Suzuki reaction

Suzuki reaction
Named after Akira Suzuki
Reaction type Coupling reaction
Identifiers
Organic Chemistry Portal suzuki-coupling
RSC ontology ID RXNO:0000140

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 synthesis.[4] This reaction is sometimes telescoped with the related Miyaura borylation; the combination is the Suzuki–Miyaura reaction. It is widely used to synthesize polyolefins, styrenes, and substituted biphenyls.

The general scheme for the Suzuki reaction is shown below, where a carbon-carbon single bond is formed by coupling a halide (R1-X) with an organoboron species (R2-BY2) using a palladium catalyst and a base. The organoboron species is usually synthesized by hydroboration or carboboration, allowing for rapid generation of molecular complexity.

General scheme of Suzuki reaction

Several reviews have been published describing advancements and the development of the Suzuki reaction.[5][6][7]

  1. ^ Miyaura, Norio; Yamada, Kinji; Suzuki, Akira (1979). "A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides". Tetrahedron Letters. 20 (36): 3437–3440. doi:10.1016/S0040-4039(01)95429-2. hdl:2115/44006.
  2. ^ Miyaura, Norio; Suzuki, Akira (1979). "Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst". Chem. Comm. (19): 866–867. doi:10.1039/C39790000866.
  3. ^ Miyaura, Norio; Suzuki, Akira (1995). "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds". Chemical Reviews. 95 (7): 2457–2483. CiteSeerX 10.1.1.735.7660. doi:10.1021/cr00039a007. S2CID 53050782.
  4. ^ Nobelprize.org. "The Nobel Prize in Chemistry 2010". Nobel Prize Foundation. Retrieved 2013-10-25.
  5. ^ Suzuki, Akira (1991). "Synthetic Studies via the cross-coupling reaction of organoboron derivatives with organic halides". Pure Appl. Chem. 63 (3): 419–422. doi:10.1351/pac199163030419.
  6. ^ Miyaura, Norio; Suzuki, Akira (1979). "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds". Chemical Reviews. 95 (7): 2457–2483. CiteSeerX 10.1.1.735.7660. doi:10.1021/cr00039a007. S2CID 53050782.(Review)
  7. ^ Suzuki, Akira (1999). "Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998". Journal of Organometallic Chemistry. 576 (1–2): 147–168. doi:10.1016/S0022-328X(98)01055-9.