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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 solution-phase intermediates are not necessarily distinguishable from those obtained during homogeneous cross-couplings – for example, a heterogeneous Pd-catalyzed Suzuki reaction still proceeds via oxidative addition of the electrophile by Pd(0), transmetallation of a boronate, and reductive elimination to give product and regenerate Pd ...
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 ...
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 ...
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.
Cross-coupling reactions are important for the production of pharmaceuticals, [4] examples being montelukast, eletriptan, naproxen, varenicline, and resveratrol. [21] with Suzuki coupling being most widely used. [22] Some polymers and monomers are also prepared in this way. [23]
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The Suzuki-Miyaura and Negishi cross-coupling reactions were typically performed with Pd(PPh 3) 4 as catalyst and were mostly limited to aryl bromides and iodides at elevated temperatures, while the widely available aryl chlorides were unreactive. Dialkylbiaryl phosphine ligands are sometimes referred to as the "Buchwald ligands."