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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 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.
Suzuki-Miyaura Cross-Coupling. In 2013, Joachim Podlech and co-workers determined the structure of Alternaria mycotoxin altenuic acid III by NMR spectroscopic analysis and completed its total synthesis. In the synthetic strategy, Suzuki-Miyaura Cross-Coupling reaction was used with a highly functionalized boronate and butenolides to synthesize ...
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 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."
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]
The most common type of coupling reaction is the cross coupling reaction. [1] [2] [3] Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki were awarded the 2010 Nobel Prize in Chemistry for developing palladium-catalyzed cross coupling reactions. [4] [5] Broadly speaking, two types of coupling reactions are recognized:
Typically the electrophilic coupling partner (R-X) is an aryl halide, but triflates are also used. Nucleophilic coupling (R'-Y) partners are more diverse. In the Suzuki reaction, boronic esters and boronic acids serve as nucleophilic coupling partners. [1] Expanding the scope of coupling partners is a focus methods development in organic ...