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Chemistry LibreTexts

15.17 Using Coupling Reactions to Alkylate Benzene

There are many other examples of coupling reactions in organic synthesis. The Suzuki reaction is somewhat similar to the Negishi reaction.

 

Figure 1.  The Suzuki reaction.

 

Reviews

Transmetallation

Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461–470.

Carrow, B.P.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 2116–2119.

Reductive Elimination

Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.

Conditions

 

Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437–3440.
Miyaura, N.; Suzuki, A. J. Chem. Soc., Chem. Commun. 1979, 866–867.
Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513–519.
Miyaura, N.; Yano, T.; Suzuki, A. Tetrahedron Lett. 1980, 21, 2865–2868.

Catalysts and Ligands

Goodson, F. E.; Wallow, T. I.; Novak, B. M. Org. Synth. 1997, 75, 61–68.

Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804-3805.