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Chemistry of 1,2-diphospholide anions and 1,2-diphospholes

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Abstract

The main trends in the chemistry of 1,2-diphosphacyclopentadienes (1,2-diphospholes) and their derivatives 1,2-diphosphacyclopentadienide anions (1,2-diphospholide anions) were systematized, analyzed, and generalized. Methods for the generation of 1,2-diphospholide anions and their reactions with organic and organoelement electrophiles, as well as with transition metal complexes, were considered. Particular attention was paid to the cycloaddition reactions of 1-alkyl-1,2-diphospholes to obtain polycyclic chiral phosphines. A comparative analysis of the reactivity of 1,2-diphospholes and 1,2-diphospholide anions with respect to other representatives of phosphacyclopentadienes and phosphacyclopentadienide anions was carried out. The potential of application of 1,2-diphosphacyclopentadiene derivatives for the design of materials with magnetic, catalytic, and optical properties was shown.

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References

  1. I. A. Bezkishko, A. A. Zagidullin, V. A. Milyukov, O. G. Sinyashin, Russ. Chem. Rev., 2014, 83, 555.

    Article  CAS  Google Scholar 

  2. N. Maigrot, N. Avarvari, C. Charrier, F. Mathey, Angew. Chem., Int. Ed., 1995, 107, 623.

    Article  Google Scholar 

  3. V. Miluykov, A. Kataev, O. Sinyashin, P. Lönnecke, E. Hey-Hawkins, Organometallics, 2005, 24, 2233.

    Article  CAS  Google Scholar 

  4. V. A. Miluykov, A. V. Kataev, E. Hey-Hawkins, O. G. Sinyashin, Russ. Chem. Bull., 2007, 56, 304.

    Article  CAS  Google Scholar 

  5. I. Bezkishko, V. Miluykov, A. Kataev, D. Krivolapov, I. Litvinov, O. Sinyashin, E. Hey-Hawkins, J. Organomet. Chem., 2008, 693, 3318.

    Article  CAS  Google Scholar 

  6. I. Bezkishko, V. Miluykov, O. Sinyashin, E. Hey-Hawkins, Phosphorus, Sulfur, Silicon, Relat. Elem., 2011, 186, 657.

    Article  CAS  Google Scholar 

  7. L. Kochetkova, I. Bezkishko, V. Miluykov, O. Sinyashin, Phosphorus, Sulfur, Silicon, Relat. Elem., 2015, 190, 863.

    Article  CAS  Google Scholar 

  8. L. R. Kochetkova, I. A. Bezkishko, V. A. Miluykov, D. R. Islamov, D. B. Krivolapov, O. N. Kataeva, O. G. Sinyashin, Russ. Chem. Bull., 2015, 64, 1912.

    Article  CAS  Google Scholar 

  9. V. A. Miluykov, L. R. Shakirova, I. A. Bezkishko, D. B. Krivolapov, O. G. Sinyashin, Russ. Chem. Bull., 2012, 61, 1483.

    Article  CAS  Google Scholar 

  10. L. S. H. Dixon, P. D. Matthews, S. A. Solomon, D. S. Wright, Eur. J. Inorg. Chem., 2015, 2041.

    Google Scholar 

  11. I. Jevtovikj, M. B. Sárosi, A. K. Adhikari, P. Lönnecke, E. Hey-Hawkins, Eur. J. Inorg. Chem., 2015, 2046.

    Google Scholar 

  12. L. S. H. Dixon, S. Hanf, J. E. Waters, A. D. Bond, D. S. Wright, Organometallics, 2018, 37, 4465.

    Article  CAS  Google Scholar 

  13. C. Charrier, H. Bonnard, G. Lauzon, F. Mathey, J. Am. Chem. Soc., 1983, 105, 6871.

    Article  CAS  Google Scholar 

  14. V. Caliman, P. Hitchcock, J. Nixon, J. Organomet. Chem., 1997, 536, 273.

    Article  Google Scholar 

  15. R. Battsch, P. Hitchcock, J. Nixon, J. Chem. Soc., Chem. Commun., 1989, 15, 1046.

    Article  Google Scholar 

  16. V. Miluykov, A. Kataev, O. Sinyashin, P. Lönnecke, E. Hey-Hawkins, Mendeleev Commun., 2006, 4, 204.

    Article  CAS  Google Scholar 

  17. Т. I. Burganov, S. A. Katsyuba, A. A. Zagidullin, E. E. Zvereva, V. A. Miluykov, O. G. Sinyashin, Russ. Chem. Bull., 2015, 64, 1896.

    Article  CAS  Google Scholar 

  18. V. A. Milyukov, I. A. Bezkishko, A. A. Zagidullin, O. G. Sinyashin, E. Hey-Hawkins, Russ. Chem. Bull., 2010, 59, 1232.

    Article  CAS  Google Scholar 

  19. A. Elvers, F. W. Heinemann, B. Wrackmeyer, U. Zenneck, Chem. Eur. J., 1999, 11, 3143.

    Article  Google Scholar 

  20. M. Hofmann, T. Clark, F. W. Heinemann, U. Zenneck, Eur. J. Inorg. Chem., 2008, 13, 2225.

    Article  CAS  Google Scholar 

  21. V. Miluykov, I. Bezkishko, A. Zagidullin, O. Sinyashin, P. Lönnecke, E. Hey-Hawkins, Eur. J. Org. Chem., 2009, 1269.

    Google Scholar 

  22. S. A. Katsyuba, T. I. Burganov, E. E. Zvereva, A. A. Zagidullin, V. A. Milyukov, P. Lönnecke, E. Hey-Hawkins, O. G. Sinyashin, J. Phys. Chem. A, 2014, 118, 12168.

    Article  CAS  PubMed  Google Scholar 

  23. A. Ionkin, W. Marshall, B. Fish, M. Schiffhauer, F. Davidson, C. McEwen, D. Keys, Organometallics, 2007, 26, 5050.

    Article  CAS  Google Scholar 

  24. P. Coggon, J. Engel, F. McPhail, L. Quin, J. Am. Chem. Soc., 1970. 92, 5779.

    Article  CAS  Google Scholar 

  25. D. Josa, A. Peña-Gallego, J. Rodríguez-Otero, E. Cabaleiro-Lago, J. Mol. Model., 2011, 17, 1267.

    Article  CAS  PubMed  Google Scholar 

  26. N. Martin, J. Robinson, J. Mol. Graph. Model., 2012, 38, 26.

    Article  CAS  PubMed  Google Scholar 

  27. T. I. Burganov, A. A. Zagidullin, S. A. Katsyuba, V. A. Miluykov, O. G. Sinyashin, Phosphorus, Sulfur, Silicon, Relat. Elem., 2016, 191, 1646.

    Article  CAS  Google Scholar 

  28. E. Zvereva, S. Grimme, S. Katsyuba, T. Burganov, A. Zagidullin, V. Milyukov, O. Sinyashin, J. Phys. Chem. A, 2013, 117, 6827.

    Article  CAS  PubMed  Google Scholar 

  29. T. Burganov, A. Zagidullin, E. Oshchepkova, S. Katsyuba, V. Miluykov, O. Sinyashin, Phosphorus, Sulfur, Silicon, Relat. Elem., 2015, 190, 858.

    Article  CAS  Google Scholar 

  30. T. Burganov, S. Katsyuba, A. Zagidullin, E. Oshchepkova, V. Miluykov, A. Monari, X. Assfeld, Dyes Pigments., 2019, 164, 363.

    Article  CAS  Google Scholar 

  31. A. Zagidullin, V. Miluykov, D. Krivolapov, S. Kharlamov, Sh. Latypov, O. Sinyashin, P. Lönnecke, E. Hey-Hawkins, Eur. J. Org. Chem., 2011, 4910.

    Google Scholar 

  32. E. Mattmann, F. Mercier, L. Ricard, F. Mathey, J. Org. Chem., 2002, 67, 5422.

    Article  CAS  PubMed  Google Scholar 

  33. S. R. Gilbertson, D. G. Genov, A. L. Rheingold, Org. Lett., 2000, 2, 2885.

    Article  CAS  PubMed  Google Scholar 

  34. T. Faitg, J. Soulié, J. Lallemand, F. Mercier, F. Mathey, Tetrahedron, 2000, 56, 101.

    Article  CAS  Google Scholar 

  35. F. Mercier, F. Brebion, R. Dupont, F. Mathey, Tetrahedron: Asymmetry, 2003, 14, 3137.

    Article  CAS  Google Scholar 

  36. M. Zhi, Z. Gan, R. Ma, H. Cui, E.-Q. Li, Z. Duan, F. Mathey, Org. Lett., 2019, 21, 3210.

    Article  CAS  PubMed  Google Scholar 

  37. Z. Gan, M. Zhi, R. Han, E.-Q. Li, Z. Duan, F. Mathey, Org. Lett., 2019, 21, 2782.

    Article  CAS  PubMed  Google Scholar 

  38. H. Hudson, G. Keglevich, Phosphorus, Sulfur, Silicon, Relat. Elem., 2008, 183, 2256.

    Article  CAS  Google Scholar 

  39. M. P. Duffy, F. Mathey, J. Am. Chem. Soc., 2009, 131, 7534.

    Article  CAS  PubMed  Google Scholar 

  40. Y. Xiang Ng, F. Mathey, Angew. Chem., Int. Ed., 2013, 52, 14140.

    Article  CAS  Google Scholar 

  41. L. Quin, Curr. Org Chem., 2006, 10, 43.

    Article  CAS  Google Scholar 

  42. A. Zagidullin, I. Bezkishko, V. Miluykov, О. Sinyashin, Mendeleev Commun., 2013, 23, 117.

    Article  CAS  Google Scholar 

  43. A. Zagidullin, V. Miluykov, O. Sinyashin, P. Lönnecke, E. Hey-Hawkins, Heteroatom Chem., 2014, 25, 28.

    Article  CAS  Google Scholar 

  44. J. Steinbach, P. Binger, M. Regitz, Synthesis, 2003, 42, 2720.

    Google Scholar 

  45. H. Zurmuhlen, M. Regitz, J. Organomet. Chem., 1987, 332, C1.

    Article  Google Scholar 

  46. A. Zagidullin, Y. Ganushevich, V. Miluykov, D. Krivolapov, O. Kataeva, O. Sinyashin, E. Hey-Hawkins, Org. Biomol. Chem., 2012, 10, 5298.

    Article  CAS  PubMed  Google Scholar 

  47. E. Mattmann, D. Simonutti, L. Ricard, F. Mercier, F. Mathey, J. Org. Chem., 2001, 66, 755.

    Article  CAS  PubMed  Google Scholar 

  48. M. Westerhausen, B. Stein, M. Ossberger, H. Görls, J. Ruiz, H. Nöth, P. Mayer, ARKIVOC, 2007, 3, 46.

    Google Scholar 

  49. A. Zagidullin, V. Miluykov, E. Oschepkova, A. Tufatullin, O. Kataeva, O. Sinyashin, Beilstein J. Org. Chem., 2015, 11, 169.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  50. A. Zagidullin, Y. Ganushevich, V. Miluykov, O. Sinyashin, E. Hey-Hawkins, Phosphorus, Sulfur, Silicon, Relat. Elem., 2013, 188, 238.

    Article  CAS  Google Scholar 

  51. A. Zagidullin, V. Miluykov, F. Poyancev, Sh. Latypov, O. Sinyashin, P. Lönnecke, E. Hey-Hawkins, Eur. J. Org. Chem., 2015, 5326.

    Google Scholar 

  52. E. S. Oshchepkova, A. A. Zagidullin, V. A. Miluykov, O. G. Sinyashin, Phosphorus, Sulfur, Silicon, Relat. Elem., 2016, 191, 1530.

    Article  CAS  Google Scholar 

  53. A. A. Zagidullin, E. S. Oshchepkova, I. V. Chuchelkin, S. A. Kondrashova, V. A. Miluykov, Sh. K. Latypov, K. N. Gavrilov, E. Hey-Hawkins, Dalton Trans., 2019, 48, 4677.

    Article  CAS  PubMed  Google Scholar 

  54. A. Zagidullin, V. Miluykov, O. Sinyashin, E. Hey-Hawkins, Catalysis Today, 2017, 279, 142.

    Article  CAS  Google Scholar 

  55. A. Мarinetti, F. Мathey, J. Fischer, A. Мitschler, J. Am. Chem. Soc., 1982, 104, 4484.

    Article  Google Scholar 

  56. A. A. Zagidullin, Y. S. Ganushevich, A. G. Kafiatullina, V. A. Miluykov, O. G. Sinyashin, Russ. Chem. Bull., 2015, 64, 1986.

    Article  CAS  Google Scholar 

  57. K. Lammertsma, Top. Curr. Chem., 2003, 229, 95.

    Article  CAS  Google Scholar 

  58. V. Milyukov, A. Zagidullin, E. Hey-Hawkins, O. Sinyashin, Russ. J. Coord. Chem., 2010, 36, 891.

    Article  CAS  Google Scholar 

  59. A. Zagidullin, E. Oshchepkova, T. Burganov, V. Miluykov, S. Katsyuba, O. Sinyashin, P. Lönnecke, E. Hey-Hawkins, J. Organomet. Chem., 2018, 867, 125.

    Article  CAS  Google Scholar 

  60. S. K. Latypov, Y. S. Ganushevich, S. A. Kondrashova, S. V. Kharlamov, V. A. Milyukov, O. G. Sinyashin, Organometallics, 2018, 37, 2348.

    Article  CAS  Google Scholar 

  61. L. Weber, R. Kirchhoff, R. Boese, H.-G. Stammler, B. Neumann, Organometallics, 1993, 12, 731.

    Article  CAS  Google Scholar 

  62. L. Weber, O. Sommer, H.-G. Stammler, B. Neumann, Z. Anorg. Allg. Chem., 1996, 622, 543.

    Article  CAS  Google Scholar 

  63. I. Bezkishko, V. Miluykov, O. Sinyashin, P. Lönnecke, E. Hey-Hawkins, Phosphorus, Sulfur, Silicon, Relat. Elem., 2016, 191, 665.

    Article  CAS  Google Scholar 

  64. V. A. Miluykov, I. A. Bezkishko, O. G. Sinyashin, P. Lönnecke, E. Hey-Hawkins, Mendeleev Commun., 2010, 20, 195.

    Article  CAS  Google Scholar 

  65. F. H. Heinemann, M. Zeller, U. Zenneck, Organometallics, 2004, 23, 1689.

    Article  CAS  Google Scholar 

  66. F. W. Heinemann, H. Pritzkow, M. Zeller, U. Zenneck, Organometallics, 2000, 19, 4283.

    Article  CAS  Google Scholar 

  67. I. A. Bezkishko, L. R. Kochetkova, I. A. Tufatullin, V. A. Miluykov, O. N. Kataeva, O. G. Sinyashin, J. Struct. Chem., 2014, 55, 1474.

    Article  CAS  Google Scholar 

  68. V. Miluykov, I. Bezkishko, D. Krivolapov, O. Kataeva, O. Sinyashin, E. Hey-Hawkins, A. Parameswaran, Y. Krupskaya, V. Kataev, R. Klingeler, B. Büchner, Organometallics, 2010, 29, 1339.

    Article  CAS  Google Scholar 

  69. V. A. Miluykov, I. A. Bezkishko, L. R. Kochetkova, O. N. Kataeva, T. P. Gerasimova, S. A. Katsyuba, O. G. Sinyashin, P. Lönnecke, E. Hey-Hawkins, A. Parameswaran, Y. Krupskaya, V. Kataev, B. Büchner, Dalton Trans., 2015, 44, 10259.

    Article  CAS  PubMed  Google Scholar 

  70. E. W. Abel, C. Towers, J. Chem. Soc., Dalton Trans., 1979, 814.

    Google Scholar 

  71. E. W. Abel, N. Clark, C. Towers, J. Chem. Soc., Dalton Trans., 1979, 1552.

    Google Scholar 

  72. R. Zaripov, E. Vavilova, V. Miluykov, I. Bezkishko, O. Sinyashin, K. Salikhov, V. Kataev, B. Büchner, Phys. Rev. B, 2013, 88, 094418.

    Article  CAS  Google Scholar 

  73. Y. Krupskaya, R. Zaripov, E. Vavilova, V. Miluykov, I. Bezkishko, D. Krivolapov, O. Kataeva, O. Sinyashin, E. Hey-Hawkins, V. Voronkova, K. Salikhov, V. Kataev, B. Büchner, Phys. Rev. B, 2011, 84, 092402.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences,”, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    I. A. Bezkishko, A. A. Zagidullin & V. A. Milyukov

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  1. I. A. Bezkishko
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  2. A. A. Zagidullin
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  3. V. A. Milyukov
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Correspondence to A. A. Zagidullin.

Additional information

We are gratefully acknowledge to Prof. Dr. Evamarie Hey-Hawkins and Dr Peter Lönnecke (Leipzig University) for fruitful cooperation in this field and the German Academic Exchange Service (DAAD) for international collaboration support.

Based on the materials of the International Markovnikov Congress on Organic Chemistry (June 21—28, 2019, Moscow—Kazan, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0435–0448, March, 2020.

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Bezkishko, I.A., Zagidullin, A.A. & Milyukov, V.A. Chemistry of 1,2-diphospholide anions and 1,2-diphospholes. Russ Chem Bull 69, 435–448 (2020). https://doi.org/10.1007/s11172-020-2782-y

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  • DOI: https://doi.org/10.1007/s11172-020-2782-y

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