Organic Chemistry Portal



Stille Coupling Made Easier - The Synergic Effect of Copper(I) Salts and the Fluoride Ion

Simon P. H. Mee, Victor Lee, Jack E. Baldwin*

*The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford OX1 3QY, UK, Email:

S. P. H. Mee, V. Lee, J. E. Baldwin, Angew. Chem. Int. Ed., 2004, 43, 1132-1136.

DOI: 10.1002/anie.200352738


The PdCl2/PtBu3 catalytic system with copper(I) iodide and cesium fluoride in DMF is most effective for coupling aryl bromides, while Pd(PPh3)4 is optimal when coupling iodides and triflates. The combination of copper(I) iodide and cesium fluoride should allow the synthesis of sterically hindered systems and promotes electronically disfavored coupling reactions.

see article for more examples

proposed mechanism

Key Words

copper, cross-coupling, fluorides, Stille Coupling, biaryls, dienes, styrenes

ID: J06-Y2004-100