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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 Miyaura borylation has shown to work for: Alkyl halides, [ 2 ] aryl halides, [ 1 ] [ 3 ] [ 4 ] aryl halides using tetrahydroxydiboron , [ 5 ] aryl halides using bis-boronic acid, [ 6 ] aryl triflates , [ 7 ] aryl mesylates , [ 8 ] vinyl halides, [ 9 ] vinyl halides of α,β-unsaturated carbonyl compounds, [ 10 ] and vinyl triflates.
Then A. Suzuki and co-workers extend this kind of reaction to other organoboron compounds and other alkenyl, aryl, alkyl halides and triflate. The palladium-catalyzed cross-coupling reaction organoboron compounds and these organic halides to form carbon-carbon bonds are known as Suzuki–Miyaura cross-coupling. [41] [42] Suzuki-Miyaura Cross ...
The mechanism of organotrifluoroborate-based Suzuki-Miyaura coupling reactions has recently been investigated in detail. The organotrifluoroborate hydrolyses to the corresponding boronic acid in situ, so a boronic acid can be used in place of an organotrifluoroborate, as long as it is added slowly and carefully. [7] [8]
Protodeboronation is a well-known undesired side reaction, and frequently associated with metal-catalysed coupling reactions that utilise boronic acids (see Suzuki reaction). [1] For a given boronic acid, the propensity to undergo protodeboronation is highly variable and dependent on various factors, such as the reaction conditions employed and ...
Norio Miyaura (宮浦憲夫, Miyaura Norio) was a Japanese organic chemist. He was a professor of graduate chemical engineering at Hokkaido University. [1] His major accomplishments surrounded his work in cross-coupling reactions / conjugate addition reactions of organoboronic acids (for C-C bond-forming reactions) and addition / coupling reactions of diborons and boranes (to synthesize ...
Due to longstanding pushback and controversial health studies surrounding the ingredient, many processed food manufacturers have already shifted away from using Red Dye No. 3, opting instead for ...
The general mechanism for the Suzuki reaction. Pincer complexes have been shown to catalyse Suzuki-Miyaura coupling reactions, a versatile carbon-carbon bond forming reaction. Typical Suzuki coupling employ Pd(0) catalysts with monodentate tertiary phosphine ligands (e.g. Pd(PPh 3) 4). It is a very selective method to couple aryl substituents ...