Suzuki reaction



The Suzuki reaction is the biphenyls. Several reviews have been published.[3][4][5]

The reaction also works with pseudohalides, such as halides, and also with boron-esters instead of boronic acids.

Relative reactivity: R2-I > R2-OTf > R2-Br >> R2-Cl

First published in 1979 by Akira Suzuki, the Suzuki reaction phosphine supporting groups.

In many publications this reaction also goes by the name Miyaura-Suzuki reaction. It is also often referred to as "Suzuki Coupling".

Reaction mechanism

The Reductive elimination of the desired product 9 restores the original palladium catalyst 1.

Oxidative addition

Oxidative addition proceeds with retention of cis-palladium complex, which rapidly isomerizes to the trans-complex.[8]

Reductive elimination

Using deuterium-labelling, Ridgeway et al. have shown the reductive elimination proceeds with retention of stereochemistry.[9]

Scope

With a novel ligand, a catalyst loading of up to 0.001 mol% has been reported [10]:

References

  1. ^ Miyaura, N. et al. Tetrahedron Lett. 1979, 3437.
  2. ^ Miyaura, N.; Suzuki, A. Chem. Commun. 1979, 866.
  3. ^ Suzuki, A. Pure Appl. Chem. 1991, 63, 419-422. (Review)
  4. ^ Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (Review, doi:10.1021/cr00039a007)
  5. ^ Suzuki, A. J. Organometallic Chem. 1999, 576, 147–168. (Review)
  6. ^ Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461–470. (doi:10.1021/jo971681s)
  7. ^ Stille, J. K.; Lau, K. S. Y. Acc. Chem. Res. 1977, 10, 434–442. (doi:10.1021/ar50120a002)
  8. ^ Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954–959.
  9. ^ Ridgway, B. H.; Woerpel, K. A. J. Org. Chem. 1998, 63, 458–460. (doi:10.1021/jo970803d)
  10. ^ Catalysts for Suzuki-Miyaura Coupling Processes: Scope and Studies of the Effect of Ligand Structure Timothy E. Barder, Shawn D. Walker, Joseph R. Martinelli, and Stephen L. Buchwald J. AM. CHEM. SOC. 2005, 127, 4685-4696 doi:10.1021/ja042491j

See also
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Suzuki_reaction". A list of authors is available in Wikipedia.