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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 Shapiro reaction can also be combined with the Suzuki reaction to produce a variety of olefin products. Keay and coworkers have developed methodology that combines these reactions in a one pot process that does not require the isolation of the boronic acid, a setback of the traditional Suzuki coupling. This reaction has a wide scope ...
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]
Akira Suzuki (鈴木 章, Suzuki Akira, born September 12, 1930) is a Japanese chemist and Nobel Prize Laureate (2010), who first published the Suzuki reaction, the organic reaction of an aryl- or vinyl-boronic acid with an aryl- or vinyl-halide catalyzed by a palladium(0) complex, in 1979.
Pd-catalyzed decarboxylative cross-coupling of aryl halides with potassium cyanoacetate, reported by Yeung et al. Contrarily to Cu-only systems, decarboxylative palladation is the rate-limiting step in the palladium catalytic cycle. [4] Decarboxylative cross-coupling of potassium polyfluorobenzoates, reported by Shang et al.
Heck was awarded the 2010 Nobel Prize in Chemistry, which he shared with Ei-ichi Negishi and Akira Suzuki, for the discovery and development of this reaction. This reaction was the first example of a carbon-carbon bond-forming reaction that followed a Pd(0)/Pd(II) catalytic cycle, the same catalytic cycle that is seen in other Pd(0)-catalyzed ...
Nickel- and palladium-catalyzed couplings mainly focus on aryl-aryl couplings. Aryl-alkyl and especially alkyl-alkyl couplings are less successful because of β-hydride elimination can lower the yield. In Hydroformylation, β-hydride elimination can act as a side reaction that influences product regioselectivity. [4]
The coupling of a terminal alkyne and an aromatic ring is the pivotal reaction when talking about applications of the copper-promoted or copper-free Sonogashira reaction. The list of cases where the typical Sonogashira reaction using aryl halides has been employed is large, and choosing illustrative examples is difficult.