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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.
The Heck reaction is the palladium-catalyzed coupling of an aryl or alkenyl halide with an alkene to form a substituted alkene. [2] Intramolecular variants of the reaction may be used to generate cyclic products containing endo or exo double bonds. Ring sizes produced by the intramolecular Heck reaction range from four to twenty-seven atoms.
The reaction is named after Ei-ichi Negishi who was a co-recipient of the 2010 Nobel Prize in Chemistry for the discovery and development of this reaction. Negishi and coworkers originally investigated the cross-coupling of organoaluminum reagents in 1976 initially employing Ni and Pd as the transition metal catalysts, but noted that Ni ...
The reaction of a substituted amide with phosphorus oxychloride gives a substituted chloroiminium ion (2), also called the Vilsmeier reagent. The initial product is an iminium ion (4b), which is hydrolyzed to the corresponding ketone or aldehyde during workup. [7] The Vilsmeier–Haack reaction
In one important reaction type, a main group organometallic compound of the type R-M (where R = organic group, M = main group centre metal atom) reacts with an organic halide of the type R'-X with formation of a new carbon-carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction. [1] [2] [3]
The alkynylation reaction of aryl halides using aromatic acetylenes was reported in 1975 in three independent contributions by Cassar, [4] Dieck and Heck [5] as well as Sonogashira, Tohda and Hagihara. [6] All of the reactions employ palladium catalysts to afford the same reaction products.
Palladium complexes containing chiral phosphinooxazolines are efficient catalysts for the Heck reaction. [14] [15] Pd-PHOX catalysts have also been used for intramolecular Heck reactions and examples exist where they have been shown to be superior to more common ligands such as BINAP.
English: Heck Reaction Wang 2000 Mechanism. Date: 20 December 2007 (original upload date) Source: Transferred from to Commons by Ronhjones using CommonsHelper.