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Palladium-Catalyzed C-Phenylation of Methyl Acrylate with Triphenylbismuth Dicarboxylates

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Abstract

A new catalytic reaction of C-phenylation of methyl acrylate with bismuth derivatives Ph3Bi(O2CR)2 (R = H, Me, Et, Bu, CF3, Ph) or Ph3BiCl2 in a 3 : 1 ratio was studied. The reaction was performed in the presence of 4 mol % palladium compounds PdCl2, Pd(OAc)2, Pd2(dba)3, Pd(Ph3P)2Cl2, and PdLCl2 (L = dppm, dppe, dppp, dppb, dppf, binap, xantphos) at 50°C in CH3CN, DMF, THF, or CH2Cl2 and gave methyl cinnamate (yield up to 85% based on the starting bismuth compound), diphenyl (up to 138%), and benzene (up to 59%).

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REFERENCES

  1. Finet, J.-P., Ligand Coupling Reactions with Heteroatomic Compounds, Oxford: Pergamon, 1998.

    Google Scholar 

  2. Suzuki, H. and Matano, Y., Organobismuth Chemistry, New York: Elsevier, 2001.

    Google Scholar 

  3. Asano, R., Moritani, I., Fujiwara, Y., and Teranishi, S., Bull. Chem. Soc. Jpn., 1973, vol. 46, no.9, p. 2910.

    CAS  Google Scholar 

  4. Kawamura, T., Kikukawa, K., Takagi, M., and Matsuda, T., Bull. Chem. Soc. Jpn., 1977, vol. 50, no.8, p. 2021.

    CAS  Google Scholar 

  5. Gushchin, A.V., Moiseev, D.V., and Dodonov, V.A., Zh. Obshch. Khim., 2002, vol. 72, no.10, p. 1669.

    Google Scholar 

  6. Motano, Y., Yoshimune, M., Asuma, N., and Suzuki, H., J. Chem. Soc., Perkin Trans. 1, 1996, no. 16, p. 1971.

  7. Matoba, K., Motofusa, S., Cho, C.S., Ohe, K., and Uemura, S., J. Organomet. Chem., 1999, vol. 574, no.1, p. 3.

    Article  CAS  Google Scholar 

  8. Cho, C.S., Yoshimori, Y., and Uemura, S., Bull. Chem. Soc. Jpn., 1995, vol. 68, no.3, p. 950.

    CAS  Google Scholar 

  9. Barton, D.H.R., Ozbalik, N., and Ramest, M., Tetrahedron, 1988, vol. 44, no.18, p. 5661.

    Article  CAS  Google Scholar 

  10. Ohe, T., Tanaka, T., Kuroda, M., Cho, C.S., Ohe, K., and Uemura, S., Bull. Chem. Soc. Jpn., 1999, vol. 72, no.8, p. 1851.

    Article  CAS  Google Scholar 

  11. Gushchin, A.V., Moiseev, D.V., and Dodonov, V.A., Izv. Ross. Akad. Nauk, Ser. Khim., 2001, no. 7, p. 1230.

  12. Moiseev, D.V., Gushchin, A.V., Shavirin, A.S., Kursky, Y.A., and Dodonov, V.A., J. Organomet. Chem., 2003, vol. 667, nos.1–2, p. 176.

    Google Scholar 

  13. Leeuwen, P.W.N.M., Kamer, P.C.G., Reek, J.N.H., and Dierkes, P., Chem. Rev., 2000, vol. 100, no.8, p. 2741.

    Google Scholar 

  14. Rabinovich, I.B., Nistratov, V.P., Tel'noi, V.I., and Sheiman, M.S., Termodinamika metalloorganicheskikh soedinenii (Thermodynamics of Organometallic Compounds), Nizhni Novgorod: Nizhegor. Gos. Univ., 1996.

    Google Scholar 

  15. Milas, N. and Surgenor, D., J. Am. Chem. Soc., 1946, vol. 68, no.2, p. 205.

    Article  CAS  Google Scholar 

  16. Stephenson, T.A., Morehouse, S.M., Powell, A.R., Heffer, J.P., and Wilkinson, G., J. Chem. Soc., 1965, no. 6, p. 3632.

  17. Ukai, T., Kawazura, H., Ishii, Y., Bonnet, J.J., and Ibers, J.A., J. Organomet. Chem., 1974, vol. 65, no.2, p. 253.

    Article  CAS  Google Scholar 

  18. Itatani, H., Bailar, J.C., J. Am. Oil Chem. Soc., 1967, vol. 44, no.1, p. 147.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Lobachevsky Nizhni Novgorod State University, Nizhni Novgorod, Russia

    Yu. B. Malysheva, D. V. Moiseev, A. V. Gushchin & V. A. Dodonov

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  1. Yu. B. Malysheva
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  2. D. V. Moiseev
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  3. A. V. Gushchin
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  4. V. A. Dodonov
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__________

Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 11, 2005, pp. 1849–1853.

Original Russian Text Copyright © 2005 by Malysheva, Moiseev, Gushchin, Dodonov.

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Malysheva, Y.B., Moiseev, D.V., Gushchin, A.V. et al. Palladium-Catalyzed C-Phenylation of Methyl Acrylate with Triphenylbismuth Dicarboxylates. Russ J Gen Chem 75, 1766–1770 (2005). https://doi.org/10.1007/s11176-005-0507-4

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  • DOI: https://doi.org/10.1007/s11176-005-0507-4

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