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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]
In organic synthesis this reaction is often replaced by palladium coupling reactions such as the Heck reaction, the Hiyama coupling, and the Sonogashira coupling. In a variation of the Ullmann reaction, β-bromo styrene is reacted with imidazole in an ionic liquid such as 1-butyl-3-methylimidazolium tetrafluoroborate to give an N ...
Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important reaction type is this: R−M + R'−X → R−R' + MX (R, R' = organic fragments, usually aryl; M = main group center such as Li or MgX; X = halide) These reactions are used to form carbon–carbon bonds but ...
In organic chemistry, the Wurtz reaction, named after Charles Adolphe Wurtz, is a coupling reaction in which two alkyl halides are treated with sodium metal to form a higher alkane. 2 R−X + 2 Na → R−R + 2 NaX. The reaction is of little value except for intramolecular versions, such as 1,6-dibromohexane + 2 Na → cyclohexane + 2 NaBr.
The Glaser coupling is a type of coupling reaction. It is by far one of the oldest coupling reactions and is based on copper compounds like copper(I) chloride or copper(I) bromide and an additional oxidant like air. The base used in the original research paper is ammonia and the solvent is water or an alcohol.
Bogdanovic and Bolte identified the nature and mode of action of the active species in some classical McMurry systems, [5] and an overview of proposed reaction mechanisms has been published. [3] It is of note that titanium dioxide is not generally a product of the coupling reaction.
The Suzuki reaction or Suzuki coupling is an organic reaction that uses a palladium complex catalyst to cross-couple a boronic acid to an organohalide. [1] [2] [3] It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichi Negishi for their contribution to the discovery and development of noble metal catalysis in organic ...
The Chan–Lam coupling reaction, also known as the Chan–Evans–Lam coupling, is a cross-coupling reaction between an aryl boronic acid and an alcohol or an amine to form the corresponding secondary aryl amines or aryl ethers, respectively. [1] The Chan–Lam coupling is catalyzed by copper complexes. It can be conducted in air at room ...