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Transition metal-promoted reactions of diarylphosphine oxides as a synthetic method for organophosphorus heterocyclic compounds

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Chemistry of Heterocyclic Compounds Aims and scope

The present work considers main achievements and modern trends in methods of synthesis of organophosphorus heterocyclic compounds through mainly radical phosphorylation of the C(sp2)–H bonds of unsaturated compounds catalyzed by metal salts and complexes. It also summarizes new ways of obtaining both phosphorous cycles (P-cycles) and heterocycles with another heteroatom (N, O, etc.) containing an external organophosphorus substituent. The most important and promising areas of recent years including the synthesis of 1-benzophospholes, arylphosphonates, phosphines, and phosphine oxides are highlighted. The reactions of phosphorylation/cyclization with acetylene, 2-isocyanobiphenyl, alkynoates, and olefins are analyzed. The assumed mechanisms and intermediates in the reactions of formation of the C–P bond are considered. New 1-benzophosphole oxides possessing photochromic, fluorescent, and some other optical properties are described. The work draws attention to the potential of this intensively developed direction of the organoelemental chemistry in last 5 years.

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References

  1. Phosphorus Chemistry II, Synthetic Methods; Montchamp, J.-L., Ed.; Springer: Cham, 2015.

  2. Organophosphorus Chemistry; Allen, D. W.; Loakes, D.; Tebby, J. C., Eds.; RCS Publishing: London, 2012, Vol. 41.

  3. Alexandre, F.-R.; Amador, A.; Bot, S.; Caillet, C.; Convard, T.; Jakubik, J.; Musiu, C.; Poddesu, B.; Vargiu, L.; Liuzzi, M.; Roland, A.; Seifer, M.; Standring, D.; Storer, R.; Dousson, C. B. J. Med. Chem. 2011, 54, 392.

    Article  CAS  PubMed  Google Scholar 

  4. Queffélec, C.; Petit, M.; Janvier, P.; Knight, D. A.; Bujoli, B. Chem. Rev. 2012, 112, 3777.

    Article  CAS  PubMed  Google Scholar 

  5. Corbridge, D. E. C. Phosphorus: Chemistry, Biochemistry and Technology; CRC Press: Boca Raton, 2013, 6th ed.

    Book  Google Scholar 

  6. McClure, C. K. Phosphorus in Organic Chemistry; Wiley-VCH: Weinhein, 2012.

    Google Scholar 

  7. Xu, Q.; Zhou, Y.-B.; Zhao, C.-Q.; Yin, S.-F.; Han, L.-B. Mini-Rev. Med. Chem. 2013, 13, 824.

    Article  CAS  PubMed  Google Scholar 

  8. Budnikova, Yu. H.; Sinyashin, O. G. Russ. Chem. Rev. 2015, 84, 917. [Usp. Khim. 2015, 84, 917.]

  9. Pan, X.-Q.; Wang, L.; Zou, J.-P.; Zhang, W. Chem. Commun. 2011, 7875.

  10. Zhang, C.; Li, Z.; Zhu, L.; Yu, L.; Wang, Z.; Li, C. J. Am. Chem. Soc. 2013, 135, 14082.

    Article  CAS  PubMed  Google Scholar 

  11. Chu, X.-Q.; Zi, Y.; Meng, H.; Xu, X.-P.; Ji, S.-J. Chem. Commun. 2014, 7642.

  12. Gao, Y.; Tang, G.; Zhao, Y. Phosphorus, Sulfur Silicon Relat. Elem. 2017, 192(6), 589.

    Article  CAS  Google Scholar 

  13. Li, Y.-M.; Sun, M.; Wang, H.-L.; Tian, Q.-P.; Yang, S.-D. Angew. Chem., Int. Ed. 2013, 52, 3972.

    Article  CAS  Google Scholar 

  14. Li, Y.-M.; Shen, Y.; Chang, K.-J.; Yang, S.-D. Tetrahedron 2014, 70, 1991.

    Article  CAS  Google Scholar 

  15. Zhang, B.; Daniliuc, C. G.; Studer, A. Org. Lett. 2014, 16, 250.

    Article  CAS  PubMed  Google Scholar 

  16. Stolar, M.; Baumgartner, T. Chem.–Asian J. 2014, 9, 1212.

    Article  CAS  PubMed  Google Scholar 

  17. Gilard, V.; Martino, R.; Malet-Martino, M.; Niemeyer U.; Pohl, J. J. Med. Chem. 1999, 42, 2542.

    Article  CAS  PubMed  Google Scholar 

  18. Mader, M. M.; Bartlett, P. A. Chem. Rev. 1997, 97, 1281.

    Article  CAS  PubMed  Google Scholar 

  19. Darrow, J. W.; Drueckhammer, D. G. J. Org. Chem. 1994, 59, 2976.

    Article  CAS  Google Scholar 

  20. Kumar, A.; Sharma, P.; Gurram, V. K.; Rane, N. Bioorg. Med. Chem. Lett. 2006, 16, 2484.

    Article  CAS  PubMed  Google Scholar 

  21. Matano, Y.; Saito, A.; Fukushima, T.; Tokudome, Y.; Suzuki, F.; Sakamaki, D.; Kaji, H.; Ito, A.; Tanaka, K.; Imahori, H. Angew. Chem., Int. Ed. 2011, 50, 8016.

    Article  CAS  Google Scholar 

  22. Fukazawa, A.; Yamaguchi, E.; Ito, E.; Yamada, H.; Wang, J.; Irle, S.; Yamaguchi, S. Organometallics 2011, 30, 3870.

    Article  CAS  Google Scholar 

  23. Ren, Y.; Baumgartner, T. J. Am. Chem. Soc. 2011, 133, 1328.

    Article  CAS  PubMed  Google Scholar 

  24. Tsuji, H.; Sato, K.; Sato, Y.; Nakamura, E. Chem.–Asian J. 2010, 5, 1294.

    CAS  PubMed  Google Scholar 

  25. Tsuji, H.; Sato, K.; Sato, Y.; Nakamura, E. J. Mater. Chem. 2009, 19, 3364.

    Article  CAS  Google Scholar 

  26. Fukazawa, A.; Ichihashi, Y.; Kosaka, Y.; Yamaguchi, S. Chem.–Asian J. 2009, 4, 1729.

    Article  CAS  PubMed  Google Scholar 

  27. Matano, Y.; Imahori, H. Org. Biomol. Chem. 2009, 7, 1258.

    Article  CAS  PubMed  Google Scholar 

  28. Crassous, J.; Réau, R. Dalton Trans. 2008, 6865.

  29. Ren Y.; Baumgartner, T. Dalton Trans. 2012, 41, 7792.

    Article  CAS  PubMed  Google Scholar 

  30. Unoh, Y.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2013, 52, 12975.

    Article  CAS  Google Scholar 

  31. Chen, Y.-R.; Duan, W.-L. J. Am. Chem. Soc. 2013, 135, 16754.

    Article  CAS  PubMed  Google Scholar 

  32. Ma, W.; Ackermann, L. Synthesis 2014, 2297.

  33. Zhang, P.; Gao, Y.; Zhang, L.; Li, Z.; Liu, Y.; Tang, G.; Zhao, Y. Adv. Synth. Catal. 2016, 358, 138.

    Article  CAS  Google Scholar 

  34. Ma, D.; Chen, W.; Hu, G.; Zhang, Y.; Gao, Y.; Yin, Y.; Zhao, Y. Green Chem. 2016, 18, 3522.

    Article  CAS  Google Scholar 

  35. Quint, V.; Morlet-Savary, F.; Lohier, J.-F.; Lalevée, J.; Gaumont, A.-C.; Lakhdar, S. J. Am. Chem. Soc. 2016, 138, 7436.

    Article  CAS  PubMed  Google Scholar 

  36. Khrizanforova, V. V.; Khrizanforov, M. N.; Gryaznova, T. V.; Budnikova, Y. H. Phosphorus, Sulfur Silicon Relat. Elem. 2016, 191, 1602.

    Article  CAS  Google Scholar 

  37. Budnikova, Y. H.; Gryaznova, T. V.; Grinenko, V. V.; Dudkina, Y. B.; Khrizanforov, M. N. Pure Appl. Chem. 2017, 89, 311.

    CAS  Google Scholar 

  38. Hu, G.; Zhang, Y.; Su, J.; Li, Z.; Gao, Y.; Zhao, Y. Org. Biomol. Chem. 2015, 13, 8221.

    Article  CAS  PubMed  Google Scholar 

  39. Wu, N. M.-W.; Wong, H.-L.; Yam, V. W.-W. Chem. Sci. 2017, 8, 1309.

    Article  CAS  PubMed  Google Scholar 

  40. Hay, C.; Fischmeister, C.; Hissler, M.; Toupet, L.; Réau, R. Angew. Chem., Int. Ed. 2000, 39, 1812.

    Article  CAS  Google Scholar 

  41. Bouit, P.-A.; Escande, A.; Szűcs, R.; Szieberth, D.; Lescop, C.; Nyulászi, L.; Hissler, M.; Réau, R. J. Am. Chem. Soc. 2012, 134, 6524.

    Article  CAS  PubMed  Google Scholar 

  42. Unoh, Y.; Yokoyama, Y.; Satoh, T.; Hirano, K.; Miura, M. Org. Lett. 2016, 18, 5436.

    Article  CAS  Google Scholar 

  43. Koyanagi, Y.; Kawaguchi, S.; Fujii, K.; Kimura, Y.; Sasamori, T.; Tokitoh, N.; Matano, Y. Dalton Trans. 2017, 9517

  44. Elaieb, F.; Hedhli, A.; Sémeril, D.; Matt, D.; Harrowfield, J. Eur. J. Org. Chem. 2016, 3103.

  45. Elaieb, F.; Sémeril, D.; Matt, D.; Pfeffer, M.; Bouit, P.-A.; Hissler, M.; Gourlaouen, C.; Harrowfield, J. Dalton Trans. 2017, 46, 9833.

    Article  CAS  PubMed  Google Scholar 

  46. Zhang, B.; Daniliuc, C. G.; Studer, A. Org. Lett. 2014, 16, 250.

    Article  CAS  PubMed  Google Scholar 

  47. Yang, B.; Tian, Q.; Yang, S. Chin. J. Org. Chem. 2014, 34, 717.

    Article  CAS  Google Scholar 

  48. Cao, J.-J.; Zhu, T.-H.; Gu, Z.-Y.; Hao, W.-J.; Wang, S.-Y.; Ji, S.-J. Tetrahedron 2014, 70, 6985.

    Article  CAS  Google Scholar 

  49. Li, Y.; Qiu, G.; Ding, Q.; Wu, J. Tetrahedron 2014, 70, 4652.

    Article  CAS  Google Scholar 

  50. Gao, Y.; Wu, J.; Xu, J.; Wang, X.; Tang, G.; Zhao, Y. Asian J. Org. Chem. 2014, 3, 691.

    Article  CAS  Google Scholar 

  51. Li, C.-X.; Tu, D.-S.; Yao, R.; Yan, H.; Lu, C.-S. Org. Lett. 2016, 18, 4928.

    Article  CAS  PubMed  Google Scholar 

  52. Abdel-Halim, O. B.; Morikawa, T.; Ando, S.; Matsuda, H.; Yoshikawa, M. J. Nat. Prod. 2004, 67, 1119.

    Article  CAS  PubMed  Google Scholar 

  53. Sripada, L.; Teske, J. A.; Deiters, A. Org. Biomol. Chem. 2008, 6, 263.

    Article  CAS  PubMed  Google Scholar 

  54. Guo, W.-S.; Dou, Q.; Hou, J.; Wen, L.-R.; Li, M. J. Org. Chem. 2017, 82, 7015.

    Article  CAS  PubMed  Google Scholar 

  55. Wu, J.; Gao, Y.; Zhao, X.; Zhang, L.; Chen, W.; Tang, G.; Zhao, Y. RSC Adv. 2016, 6, 303.

    Article  CAS  Google Scholar 

  56. Li, Y.-M.; Sun, M.; Wang, H.-L.; Tian, Q.-P.; Yang, S.-D. Angew. Chem., Int. Ed. 2013, 52, 3972.

    Article  CAS  Google Scholar 

  57. Li, Y.-M.; Shen, Y.; Chang, K.-J.; Yang, S.-D. Tetrahedron 2014, 70, 1991.

    Article  CAS  Google Scholar 

  58. Zhang, H.; Gu, Z.; Li, Z.; Pan, C.; Li, W.; Hu, H.; Zhu, C. J. Org. Chem. 2016, 81, 2122.

    Article  CAS  PubMed  Google Scholar 

  59. Li, Y.-M.; Wang, S.-S.; Yu, F.; Shen, Y.; Chang, K.-J. Org. Biomol. Chem. 2015, 13, 5376.

    Article  CAS  PubMed  Google Scholar 

  60. Zheng, J.; Zhang, Y.; Wang, D.; Cui, S. Org. Lett. 2016, 18, 1768.

    Article  CAS  PubMed  Google Scholar 

  61. Zhou, Z.-Z.; Zheng, L.; Yan, X.-B.; Jin, D.-P.; He, Y.-T.; Liang, Y.-M. Org. Biomol. Chem. 2016, 14, 4507.

    Article  CAS  PubMed  Google Scholar 

  62. Kong, W.; Merino, E.; Nevado, C. Angew. Chem., Int. Ed. 2014, 53, 5078.

    CAS  Google Scholar 

  63. Gao, Y.; Li, X.; Xu, J.; Wu, Y.; Chen, W.; Tang, G.; Zhao, Y. Chem. Commun. 2015, 1605.

  64. Gao, Y.; Li, X.; Chen, W.; Tang, G.; Zhao, Y. J. Org. Chem. 2015, 80, 11398.

    Article  CAS  PubMed  Google Scholar 

  65. Zhao, J.; Li, P.; Li, X.; Xia, C.; Li, F. Chem. Commun. 2016, 3661.

  66. Mao, L.; Li, Y.; Yang, S. Chin. J. Chem. 2017, 35, 316.

    Article  CAS  Google Scholar 

  67. Mi, X.; Wang, C.; Huang, M.; Zhang, J.; Wu, Y.; Wu, Y. Org. Lett. 2014, 16, 3356.

    Article  CAS  PubMed  Google Scholar 

  68. Zhang, P.; Zhang, L.; Gao, Y.; Tang, G.; Zhao, Y. RSC Adv. 2016, 6, 60922.

    Article  CAS  Google Scholar 

  69. Li, D.-P.; Pan, X.-Q.; An, L.-T.; Zou, J.-P.; Zhang, W. J. Org. Chem. 2014, 79, 1850.

    Article  CAS  PubMed  Google Scholar 

  70. Zhou, J.; Zhang, G.-L.; Zou, J.-P.; Zhang, W. Eur. J. Org. Chem. 2011, 3412.

  71. Wang, L.-J.; Wang, A.-Q.; Xia, Y.; Wu, X.-X.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2014, 50, 13998.

    Article  CAS  Google Scholar 

  72. Zhang, H.; Li, W.; Zhu, C. J. Org. Chem. 2017, 82, 2199.

    Article  CAS  PubMed  Google Scholar 

  73. Novikov, M.; Rostovskii, N.; Khlebnikov, A.; Yufit, D. S. Chem. Heterocycl. Compd. 2017, 53, 985. [Khim. Geterotsikl. Soedin. 2017, 53, 985.]

  74. Gulevich, A. V.; Gevorgyan, V. Chem. Heterocycl. Compd. 2012, 48, 17. [Khim. Geterotsikl. Soedin. 2012, 22.]

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The work was supported by the Russian Science Foundation (grant № 14-23-00016).

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, 8 Arbuzov St., Kazan, 420088, Russia

    Yulia H. Budnikova

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Correspondence to Yulia H. Budnikova.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(3), 269–279

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Budnikova, Y.H. Transition metal-promoted reactions of diarylphosphine oxides as a synthetic method for organophosphorus heterocyclic compounds. Chem Heterocycl Comp 54, 269–279 (2018). https://doi.org/10.1007/s10593-018-2261-7

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