Palladium-catalyzed cross-coupling of organolead compounds with organostannanes

Abstract

The palladium-catalyzed cross-coupling of organolead triacetates with organostannanes has been accomplished in the presence of Pd₂(dba)₃·CHCl₃ (5 mol%) and NaOMe (5 equiv.) in MeOH–MeCN (1:1) under mild conditions.

References

1. J. K. Stille, Angew. Chem., Int. Ed. Engl., 1986, 25, 508–524; T. N. Mitchell, Synthesis, 1992, 803; V. Farina, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, New York, 1995, vol. 12, ch. 3, 4; V. Farina, Pure Appl. Chem., 1996, 68, 73.
2. J. T. Pinhey, Aust. J. Chem., 1991, 44, 1353; J. T. Pinhey, Pure Appl. Chem., 1996, 68, 819; S. Hashimoto, Y. Miyazaki, T. Shinoda and S. Ikegami, J. Chem. Soc., Chem. Commun., 1990, 1100.
3. Y. Matano and H. Suzuki, Bull. Chem. Soc. Jpn., 1996, 69, 2673.
4. R. C. Larock and C. A. Fellows, J. Am. Chem. Soc., 1982, 104, 1900; R. C. Larock, S. Varaprah, H. H. Lau and C. A. Fellows, J. Am. Chem. Soc., 1984, 106, 5274; E. C. Tayler and A. Mckillop, Acc. Chem. Res., 1970, 3, 338; R. C. Larock and H. Yang, Synlett, 1994, 748.
5. R. M. Moriarty and W. R. Epa, Tetrahedron Lett., 1992, 33, 4095; R. J. Hinkle, G. T. Poulter and P. J. Stang, J. Am. Chem. Soc., 1993, 115, 11 626; S.-K. Kang, H.-W. Lee, J.-S. Kim and S.-C. Choi, Tetrahedron Lett., 1996, 37, 3723; S.-K. Kang, H.-W. Lee, S.-B. Jang, T.-H. Kim and J.-S. Kim, Synth. Commun., 1996, 26, 4311.
6. J. Morgan and J. T. Pinhey, J. Chem. Soc., Perkin Trans. 1, 1990, 715.
7. The CuCl-catalyzed homocoupling of vinyl- aryl-lead diacetates was reported by Pinhey see J. Morgan, C. J. Parkinson and J. T. Pinhey, J. Chem. Soc., Perkin Trans. 1, 1994, 3361.
8. K. Kikukawa, H. Umekawa and T. Matsuda, J. Organomet. Chem., 1986, 311, C44; G. Stork and R. C. A. Isaacs, J. Am. Chem. Soc., 1990, 112, 7399; C. A. Busacca, J. Swestock, R. E. Johnson, T. R. Bailey, L. Musza and C. A. Rodger, J. Org. Chem., 1994, 59, 7553; V. Farina and M. A. Hossain, Tetrahedron Lett., 1996, 37, 6997.
9. The substituted lead(IV) triacetates undergo homocoupling in the presence of Pd₂(dba)₃·CHCl₃(5 mol%) in CHCl₃ at room temperature for 10 min. See, S.-K. Kang, U. Shivkumar, C. Ahn, S.-C. Choi and J.-S. Kim, Synth. Commun., 1997, 27, 1893.
10. p-Methoxyphenyllead triacetate 1b was easily prepared from anisole by treatment with lead tetraacetate. See R. P. Kozyrod and J. T. Pinhey, Org. Synth., 1984, 62, 24.
11. S. Pelter, M. Rowlands and G. Clements, Synthesis, 1987, 51.
12. R. H. Young, R. L. Martin, N. Chinh, C. Mallon and R. H. Kayser, Can. J. Chem., 1972, 50, 932.
13. L. J. Baldwin, S. Pakray, R. N. Castle and M. L. Lee, J. Heterocyclic Chem., 1985, 22, 1667.
14. L. C. Willemsens, D. de V. J. Spierenburg and J. Wolters, J. Organomet. Chem., 1972, 39, C61.
15. T. Sone, R. Yokoyama, Y. Okuyama and K. Sato, Bull. Chem. Soc. Jpn., 1986, 59, 83.
16. H. C. Bell, J. R. Kalman, J. T. Pinhey and S. Sternhell, Aust. J. Chem., 1979, 32, 1521.
17. A. Kasahara, T. Izumi and T. Ogihara, J. Heterocyclic Chem., 1989, 26, 597.
18. Recently, it was reported that the modification of ligands influences the efficiency of the metal–metal exchange: C. J. Parkinson, J. T. Pinhey and M. J. Stoermer, J. Chem. Soc., Perkin Trans. 1, 1992, 1911.
19. The oxidative addition of organostannanes to a palladium(0) complex is known: E. Shirakawa, H. Yoshida and T. Hiyama, Tetrahedron Lett., 1997, 38, 5177.