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15.17 Using Coupling Reactions to Alkylate Benzene

  • Page ID
    16386
  • 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.