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Heck reaction

About: Heck reaction is a research topic. Over the lifetime, 5670 publications have been published within this topic receiving 165040 citations.


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Journal ArticleDOI
TL;DR: The coupling protocol for aryl halides with olefins can be considered as a milestone for the development and application of organometallic catalysis in organic synthesis and set the stage for numerous further applications.
Abstract: Palladium is known to a broad audience as a beautiful, but expensive jewellery metal. In addition, it is nowadays found in nearly every car as part of the automotive catalysts, where palladium is used to eliminate harmful emissions produced by internal combustion engines. On the other hand, and not known to the general public, is the essential role of palladium catalysts in contemporary organic chemistry, a topic which has now been recognized with the Nobel Prize for Chemistry 2010. Have a look at any recent issue of a chemical journal devoted to organic synthesis and you will discover the broad utility of palladium-based catalysts. Among these different palladium-catalyzed reactions, the so-called cross-coupling reactions have become very powerful methods for the creation of new C C bonds. In general, bond formation takes place here between less-reactive organic electrophiles, typically aryl halides, and different carbon nucleophiles with the help of palladium. Remember the situation 50 years ago, when palladium began to make its way into organic chemistry. At that time C C bond formation in organic synthesis was typically achieved by stoichiometric reactions of reactive nucleophiles with electrophiles or by pericyclic reactions. Ironically, however, oxidation catalysis was the start of today s carbon–carbon bond-forming methods: The oxidation of olefins to carbonyl compounds, specifically the synthesis of acetaldehyde from ethylene (Wacker process) by applying palladium(II) catalysts, was an important inspiration for further applications. Probably also for Richard Heck, who worked in the 1960s as an industrial chemist with Hercules Corporation. There, in the late 1960s, he developed several coupling reactions of arylmercury compounds in the presence of either stoichiometric or catalytic amounts of palladium(II). Some of this work was published in 1968 in a remarkable series of seven consecutive articles, with Heck as the sole author! Based on the reaction of phenylmercuric acetate and lithium tetrachloropalladate under an atmosphere of ethylene, which afforded styrene in 80% yield and 10% trans-stilbene, he described in 1972 a protocol for the coupling of iodobenzene with styrene, which today is known as the “Heck reaction”. A very similar reaction had already been published by Tsutomo Mizoroki in 1971. However, Mizoroki didn t follow up on the reaction and died too young from cancer. The coupling protocol for aryl halides with olefins can be considered as a milestone for the development and application of organometallic catalysis in organic synthesis and set the stage for numerous further applications. Hence, palladium-catalyzed coupling reactions were disclosed continuously during the 1970s (Scheme 1). One of the related reactions is the Sonogashira coupling of aryl halides with alkynes, typically in the presence of catalytic amounts of palladium and copper salts.

487 citations

Journal ArticleDOI
TL;DR: The application of palladacycles as catalysts for cross-coupling and similar reactions is reviewed in this article, where the advantages and limitations of palladiacycle catalysts are discussed.

451 citations

Journal ArticleDOI
TL;DR: In this paper, a summary of palladium-catalyzed cross-coupling reactions, with emphasis on the use of nucleophilic N-heterocyclic carbenes (NHC) as ancillary ligand, is presented.

426 citations

Journal ArticleDOI
TL;DR: In this article, it is established that new reactive anionic palladium(0) complexes species are formed in which palladium is ligated by either chloride ions or acetate ions.

425 citations


Network Information
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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202387
2022173
2021135
2020159
2019146
2018156