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Furazan-containing bromoarenes in the Suzuki-Miyaura reaction

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Abstract

The palladium-catalyzed cross-coupling reactions of 3-[bromo(het)aryl]furazans and bromobenzofurazans with arylboronic acids afford target biaryls in good yields. 3-Bromo-4-phenylfurazan containing a bromine atom in the furazan ring undergoes decomposition under the reaction conditions.

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References

  1. G. C. Tron, F. Pagliai, E. D. Grosso, A. A. Genazzani, G. Sorba, J. Med. Chem., 2005, 48, 3260.

    Article  CAS  Google Scholar 

  2. Pat. US 6136821, Appl. WO 98/18796 [Chem. Abstr., 1998, 128:321633].

  3. Pat. US 6258843, Appl. WO 97/32853 [Chem. Abstr., 1997, 127:293133].

  4. Pat. US 2002/0028831 [Chem. Abstr., 2002, 137:370106].

  5. R. M. Paton, in Comprehensive Heterocyclic Chemistry II, Eds A. R. Katritzky, C. W. Rees, E. F. V. Scriven, Pergamon: Oxford, New York, 1996, Vol. 4, p. 229

    Chapter  Google Scholar 

  6. A. B. Sheremetev, N. N. Makhova, W. Friedrichsen, Adv. Heterocycl. Chem., 2001, 78, 65

    Article  CAS  Google Scholar 

  7. G. Nikonov, S. Bobrov, in Comprehensive Heterocyclic Chemistry III, Eds A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor, Elsevier Science, Amsterdam, London, 2008, Vol. 5, p. 315.

    Chapter  Google Scholar 

  8. A. B. Sheremetev, N. S. Aleksandrova, E. V. Mantseva, D. E. Dmitriev, Mendeleev Commun., 2000, 67

  9. A. B. Sheremetev, Yu. L. Shamshina, D. E. Dmitriev, D. V. Lyubetskii, M. Yu. Antipin, Heteroatom Chem., 2004, 15, 199

    Article  CAS  Google Scholar 

  10. A. B. Sheremetev, N. S. Aleksandrova, D. E. Dmitriev, Mendeleev Commun., 2006, 163.

  11. A. B. Sheremetev, V. O. Kulagina, I. L. Yudin, N. E. Kuzmina, Mendeleev Commun., 2001, 112

  12. A. B. Sheremetev, N. S. Aleksandrova, E. V. Mantseva, D. E. Dmitriev, Khim. Geterotsikl. Soedin., 2003, 1541 [Chem. Heterocycl. Compounds. (Engl. Transl.), 2003, 39, 1357].

    Google Scholar 

  13. A. B. Sheremetev, Yu. L. Shamshina, Izv. Akad. Nauk, Ser. Khim., 2004, 1079 [Russ. Chem. Bull., Int. Ed., 2004, 53, 1124].

  14. W. L. Driessen, P. L. A. Everstijin, Z. Naturforsch., 1978, 33B, 1120

    CAS  Google Scholar 

  15. A. D. Garnovskii, I. S. Vasil’chenko, S. G. Kochin, V. G. Zaletov, L. I. Khmelńitskii, K. M. Indrichan, Koord. Khim., 1988, 14, 900 [Sov. J. Coord. Chem. (Engl. Transl.), 1988, 14]

    CAS  Google Scholar 

  16. Koord. Khim., 1989, 15, 258 [Sov. J. Coord. Chem. (Engl. Transl.), 1989, 15]

  17. C. E. Stoner, A. L. Rheingold, T. B. Brill, Inorg. Chem., 1991, 30, 360

    Article  CAS  Google Scholar 

  18. C. Richardson, P. J. Steel, D.M. D’Alessandro, P. C. Junk, F. R. Keene, J. Chem. Soc., Dalton Trans., 2002, 2775.

  19. A. E. Vasil’vitskii, A. B. Sheremetev, T. S. Novikova, L. I. Khmelńitskii, O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 2876 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1989, 38, 2640].

    Google Scholar 

  20. N. Miyaura, A. Suzuki, Chem. Rev., 1995, 95, 2457

    Article  CAS  Google Scholar 

  21. A. Suzuki. in Metal-Catalyzed Cross-Coupling Reactions; Eds F. Diederich, P. J. Stang, Wiley-VCH, Weinheim, Germany, 1998, pp. 49–98

    Google Scholar 

  22. S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron, 2002, 58, 9633

    Article  CAS  Google Scholar 

  23. F. Alonso, I. P. Beletskaya, M. Yus, Tetrahedron, 2008, 64, 3047.

    Article  CAS  Google Scholar 

  24. Pat. WO 2004/087684 [Chem. Abstr., 2004, 141, 350175]

  25. Pat. US 2005/0282818 [Chem. Abstr., 2006, 144:51590].

  26. Appl. WO 97/18208 [Chem. Abstr., 1997, 127, 50650]

  27. N. Blouin, A. Michaud, D. Gendron, S. Wakim, E. Blair, R. Neagu-Plesu, M. Belletéte, G. Durocher, Ye Tao, M. Leclerc, J. Am. Chem. Soc., 2008, 130, 732.

    Article  CAS  Google Scholar 

  28. Pat. WO 2006/035283 [Chem. Abstr., 2006, 144, 370098].

  29. P. Vachal, L. M. Toth, Tetrahedron Lett., 2004, 45, 7157.

    Article  CAS  Google Scholar 

  30. R. Calvino, A. Serafino, B. Ferrarotti, A. Gasco, A. Sanfilippo, Arch. Pharm., 1984, 317, 695.

    Article  CAS  Google Scholar 

  31. N. Miyaura, T. Yanagi, A. Suzuki. Synth. Commun., 1981, 11, 513

    Article  CAS  Google Scholar 

  32. B. I. Alo, A. Kandil, P. A. Patil, M. J. Sharp, M. A. Siddiqui, V. Snieckus, J. Org. Chem., 1991, 56, 3763

    Article  CAS  Google Scholar 

  33. S. I. Sviridov, A. A. Vasil’ev, N. L. Sergovskaya, M. V. Chirskaya, S. V. Shorshnev, Tetrahedron, 2006, 62, 2639.

    Article  CAS  Google Scholar 

  34. M. Milone, Gazz. Chim. Ital., 1932, 62, 432.

    CAS  Google Scholar 

  35. A. B. Sheremetev, Izv. Akad. Nauk, Ser. Khim., 2005, 1030 [Russ. Chem. Bull., Int. Ed., 2005, 53, 1057].

  36. M. J. Sharp, V. Snieckus, Tetrahedron Lett., 1985, 26, 5997

    Article  CAS  Google Scholar 

  37. J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc., 1999, 121, 9550

    Article  CAS  Google Scholar 

  38. M. Feuerstein, H. Doucet, M. Santelli, J. Organomet. Chem., 2003, 687, 327

    Article  CAS  Google Scholar 

  39. W. Su, S. Urgaonkar, P. A. McLaughlin, J. G. Verkade, J. Am. Chem. Soc., 2004, 126, 16433.

    Article  CAS  Google Scholar 

  40. A. B. Sheremetev, I. V. Ovchinnikov, Heteroatom Chem., 1997, 8, 7.

    Article  CAS  Google Scholar 

  41. N. T. S. Phan, M. Van der Sluys, C. W. Jones, Adv. Synth. Catal., 2006, 348, 609.

    Article  CAS  Google Scholar 

  42. G. W. Kabalka, V. Namboodiri, L. Wang. Chem. Commun., 2001, 775

  43. A. G. Kuznetsov, D. N. Korolev, N. A. Bumagin, Izv. Akad. Nauk, Ser. Khim., 2003, 1783 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1882]

    Google Scholar 

  44. M. Wang, L. Wang, Chinese J. Chem., 2008, 26, 1683.

    Article  CAS  Google Scholar 

  45. R. F. W. Bader, Atoms in Molecules. A Quantum Theory, Clarendron Press, Oxford, 1990.

    Google Scholar 

  46. E. Espinosa, E. Molins, C. Lecomte, Chem. Phys. Lett., 1998, 285, 170

    Article  CAS  Google Scholar 

  47. E. Espinosa, I. Alkorta, I. Rozas, J. Elguero, E. Molins, Chem. Phys. Lett., 2001, 336, 457.

    Article  CAS  Google Scholar 

  48. K. A. Lyssenko, M. Yu. Antipin, Izv. Akad. Nauk, Ser. Khim., 2006, 1 [Russ. Chem. Bull., Int. Ed., 2006, 55, 1]

  49. K. A. Lyssenko, Yu. V. Nelyubina, R. G. Kostyanovsky, M. Yu. Antipin, Chem. Phys. Chem., 2006, 7, 2453

    Article  CAS  Google Scholar 

  50. Yu. V. Nelyubina, I. V. Glukhov, M. Yu. Antipin, K. A. Lyssenko, Chem. Commun., 2010, 3469

  51. Yu. V. Nelyubina, M. Yu. Antipin, I. A. Cherepanov, K. A. Lyssenko, CrystEngComm, 2010, 12, 77.

    Article  CAS  Google Scholar 

  52. G. Ponzio, Gazz. Chim. Ital., 1928, 58, 329.

    CAS  Google Scholar 

  53. R. R. Holmes, R. P. Bayer, J. Am. Chem. Soc., 1960, 82, 3454.

    Article  CAS  Google Scholar 

  54. D. Dal Monte, E. Sandri, L. Di Nunno, S. Florio, P. E. Todesko, J. Chem. Soc. (B), 1971, 2209.

  55. G. Tappi, P. V. Forni, Ann. Chim., 1949, 39, 338.

    CAS  Google Scholar 

  56. P. B. Ghosh, B. J. Everitt, J. Med. Chem., 1974, 17, 203.

    Article  CAS  Google Scholar 

  57. W. Moje, J. Org. Chem., 1964, 29, 3772.

    Article  Google Scholar 

  58. G. M. Sheldrick, SHELXTL v. 5.10, Structure Determination Software Suit, Bruker AXS, Madison, Wisconsin, USA.

  59. N. K. Hansen, P. Koppens, Acta Crystallogr. A, 1978, 34, 909.

    Article  Google Scholar 

  60. T. S. Koritsansky, S. T. Howard, T. Richter, P. Macchi, A. Volkov, C. Gatti, P. R. Mallinson, L. J. Farrugia, Z. Su, N. K. Hansen, XD-A Computer Program Package for Multipole Refinement and Topological Analysis of Charge Densities from Diffraction Data, 2003.

  61. F. L. Hirshfeld, Acta. Crystallogr., 1976, 32, 239.

    Google Scholar 

  62. A. Stash, V. Tsirelson, WinXPRO — A Program for Calculation of the Crystal and Molecular Propeties Using the Model Electron Density, Moscow, 2001.

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Correspondence to A. A. Vasil’ev or A. B. Sheremetev.

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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2262–2269, November, 2011.

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Vasil’ev, A.A., Struchkova, M.I., Sheremetev, A.B. et al. Furazan-containing bromoarenes in the Suzuki-Miyaura reaction. Russ Chem Bull 60, 2306–2314 (2011). https://doi.org/10.1007/s11172-011-0353-y

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  • DOI: https://doi.org/10.1007/s11172-011-0353-y

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