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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 ...
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 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.
1 Mechanism. Toggle Mechanism subsection. 1.1 Catalysts. 1.2 Leaving groups. 2 Carbon–carbon cross-coupling. ... [21] with Suzuki coupling being most widely used. [22]
Nucleophilic alkylating agents can displace halide substituents on a carbon atom through the SN2 mechanism. With a catalyst, they also alkylate alkyl and aryl halides, as exemplified by Suzuki couplings. The Kumada coupling employs both a nucleophilic alkylation step subsequent to the oxidative addition of the aryl halide (L = Ligand, Ar = Aryl).
Ring expansions can allow access to larger systems that can be difficult to synthesize otherwise. [6] Rings can be expanded by attack of the ring onto an outside group already appended to the ring (a migration/insertion), opening of a bicycle to a single larger ring, or coupling a ring closing with an expansion. [1]
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. [1] [2] [3] [4]
Because it is commonly recrystallized from chloroform, the complex is often supplied as the adduct [Pd 2 (dba) 3 ·CHCl 3]. [1] The purity of samples can be variable. [3] In [Pd 2 (dba) 3], the pair of Pd atoms are separated by 320 pm but are tied together by dba units. [4] The Pd(0) centres are bound to the alkene parts of the dba ligands.