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Effective bimetallic composite catalysts for the synthesis of arylated furans and thiophenes in aqueous media

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Chemistry of Heterocyclic Compounds Aims and scope

N-(4,6-Dimethylpyrimidin-2-yl)-5-phenylisoxazole-3-carboxamide was used as a ligand for obtaining bimetallic boron-containing heterogeneous catalysts Pd–Ni(Co)–B–L (Ni(Co):Pd = 9:1). The obtained composites were highly active as catalysts of Suzuki reaction in aqueous media, allowing to develop convenient methods for the synthesis of heterobiaryls containing furyl and thienyl rings.

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Notes

  1. TON (turnover number) – the number of catalytic cycles, determined as the number of product molecules formed on one molecule (or atom) of the catalyst (a dimensionless quantity). TOF (turnover frequency) – the number of catalytic cycles in a unit of time.

References

  1. (a) Dheer, D.; Singh, V.; Shankar, R. Bioorg. Chem. 2017, 71, 30. (b) Sysak, A.; Obmińska-Mrukowicz, B. Eur. J. Med. Chem. 2017, 137, 292.

  2. (а) Bumagin, N. A.; Kletskov, A. V.; Petkevich, S. K.; Kolesnik, I. A.; Lyakhov, A. S.; Ivashkevich, L. S.; Baranovsky, A. V.; Kurman, P. V.; Potkin, V. I. Tetrahedron 2018, 74, 3578. a Bumagin, N. A.; Petkevich, S. K.; Kletskov, A. V.; Potkin, V. I. Chem. Heterocycl. Compd. 2017, 53, 1340. [Khim. Geterotsikl. Soedin. 2017, 53, 1340.] (c) Bumagin, N. A.; Potkin, V. I. Russ. Chem. Bull., Int. Ed. 2016, 65, 321. [Izv. Akad. Nauk, Ser. Khim. 2016, 321.] (d) Huang, D.; Zhao, P.; Astruc, D. Coord. Chem. Rev. 2014, 272, 145. b Bumagin, N. A.; Petkevich, S. K.; Kletskov, A. V.; Livantsov, M. V.; Golantsov, N. E.; Potkin, V. I. Chem. Heterocycl. Compd. 2013, 49, 1515. [Khim. Geterotsikl. Soedin. 2013, 1633.]

  3. (a) Suzuki, A.; Yamamoto, Y. Chem. Lett . 2011, 40, 894. (b) Kinzel, T.; Zhang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14073.

  4. (a) Pomel, V.; Klicic, J.; Covini, D.; Church, D. D.; Shaw, J. P.; Roulin, K.; Burgat-Charvillon, F.; Valognes, D.; Camps, M.; Chabert, C.; Gillieron, C.; Françon, B.; Perrin, D.; Leroy, D.; Gretener, D.; Nichols, A.; Vitte, P. A.; Carboni, S.; Rommel, C.; Schwarz, M. K.; Rückle, T. J. Med. Chem. 2006, 49, 3857. (b) Villain-Guillot, P.; Gualtieri, M.; Bastide, L.; Roquet, F.; Martinez, J.; Amblard, M.; Pugniere, M.; Leonetti, J.-P. J. Med. Chem. 2007, 50, 4195. (c) Katritzky, A. R.; Tala, S. R.; Lu, H.; Vakulenko, A. V.; Chen, Q.-Y.; Sivapackiam, J.; Pandya, K.; Jiang, S.; Debnath, A. K. J. Med. Chem. 2009, 52, 7631. (d) Sleebs, B. E.; Kersten, W. J. A.; Kulasegaram, S.; Nikolakopoulos, G.; Hatzis, E.; Moss, R. M.; Parisot, J. P.; Yang, H.; Czabotar, P. E.; Fairlie, W. D.; Lee, E. F.; Adams, J. M.; Chen, L.; van Delft, M. F.; Lowes, K. N.; Wei, A.; Huang, D. C. S.; Colman, P. M.; Street, I. P.; Baell, J. B.; Watson, K.; Lessene, G. J. Med. Chem. 2013, 56, 5514.

  5. Inzelt, G. Conducting Polymers: A New Era in Electrochemistry; Springer: Heidelberg, 2012, p. 23.

    Book  Google Scholar 

  6. Knapp, D. M.; Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2009, 131, 6961.

    Article  CAS  PubMed  Google Scholar 

  7. (a) Solodukhin, A. N.; Luponosov, Y. N.; Buzin, M. I.; Peregudova, S. M.; Svidchenko, E. A.; Ponomarenko, S. A. Mendeleev Commun. 2018, 28, 415. (b) Yamamoto, Y.; Takizawa, M.; Yu, X.-Q.; Miyaura, N. Angew. Chem., Int. Ed. 2008, 47, 928.

  8. Molander, G. A.; Canturk, B.; Kennedy, L. E. J. Org. Chem. 2009, 74, 973.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. (a) Bumagin, N. A.; Andryukhova, N. P.; Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1988, 37, 1285. [Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 1449.] (b) Bumagin, N. A.; More, P. G.; Beletskaya, I. P. J. Organomet. Chem. 1989, 371, 397. (c) Bumagin, N. A.; Bykov, V. V.; Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1989, 38, 2206. [Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 2394.] (d) Bumagin, N. A.; Bykov, V. V.; Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1990, 39, 2426. [Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2672.] (e) Roshchin, A. I.; Bumagin, N. A.; Beletskaya, I. P. Tetrahedron Lett. 1995, 36, 125. a Bumagin, N. A.; Bykov, V. V. Tetrahedron 1997, 53, 14437. b Bumagin, N. A.; Tsarev, D. A. Tetrahedron Lett. 1998, 39, 8155.

  10. (a) Casalnuovo, A. L.; Calabrese, J. C. J. Am. Chem. Soc. 1990, 112, 4324. (b) Safi, M.; Sinou, D. Tetrahedron Lett. 1991, 32, 2025. (c) Genet, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715.

  11. (a) Jeffery, T. Tetrahedron Lett. 1994, 35, 3051. (b) Bumagin, N. A.; Bykov, V. V.; Sukhomlinova, L. I.; Tolstaya, T. P.; Beletskaya, I. P. J. Organomet. Chem. 1995, 486, 259. (c) Bumagin, N. A.; Sukhomlinova, L. I.; Luzikova, E. V.; Tolstaya, T. P.; Beletskaya, I. P. Tetrahedron Lett. 1996, 37, 897. (d) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170.

  12. (a) Polshettiwar, V.; Decottignies, A.; Len, C.; Fihri, A. ChemSusChem 2010, 3, 502. (b) Lamblin, M.; Nassar-Hardy, L.; Hierso, J.-C.; Fouquet, E.; Felpin, F.-X. Adv. Synth. Catal. 2010, 352, 33. (c) Bakherad, M. Appl. Organomet. Chem. 2013, 27, 125.

  13. Leadbeater, N. E. Chem. Commun. 2005, 2881.

  14. (a) Leadbeater, N. E.; Marco, M. Org. Lett. 2002, 4, 2973. (b) Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. D. J. Org. Chem. 2005, 70, 161.

  15. Isley, N. A.; Gallou, F.; Lipshutz, B. H. J. Am. Chem. Soc. 2013, 135, 17707.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Rai, R. K.; Tyagi, D.; Gupta, K.; Singh, S. K. Catal. Sci. Technol. 2016, 6, 3341.

    Article  CAS  Google Scholar 

  17. (a) Bumagin, N. A.; Veselov, I. S.; Belov, D. S. Chem. Heterocycl. Compd. 2014, 50, 19. [Khim. Geterotsikl. Soedin. 2014, 24.] (b) Bumagin, N. A. Catal. Commun. 2016, 79, 17.

  18. (a) Potkin, V. I.; Bumagin, N. A.; Petkevich, S. K., Lyakhov, A. S.; Rudakov, D. A.; Livantsov, M. V.; Golantsov, N. E. Synthesis 2012, 151. (b) Potkin, V. I.; Bumagin, N. A.; Zelenkovskii, V. M.; Petkevich, S. K.; Livantsov, M. V.; Golantsov, N. E. Russ. J. Gen. Chem. 2014, 84, 1782. [Zh. Obshch. Khim. 2014, 84, 1546.] (c) Bumagin, N. A.; Zelenkovskii, V. M.; Kletskov, A. V.; Petkevich, S. K.; Dikusar, E. A.; Potkin, V. I. Russ. J. Gen. Chem. 2016, 86, 68. [Zh. Obshch. Khim. 2016, 86, 75.]

  19. (a) Bumagin, N. A.; Potkin, V. I.; Petkevich, S. K.; Kolesnik, I. A.; Livantsov, M. V.; Alekseev, R. S. Nauchniy Almanakh 2018, 10, 149. (b) Bumagin, N. A.; Potkin, V. I.; Petkevich, S. K.; Kolesnik, I. A.; Livantsov, M. V.; Alekseev, R. S. Nauchniy Almanakh 2018, 11, 118.

  20. Geng, J.; Jefferson, D. A.; Johnson, B. F. G. Chem. Commun. 2007, 969.

  21. (a) Kaplan, I. G.; Miranda, U. In Practical Aspects of Computational Chemistry II; Leszczynski, J.; Shukla, M. K., Eds.; Springer: Dordrecht, 2012, p. 361. (b) Lombardi, J. R.; Davis, B. Chem. Rev. 2002, 102, 2431.

  22. Schuchardt, K. L.; Didier, B. T.; Elsethagen, T.; Sun, L.; Gurumoorthi, V.; Chase, J.; Li, J.; Windus, T. L. J. Chem. Inf. Model. 2007, 47, 1045.

    Article  CAS  PubMed  Google Scholar 

  23. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A., Jr. J. Comput. Chem. 1993, 14, 1347.

    Article  CAS  Google Scholar 

  24. ChemCraft. https://www.chemcraftprog.com.

  25. (a) Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158. (b) Roy, L. E.; Hay, P. J.; Martin, R. L. J. Chem. Theory Comput. 2008, 4, 1029.

  26. Rai, R. K.; Gupta, K.; Tyagi, D.; Mahata, A.; Behrens, S.; Yang, X.; Xu, Q; Pathak, B; Singh, S. K. Catal. Sci. Technol. 2016, 6, 5567.

    Article  CAS  Google Scholar 

  27. Read, M. L.; Krapp, A.; Miranda, P. O.; Gundersen, L.-L. Tetrahedron 2012, 68, 1869.

    Article  CAS  Google Scholar 

  28. Dauben, W. G.; Tanabe, M. J. Am. Chem. Soc. 1953, 75, 4969.

    Article  CAS  Google Scholar 

  29. Korolev, D. N.; Bumagin, N. A. Tetrahedron Lett. 2005, 46, 5751.

    Article  CAS  Google Scholar 

  30. Marinozzi, M.; Carotti, A.; Sansone, E.; Macchiarulo, A.; Rosatelli, E.; Sardella, R.; Natalini, B.; Rizzo, G.; Adorini, L.; Passeri, D.; De Franco, F.; Pruzanski, M.; Pellicciari, R. Bioorg. Med. Chem. 2012, 20, 3429.

    Article  CAS  PubMed  Google Scholar 

  31. Naber, J. R.; Buchwald, S. L. Adv. Synth. Catal. 2008, 350, 957.

    Article  CAS  Google Scholar 

  32. Ismail, M. A. J. Chem. Res. 2006, 733.

  33. Fišera, L.; Leško, J.; Kováč, J.; Hrabovský, J.; Surá, J. Collect. Czech. Chem. Commun. 1977, 42, 105.

    Article  Google Scholar 

  34. Ajdačić, V.; Senerovic, L.; Vranić, M.; Pekmezovic, M.; ArsicArsnijevic, V.; Veselinovic, A.; Veselinovic, J.; Šolaja, B. A.; Nikodinovic-Runic, J.; Opsenica, I. M. Bioorg. Med. Chem. 2016, 24, 1277.

    Article  CAS  PubMed  Google Scholar 

  35. Solbakken, M.; Skramstad, J. Acta Chem. Scand. 1993, 47, 1214.

    Article  CAS  Google Scholar 

  36. Baghbanzadeh, M.; Pilger, C.; Kappe, C. O. J. Org. Chem. 2011, 76, 8138.

    Article  CAS  PubMed  Google Scholar 

  37. Smith, P. A. S.; Boyer, J. H. J. Am. Chem. Soc. 1951, 73, 2626.

    Article  CAS  Google Scholar 

  38. Prelog, V.; Metzler, O.; Jeger, O. Helv. Chim. Acta 1947, 30, 675.

    Article  CAS  PubMed  Google Scholar 

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This work was performed with financial support from the Russian Foundation for Basic Research (grant 18-5800013-Bel_a), the Belarusian Republican Foundation for Fundamental Research (grant Х18Р-010), and within the framework of RUDN University Program 5-100.

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Correspondence to Nikolay A. Bumagin or Vladimir I. Potkin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(6), 508–516

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Bumagin, N.A., Petkevich, S.K., Kletskov, A.V. et al. Effective bimetallic composite catalysts for the synthesis of arylated furans and thiophenes in aqueous media. Chem Heterocycl Comp 55, 508–516 (2019). https://doi.org/10.1007/s10593-019-02492-8

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