Stille Coupling

M. Kosugi et al., Chem. Letters 1977, 301 (1977); D. Milstein, J. K. Stille, J. Am. Chem. Soc. 100, 3636 (1978).

Palladium-catalyzed cross coupling reaction of organostannanes with organic halides, acetates or perfluorinated sulfonates lacking a sp3-hybridized β-hydrogen:

Allylic acetates as substrates: L. Del Valle et al., J. Org. Chem. 55, 3019 (1990). Effect of additives: S. Gronowitz et al., J. Organometal. Chem. 460, 127 (1993); V. Farina et al., J. Org. Chem. 59, 5905 (1994). Synthesis of α-methylene lactones: R. M. Adlington et al., J. Chem. Soc. Perkin Trans. I 1994, 1697. Solid-phase synthesis of 1,4-benzodiazepines: M. J. Plunkett, J. A. Ellman, J. Am. Chem. Soc. 117, 3306 (1995). Reviews: J. K. Stille, Angew. Chem. Int. Ed. 25, 508-524 (1986); M. Pereyre et al., Tin in Organic Synthesis (Butterworths, Boston, 1987) pp 185-207 passim. Review of synthetic applications: T. N. Mitchell, Synthesis 1992, 803-815. Cf. Heck Reaction; Suzuki Coupling.