Heck Reaction

R. F. Heck, J. P. Nolley, Jr., J. Org. Chem. 37, 2320 (1972).

Stereospecific palladium-catalyzed coupling of alkenes with organic halides or triflates lacking sp³-hybridized β-hydrogens:



Variation of reaction parameters in the context of the asymmetric synthesis of (+)-vernolepin: K. Ohrai et al., J. Am. Chem. Soc. 116, 11737 (1994). Review of intramolecular reactions: L. E. Overman, Pure Appl. Chem. 66, 1423-1430 (1994); S. E. Gibson et al., Contemp. Org. Syn. 3, 447-471 (1996); J. T. Link, L. E. Overman, Met.-Catal. Cross-Coupling React. 1998, 231-269. Reviews: R. F. Heck, Org. React. 27, 345-390 (1982); A. de Meijere, F. E. Meyer, Angew. Chem. Int. Ed. 33, 2379-2411 (1994); W. Cabri, I. Candiani, Accts. Chem. Res. 28, 2-7 (1995). Review of mechanism: G. T. Crisp, Chem. Soc. Rev. 27, 427-436 (1998); of enantioselective syntheses: M. Shibasaki, E. M. Vogl, J. Organometal. Chem. 576, 1-15 (1999); O. Loiseleur et al., ibid. 16-22; U. Iserloh, D. P. Curran, Chemtracts 12, 289-296 (1999). Cf. Stille Coupling; Suzuki Coupling.