Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Arylation of Styrene by Palladium Acetate-Phosphine Complexes

  • Published : 1997.02.20
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Abstract

When phenylation of styrene was carried out in the presence of Pd(OAc)2 and PPh3 in benzene, trans-stilbene was obtained in good yield (566%) with high selectivity (98%) under mild condition (55 ℃, 50 psi O2, 20 h). Since trans-stilbene could be produced not only from benzene but also from phenyl group of PPh3 by migration of its phenyl group to Pd, the competitiveness of benzene and the migratory aptitude of aryl group of triarylphosphine toward styrene has been investigated with various phosphines (PR3: P(p-C6H4CH3)3, P(p-C6H4OCH3)3, P(p-C6H4F)3, P(p-C6H4Cl)3, P(C6H5)3, P(C6H11)3, P(OC4H9n)3, P(CH2C6H5)3 and P(C6F5)3). The yield and selectivity toward trans-stilbene are increased as the basicity of the phosphines increases. The composition of arylated olefin from arylphosphine, in turn, increases as the electronegativity of the substituent on the aryl group of arylphosphines increases.

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References

  1. Acc. Chem. Res. v.2 Tsuji, J.
  2. J. Am. Chem. Soc. v.90 Heck, R. F.
  3. J. Am. Chem. Soc. v.90 Heck, R. F.
  4. J. Am. Chem. Soc. v.90 Heck, R. F.
  5. J. Am. Chem. Soc. v.90 Heck, R. F.
  6. Tetrahedron Lett. Moritani, I.;Fujiwara, Y.
  7. Tetrahedron v.24 Fujiwara, Y.;Moritani, I.;Matsuda, M.
  8. Tetrahedron Lett. Fujiwara, Y.;Moritani, I.;Matsuda, M.;Teranishi, S.
  9. J. Catalysis v.6 Stern, E. W.;Spector, M. L.;Leftin, M. P.
  10. J. Am. Chem. Soc. v.27 Shue, R. S.
  11. J. Chem. Soc., Chem. Commun. Shue, R. S.
  12. J. Catalysis v.26 Shue, R. S.
  13. J. Am. Chem. Soc. v.91 Fujiwara, Y.;Moritani, I.;Danno, S.;Asano, R.;Teranishi, S.
  14. J. Chem. Soc., Chem. Commun. Fuchita, Y.;Hiraki, K.;Kamogawa, Y.;Suenaga, M.
  15. Polyhedron v.10 Fuchita, Y.;Kawakami, M.;Shimoke, K.
  16. Inorg. Chim. Acta v.216 Fuchita, Y.;Takeda, Y.;Taga, M.
  17. Tetrahedron v.29 Yamane, T.;Kikukawa, K.;Takagi, M.;Matsuda, T.
  18. Chem. Rev. v.77 Tolmaan, C. A.
  19. J. Chem. Soc., Chem. Commun. Danno, S.
  20. Bull. Jpn. Chem. Soc. v.50 Kawamura, T.;Kikukawa, K.;Takagi, M.;Matsuda, T.
  21. J. Organomet. Chem. v.235 Kikukawa, K.;Matsuda, T.