Heck reaction

The Heck reaction has become one of the most widely used catalytic carbon-carbon bond forming tools in organic synthesis. The Heck reaction is a palladium-catalyzed C-C coupling between aryl halides or vinyl halides and activated alkenes in the presence of a base.

 

Mechanism:

Literature:

Acylation, methylation, and carboxyalkylation of olefins by Group VIII metal derivatives. Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518- 5526.

Arylation of olefin with aryl iodide catalyzed by palladium. Mizoroki, T., Mori, K., Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.

Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides.  Heck, R. F., Nolley, J. P., Jr. J. Org. Chem., 1972, 37, 2320-2322.

Organophosphinepalladium complexes as catalysts for vinylic hydrogen substitution reactions. Dieck, H. A., Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133-1136.

Reviews:

Recent Developments and New Perspectives in the Heck Reaction. Cabri, W., Candiani, I. Acc. Chem. Res. 1995, 28, 2-7.

The Heck Reaction as a Sharpening Stone of Palladium Catalysis. I. P. Beletskaya, A. V. Cheprakov 1995, 28, 2-7.