides. When aryl iodides are employed, this reaction completes at 50 °C and no ligand is required. Under the catalysis of CuI/4-hydroxy-l-proline, the coupling reaction of aqueous ammonia with aryl bromides proceeds smoothly at 50 °C to afford primary arylamines. In this case K2CO3 is found as a better base than Cs2CO3. These processes allow assembly of N-aryl hydrazides and primary arylamines that bear a wide range of functional groups including hydroxyl, amine, trifluoromethyl, ester, nitro, and ketone.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9006738