Heck reaction

Heck reaction
Named after Richard F. Heck
Reaction type Coupling reaction
Identifiers
Organic Chemistry Portal heck-reaction
RSC ontology ID RXNO:0000024

The Heck reaction (also called the Mizoroki–Heck reaction)[1] is the chemical reaction of an unsaturated halide (or triflate) with an alkene in the presence of a base and a palladium catalyst to form a substituted alkene. It is named after Tsutomu Mizoroki and Richard F. Heck. Heck was awarded the 2010 Nobel Prize in Chemistry, which he shared with Ei-ichi Negishi and Akira Suzuki, for the discovery and development of this reaction. This reaction was the first example of a carbon-carbon bond-forming reaction that followed a Pd(0)/Pd(II) catalytic cycle, the same catalytic cycle that is seen in other Pd(0)-catalyzed cross-coupling reactions. The Heck reaction is a way to substitute alkenes.[2][3][4][5]

The Heck reaction
The Heck reaction
The Heck reaction
  1. ^ Drahl, Carmen (May 17, 2010). "In Names, History And Legacy". Chem. Eng. News. 88 (22): 31–33. doi:10.1021/cen-v088n020.p031. Retrieved June 4, 2011.
  2. ^ Heck, R. F. (1982). "Palladium-catalyzed vinylation of organic halides". Org. React. 27: 345–390. doi:10.1002/0471264180.or027.02. ISBN 978-0471264187.
  3. ^ de Meijere, A.; Meyer, F. E. (1994). "Fine Feathers Make Fine Birds: The Heck Reaction in Modern Garb". Angew. Chem. Int. Ed. Engl. 33 (2324): 2379–2411. doi:10.1002/anie.199423791.
  4. ^ Beletskaya, I. P.; Cheprakov, A. V. (2000). "The Heck Reaction as a Sharpening Stone of Palladium Catalysis". Chem. Rev. 100 (8): 3009–3066. doi:10.1021/cr9903048. PMID 11749313.
  5. ^ Mc Cartney, Dennis; Guiry, Patrick J. (2011). "The asymmetric Heck and related reactions". Chem. Soc. Rev. 40 (10): 5122–5150. doi:10.1039/C1CS15101K. PMID 21677934.