A synthetic approach to N -aryl carbamates via copper-catalyzed Chan-Lam coupling at room temperature

Soo Yeon Moon, U. Bin Kim, Dan Bi Sung, Won Suk Kim

Research output: Contribution to journalArticlepeer-review

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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.

Original languageEnglish
Pages (from-to)1856-1865
Number of pages10
JournalJournal of Organic Chemistry
Volume80
Issue number3
DOIs
StatePublished - 6 Feb 2015

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