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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.
Intramolecular Heck reactions have been employed for the construction of complex natural products. An example is the late-stage, macrocyclic ring closure in the total synthesis of the cytotoxic natural product (–)-Mandelalide A. [19] In another example a fully intramolecular tandem Heck reaction is used in a synthesis of (–)-scopadulcic acid.
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 ...
Pd(PPh 3) 4 is widely used as a catalyst for palladium-catalyzed coupling reactions. [7] Prominent applications include the Heck reaction, Suzuki coupling, Stille coupling, Sonogashira coupling, and Negishi coupling. These processes begin with two successive ligand dissociations followed by the oxidative addition of an aryl halide to the Pd(0 ...
In many of these catalytic cycles, reductive elimination is the product forming step and regenerates the catalyst; however, in the Heck reaction [17] and Wacker process, [18] reductive elimination is involved only in catalyst regeneration, as the products in these reactions are formed via β–hydride elimination.
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