Suzuki cross-coupling reaction—a transition metal-catalyzed coupling reaction

One of the best-known cross-coupling reactions is the Suzuki or Suzuki-Miyaura reaction, where organoboron compounds and organic halides or triflates react in the presence of a palladium catalyst to form carbon-carbon bonds. First reported in 1979, this reaction offers several advantages over other cross-coupling reactions, particularly the Stille reaction, boronic acids being much less toxic and environmentally damaging than the organostannanes.

Like the Stille reaction, the Suzuki cross-coupling reaction is carried out under mild conditions, allowing reactions with a wide range of functional groups; and morover boronic acids are stable in aqueous conditions.

Since the discovery of this reaction, a great many boronic acids and esters have been synthesized, generating a broad selection of reactants with varying substituents. More recently, other boron-containing compounds such as trifluoroborates have been developed in place of the boronic acids.

The Suzuki cross-coupling methodology was used to synthesize the natural product epothilone A and the protease inhibitor TMC-95A.

Review available Thermo Scientific products for the Suzuki cross-coupling reaction:

View Suzuki Cross-Coupling Reaction video