Organic Chemistry Portal



Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas

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

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

E. V. Vinogradova, B. P. Fors, S. L. Buchwald, J. Am. Chem. Soc., 2012, 134, 11132-11135.

DOI: 10.1021/ja305212v (free Supporting Information)


An efficient method for palladium-catalyzed cross-coupling of aryl chlorides and triflates with sodium cyanate allows 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.

see article for more examples


Pd2dba3 and the ligand were preheated in toluene at 120C for 3 minutes before the introduction to the reaction mixture.

Ekaterina Vinogradova, May 5, 2012

Key Words

Urea Derivatives (Arylation, Amination)

ID: J48-Y2012-2250