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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 ...
Mechanism of the Suzuki reaction. Both ionic and coordination palladium compounds are frequently used to catalyze cross-coupling reactions. The catalytic ability is due to palladium's ability to switch between the Pd 0 and Pd 2+ oxidation states. An organic compound adds across Pd 0 to form an organic Pd 2+ complex (oxidative addition).
Many mechanisms exist reflecting the myriad types of cross-couplings, including those that do not require metal catalysts. [7] Often, however, cross-coupling refers to a metal-catalyzed reaction of a nucleophilic partner with an electrophilic partner. Mechanism proposed for Kumada coupling (L = Ligand, Ar = Aryl).
A 2021 survey of heterogeneous metal catalyzed cross-couplings in the fine chemical industry reported, out of 22 examples, 19 Suzuki or Heck reactions, which included only 2 examples with N-basic heterocycles, and only 4 examples with a singly-ortho-substituted electrophile (representative example in Scheme 1). [1]
Among the cross-coupling reactions it follows in the number of publications right after Suzuki and Heck reaction [8] and a search for the term "Sonogashira" in SciFinder provides over 1500 references for journal publications between 2007 and 2010.
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