View PDF Version
 
DOI: 10.1039/A900419J (Paper) Reference Section for: J. Chem. Soc., Dalton Trans., 1999, 773-780

Reductive coupling of halogenothiophenes and halogenothiazoles catalysed by PdII in a basic alcohol medium

(Note: The full text of this document is currently only available in the PDF Version )

Yang Xie, Geok Kheng Tan, Yaw Kai Yan, Jagadese J. Vittal, Siu Choon Ng and T. S. Andy Hor

Abstract

A catalytic reductive coupling method has been developed whereby 2- and 3-bromo- and 2-iodothiophenes, 2-bromothiazole and 2-bromofuran are converted into their corresponding bithiophene, bithiazole and bifuran derivatives. The use of a basic alcohol medium favours the reductive coupling pathway over the hydrodehalogenation pathway, which is generally more facile when other reducing agents are used. The catalytic mechanisms are discussed. The syntheses and characterization of the proposed intermediate complexes, trans-[PdBr(C4H3S-C)(PPh3)2] 1, trans-[PdI(C4H3S-C)(PPh3)2] 2 and trans-(N,P)-[{PdBr(µ-C3H2NS-C2,N)(PPh3)}2]·½CHCl3 3 support the proposed mechanism and the catalytic results. Single-crystal X-ray crystallographic structure determinations of 2 and 3 were carried out.

References

  1. B. Krische, J. Hellberg and C. Lilja, J. Chem. Soc., Chem. Commun., 1987, 1476 RSC; J. Tanguy, A. Pron, M. Zargoska and I. Kulszewicz-Bajer, Synth. Met., 1991, 45, 81 CAS; M. Zargoska, I. Kulszewicz-Bajer, A. Pron, I. Firlej, P. Bernier and M. Galtier, Synth. Met., 1991, 45, 385 CrossRef; J. Roncali, Chem. Rev., 1992, 92, 711; 1997, 97, 173 Search PubMed; S. C. Ng, H. S. O. Chan, H. H. Huang and R. S. H. Seow, J. Chem. Res., 1996, (S) 232; (M) 1285 Search PubMed; S. C. Ng, H. S. O. Chan and P. Miao, J. Mater. Sci. Lett., 1997, 16, 1170 Search PubMed; H. S. O. Chan, S. C. Ng, R. S. H. Seow and M. J. G. Moderscheim, J. Mater. Chem., 1992, 2, 1135 CrossRef CAS.
  2. R. Taylor, in Thiophene and Its Derivatives, ed. S. Gronowitz, Wiley, New York, 1985, vol. 44 (part 1), ch. 3 Search PubMed.
  3. J. W. Sease and L. Zechmeister, J. Am. Chem. Soc., 1947, 69, 270 CrossRef CAS.
  4. K. Tamao, S. Kodama, I. Nakajima and M. Kumada, Tetrahedron, 1982, 38, 3347 CrossRef CAS.
  5. M. F. Semmelhack, P. M. Helquist and L. D. Jones, J. Am. Chem. Soc., 1971, 93, 5908 CrossRef CAS.
  6. H. Wynberg and A. Logothetis, J. Am. Chem. Soc., 1956, 78, 1958 CrossRef CAS.
  7. L. Antolini, F. Goldoni, D. Iarossi, A. Mucci and L. Schenetti, J. Chem. Soc., Perkin Trans. 1, 1997, 1957 RSC.
  8. Y. Xie, S. C. Ng, T. S. A. Hor and H. S. O. Chan, J. Chem. Res. (S), 1996, 150 Search PubMed; Y. Xie, S. C. Ng, B. Wu, F. Xue, T. C. W. Mak and T. S. A. Hor, J. Organomet. Chem., 1997, 531, 175 CrossRef CAS; Y. Xie, B. M. Wu, F. Xue, S. C. Ng, T. C. W. Mak and T. S. A. Hor, Organometallics, 1998, 17, 3988 CrossRef CAS.
  9. H. Y. Lew and C. R. Noller, Org. Synth., 1963, Coll. Vol. 4, 545.
  10. R. Sornay, J. M. Meunier and P. Fournari, Bull. Soc. Chim. Fr., 1971, 990 CAS.
  11. A. E. Lipkin, J. Gen. Chem. USSR, 1963, 33, 188; S. Gronowitz and H.-O. Karlsson, Ark. Kemi, 1960, 17, 89 Search PubMed; K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, K. Kodama, I. Nakajima, A. Minato and M. Kumada, Bull. Chem. Soc. Jpn., 1976, 49, 1958 CAS; D. G. Morrell and J. K. Kochi, J. Am. Chem. Soc., 1959, 84, 1421.
  12. C. Amatore, A. Jutand and A. Suarez, J. Am. Chem. Soc., 1993, 115, 9531 CrossRef CAS.
  13. E. Negishi and F. Liu, in Metal-Catalyzed Cross-Coupling Reactions, eds. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 1, p. 34 Search PubMed.
  14. F. Ozawa, T. I. Son, S. Ebina, K. Osakada and A. Yamamoto, Bull. Chem. Soc. Jpn., 1981, 54, 1868 CAS; W. De Gaaf, J. Boersma, W. J. J. Smeets, A. L. Spek and G. van Koten, Organometallics, 1989, 8, 2907 CrossRef CAS; F. Ozawa, I. Takashi and A. Yamamoto, J. Am. Chem. Soc., 1980, 102, 6457 CrossRef CAS.
  15. F. Balegroune, P. Braunstein, T. M. G. Carneiro, D. Grandjean and D. Matt, J. Chem. Soc., Chem. Commun., 1989, 582 RSC; F. Balegroune, D. Grandjean, D. Lakkis and D. Matt, J. Chem. Soc., Chem. Commun., 1992, 1084 RSC; P. Braunstein, T. M. G. Carneiro, D. Matt, F. Balegroune and D. Grandjean, Organometallics, 1989, 8, 1737 CrossRef CAS.
  16. R. Sustmann, J. Lau and M. Zipp, Recl. Trav. Chim. Pays-Bas, 1986, 105, 356 CAS; R. Sustmann and J. Lau, Chem. Ber., 1986, 119, 2531 CAS.
  17. C. K. Johnson ORTEP, Report ORNL 5138, Oak Ridge National Laboratory, Oak Ridge, TN, 1976.
  18. N. A. Bailey and R. Mason, J. Chem. Soc. A, 1968, 2594 RSC.
  19. T. Debaerdemaeker, A. Kutoglu, G. Schmid and L. Weber, Acta Crystallogr., Sect. B, 1973, 29, 1283 CrossRef CAS.
  20. M. M. Olmstead, J. P. Farr and A. L. Balch, Inorg. Chim. Acta, 1981, 52, 47 CrossRef CAS.
  21. E. S. Raper, Coord. Chem. Rev., 1994, 129, 91 CrossRef CAS; H. G. Raubenheimer, F. Scott, S. Cronje, P. H. van Rooyen and K. Psotta, J. Chem. Soc., Dalton Trans., 1992, 1009 RSC; S. K. Hadjikakou, P. Aslanidis, P. Karagiannidis, D. Mentzafos and A. Terzis, Polyhedron, 1991, 10, 935 CrossRef CAS; Inorg. Chim. Acta, 1991, 186, 199 Search PubMed; L. P. Battaglia, A. B. Corradi, M. R. Cramarossa, I. M. Vezzosi and J. G. Giusti, Polyhedron, 1993, 12, 2235 Search PubMed; R. Castro, J. A. Garcia-Vazquez, J. Romero, A. Sousa, C. A. McAuliffe and R. Pritchard, Polyhedron, 1993, 12, 2241 CrossRef CAS.
  22. G. Boche, C. Hilf, K. Harms, M. Marsch and J. C. W. Lohrenz, Angew. Chem., Int. Ed. Engl., 1995, 34, 487 CAS.
  23. K. Nakatsu, K. Kinoshita, H. Kanda, K. Isobe, Y. Nakamura and S. Kawaguchi, Chem. Lett., 1980, 913 CAS.
  24. Y. Xie, S. C. Ng, T. C. W. Mak and T. S. A. Hor, unpublished results.
  25. T. J. Giordano, W. M. Butler and P. G. Rasmussen, Inorg. Chem., 1978, 17, 1917 CrossRef CAS.
  26. K. Osakada, Y. Ozawa and A. Yamamoto, J. Chem. Soc., Dalton Trans., 1991, 759 RSC.
  27. K. Isobe, E. Kai, Y. Nakamura, K. Nishimoto, T. Miwa, S. Kawaguchi, K. Kinoshita and K. Nakatsu, J. Am. Chem. Soc., 1980, 102, 2475 CrossRef CAS.
  28. L. Nygaard, E. Asmussen, J. H. Hoeg, R. C. Maheshwari, C. H. Nielsen, I. B. Petersen, J. Rastrup-Andersen and G. O. Soerensen, J. Mol. Struct., 1971, 8, 225 CrossRef CAS.
  29. R. F. Heck, in Palladium Reagents in Organic Syntheses, Academic Press, New York, 1985, ch. 1, p. 18 Search PubMed.
  30. T. Hayachi, M. Konishi, Y. Kobori, M. Kumada, T. Higuchi and K. Hirotsu, J. Am. Chem. Soc., 1984, 106, 158 CrossRef CAS.
  31. D. R. Coulson, Inorg. Synth., 1972, 13, 121.
  32. J. M. Brown and P. J. Guiry, Inorg. Chim. Acta, 1994, 220, 249 CrossRef CAS.
  33. M. F. Rettig and P. M. Maitlis, Inorg. Synth., 1977, 17, 134 CAS.
  34. J. R. Doyle, P. E. Slade and H. B. Jonassen, Inorg. Synth., 1960, 6, 218.
  35. G. Booth and J. Chatt, J. Chem. Soc., 1965, 3238 RSC.
  36. B. Corain, B. Longato, G. Favero, D. Ajò, G. Pilloni, U. Russo and F. R. Kreissl, Inorg. Chim. Acta, 1989, 157, 259 CrossRef CAS.
  37. M. Meier and F. Basolo, Inorg. Synth., 1990, 28, 104 CAS.
  38. G. J. Kubas, Inorg. Synth., 1979, 19, 90 CAS.
  39. T. N. Sorrell and P. S. Pearlman, J. Org. Chem., 1980, 45, 3449 CrossRef.
  40. E. Khor, S. C. Ng, H. C. Li and S. Chai, Heterocycles, 1991, 32, 1805 CAS.
  41. R. C. Larock and J. C. Bernhardt, J. Org. Chem., 1977, 42, 1680 CrossRef CAS.
  42. SMART & SAINT Software Reference Manuals, Version 4.0, Siemens Energy & Automation, Inc., Analytical Instrumentation, Madison, WI, 1996 Search PubMed.
  43. G. M. Sheldrick SADABS, a Software for Empirical Absorption Correction, University of Göttingen, 1996.
  44. SHELXTL Reference Manual, Version 5.03, Siemens Energy & Automation, Inc., Analytical Instrumentation, Madison, WI, 1996 Search PubMed.
  45. Y. LePage, J. Appl. Crystallogr., 1987, 20, 264 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.