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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 ...
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 ...
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]
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 ...
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 ...
The Hiyama coupling is a palladium-catalyzed cross-coupling reaction of organosilanes with organic halides used in organic chemistry to form carbon–carbon bonds (C-C bonds). This reaction was discovered in 1988 by Tamejiro Hiyama and Yasuo Hatanaka as a method to form carbon-carbon bonds synthetically with chemo - and regioselectivity . [ 1 ]