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Intramolecular Heck reaction information


The intramolecular Heck reaction (IMHR) in chemistry is the coupling of an aryl or alkenyl halide with an alkene in the same molecule. The reaction may be used to produce carbocyclic or heterocyclic organic compounds with a variety of ring sizes. Chiral palladium complexes can be used to synthesize chiral intramolecular Heck reaction products in non-racemic form.[1]

  1. ^ Link, J. T. Org. React. 2002, 60, 157. doi:10.1002/0471264180.or060.02

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Intramolecular Heck reaction

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The intramolecular Heck reaction (IMHR) in chemistry is the coupling of an aryl or alkenyl halide with an alkene in the same molecule. The reaction may...

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Heck reaction

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The Heck reaction (also called the Mizoroki–Heck reaction) is the chemical reaction of an unsaturated halide (or triflate) with an alkene in the presence...

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Ugi reaction

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The Ugi reaction has been applied in combination with an intramolecular Diels-Alder reaction in an extended multistep reaction. A reaction in its own...

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Phosphinooxazolines

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greatly reduced. Pd-PHOX catalysts have also been used for intramolecular Heck reactions and examples exist where they have been shown to be superior...

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Cascade reaction

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not hold true. Although often composed solely of intramolecular transformations, cascade reactions can also occur intermolecularly, in which case they...

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Stille reaction

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Buchwald-Hartwig amination, another palladium-catalyzed coupling reaction, followed by an intramolecular Stille-Kelly coupling. Note that the aryl-iodide bond will...

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Galantamine total synthesis

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reaction using acetone cyanohydrine as the source of cyanide, to yield 10 followed by aldehyde deprotection to 11. The intramolecular Heck reaction to...

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Perfluorobutanesulfonyl fluoride

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of Bis(enolnonaflates) and their 4-exo-trig-Cyclizations by Intramolecular Heck Reactions". Synlett. 1999 (10): 1654–1656. doi:10.1055/s-1999-2892. ISSN 0936-5214...

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Kinetic isotope effect

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saccharose. Another reaction mechanism that was elucidated using the KIE is halogenation of toluene: In this particular "intramolecular KIE" study, a benzylic...

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Danishefsky Taxol total synthesis

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the terminal alkene 38 in a Wittig reaction involving methylenetriphenylphosphorane. The intramolecular Heck reaction involved tetrakis(triphenylphosphine)palladium(0)...

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Palladacycle

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in 1990s. Derivatives of tris(o-tolyl)phosphine proved effective in Heck reactions. There are two distinct types of palladacycle: four-electron donor (CY)...

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Dicobalt octacarbonyl

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complex itself can also be used in the Pauson–Khand reaction. Intramolecular Pauson–Khand reactions, where the starting material contains both the alkene...

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Alkene carboamination

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S. R. (2012). "Copper-catalyzed enantioselective intramolecular alkene amination/intermolecular heck-type coupling cascade". J. Am. Chem. Soc. 134 (4):...

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Organopalladium chemistry

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is reported by Malatesta and Angoletta. 1972 - The Heck reaction is a coupling reaction of a halogenide with an olefin. Pd(0) intermediates are implicated...

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Hiyama coupling

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this reaction (indicative of faster reactions). Heck reaction Kumada coupling Negishi coupling Sonogashira coupling Stille reaction Suzuki reaction Palladium-catalyzed...

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Carboboration

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and reagents utilized in the reaction. Shown below are examples of two types of Pd-catalyzed alkene 1,2 carboborations, Heck-type and the Wacker-type. However...

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Nucleophilic abstraction

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nucleophilic abstraction is the production of linear acyl derivatives. The intramolecular attack of these linear acyl derivatives gives rise to cyclic compounds...

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PEPPSI

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actively participate in the reaction mechanism since the pyridine group acts as an internal base to enable the intramolecular proton transfer between active...

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Bioconjugation

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azaylide through a four-membered ring transition state, and then an intramolecular reaction leads to the iminophosphorane intermediate, which will then give...

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Carbometalation

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elementary step of a reaction catalyzed by a palladium catalyst (Mizoroki-Heck reaction) and can also refer to a carbometalation reaction with a palladium...

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Protecting group

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ISBN 0-471-69754-0. J.M. McClure, Samuel J. Danishefsky: "A novel Heck arylation reaction: rapid access to congeners of FR 900482", in: J. Am. Chem. Soc...

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