Heterocyclic Organotin Reagents for Stille Coupling

By: Aaron Thornton, Chemfiles Volume 11 Article 1

Stille reactions remain one of the most viable methods for the formation of C–C bonds in organic chemistry.1 Their use has been highlighted in various areas, including countless natural product syntheses, material science applications, and in numerous synthetic methodology studies. The coupling of imidazolyl stannane 718793 with heterocycle (4) by process chemists at Pfizer was reported in 2003 (Scheme 1).2 This coupling employed Pd(PPh3)4 as the catalyst and was carried out in 67% isolated yield. Addition/elimination on the resulting functionalized thienopyridine provided bulk material of the desired VEGFR kinase inhibitor (5). It is worth noting that of several cross-couplings which were examined, the Stille coupling employing stannane 718793 was the only reaction feasible on scales >50g.

Scheme 1: Stille reaction in the preparation of VEGFR kinase inhibitors (5).(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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