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Palladium-Catalyzed Synthesis of N-Aryl Carbamates

Ekaterina V. Vinogradova, Nathaniel H. Park, Brett P. Fors and Stephen L. Buchwald*

*Massachusetts Institute of Technology, Department of Chemistry, Cambridge, Massachusetts 02139, United States, Email:

E. V. Vinogradova, N. H. Park, B. P. Fors, S. L. Buchwald, Org. Lett., 2013, 15, 1394-1397.

DOI: 10.1021/ol400369n

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An efficient synthesis of aryl carbamates - including major carbamate protecting groups - was achieved by introducing alcohols into the reaction of palladium-catalyzed cross-coupling of aryl chlorides and triflates with sodium cyanate. This methodology also provides direct access to S-thiocarbamates and diisocyanate precursors to polyurethane materials.

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Key Words

coupling, alcoholysis, Boc-protected amines, multicomponent reactions

ID: J54-Y2013-0710