Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas
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Buchwald_Palladium-catalyzed cross.pdf
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Author(s)
Fors, Brett P.
Vinogradova, Ekaterina Viktor
Buchwald, Stephen Leffler
Date Issued
June 2012
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Vinogradova, Ekaterina V., Brett P. Fors, and Stephen L. Buchwald. “Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas.” Journal of the American Chemical Society 134, no. 27 (July 11, 2012): 11132-11135.
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Author's final manuscript
Abstract
An efficient method for palladium-catalyzed cross-coupling of aryl chlorides and triflates with sodium cyanate is reported. The protocol allows for the synthesis of unsymmetrical N,N′-di- and N,N,N′-trisubstituted ureas in one pot and is tolerant of a wide range of functional groups. Insight into the mechanism of aryl isocyanate formation was gleaned through studies of the transmetalation and reductive elimination steps of the reaction, including the first demonstration of reductive elimination from an arylpalladium isocyanate complex to produce an aryl isocyanate.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja305212v
