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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.
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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.
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 ...
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