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Heterocyclic Organotin Reagents for Stille Coupling

By: Josephine Nakhla, Chemfiles Volume 10 Article 3

Stille reactions remain one of the most viable methods for the formation of C–C bonds in organic chemistry. Their use has been highlighted in various areas, including countless elegant natural product syntheses, material science, and in synthetic methodology. The use of 1-Methyl-5- (tributylstannyl)imidazole (718793) by process chemists at Pfizer in a Stille reaction was reported in 2003. The coupling employed iodothienopyridine as the electrophile in the presence of Pd(PPh3)4 as the catalyst. Addition-elimination on the resulting functionalized thienopyridine provided bulk material of the desired VEGFR kinase inhibitor. It is worth noting that of several cross-couplings which were examined, the Stille coupling was the only reaction feasible on scales >50 g.

Scheme 1. Stille reaction in preparation of VEGFR kinase inhibitor

Scheme 1. Stille reaction in preparation of VEGFR kinase inhibitor (718793)

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  1. Mascitti, Vincent. Stille coupling. Name Reactions for Homologations (2009), (Pt. 1), 133–162.
  2. Ragan, J. A.; Raggon, J. W.; Hill, P. D.; Jones, B. P.; McDermott, R. E.; Munchhof, M. J.; Marx, M. A.; Casavant, J. M.; Cooper, B. A.; Doty, J. L.; Lu, Y. Org. Proc. Res. Dev. 2003, 7, 676.

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