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A Synthetic Approach to N-Aryl Carbamates via Copper-Catalyzed Chan-Lam Coupling at Room Temperature

Title
A Synthetic Approach to N-Aryl Carbamates via Copper-Catalyzed Chan-Lam Coupling at Room Temperature
Authors
Moon, Soo-YeonKim, U. BinSung, Dan-BiKim, Won-Suk
Ewha Authors
김원석
SCOPUS Author ID
김원석scopus
Issue Date
2015
Journal Title
JOURNAL OF ORGANIC CHEMISTRY
ISSN
0022-3263JCR Link
Citation
vol. 80, no. 3, pp. 1856 - 1865
Publisher
AMER CHEMICAL SOC
Indexed
SCI; SCIE; SCOPUS WOS
Abstract
A mild and efficient synthesis of N-arylcarbamates was achieved by reacting azidoformates with boronic acids in the presence of 10 mol % of copper chloride catalyst. The reaction proceeds readily in an open flask at room temperature without additional base, ligand, or additive. Rapid access to urea analogues via a two-step one-pot procedure is enabled by reacting N-arylcarbamates with aluminum-amine complexes. In addition, among several boronic acid derivatives prepared, dimethylphenyl boronate was found to react rapidly in its reaction with benzyl azidoformate, invoking in situ generation of this species in the catalytic cycle.
DOI
10.1021/jo502828r
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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