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: jack.baldwinchem.ox.ac.uk

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

DOI: 10.1002/anie.200352738

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Abstract

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

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Key Words

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

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ID: J06-Y2004-100