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Hydroamination of alkynes with aromatic amines catalyzed by digallane (dpp-bian)Ga—Ga(dpp-bian)

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Abstract

Digallane (dpp-bian)Ga—Ga(dpp-bian) (1) (dpp-bian is the 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene) catalyzes the addition of 4-chloroaniline to some terminal alkynes RC≡CH (R = Bun, Ph, 4-MeC6H4). The reaction orders in each of the substrates were found for the reaction of phenylacetylene with 4-chloroaniline catalyzed by compound 1. The reaction of compound 1 with phenylacetylene in a molar ratio of 1: 10 led to 1-[N-(2,6-diisopropylphenyl)imino]-2-(1-phenylethylidene)acenaphthene (5) and the compound [C12H6(NC6H3Pr2 i)(PhC=CH2)(PhC=CH)]Ga(C≡CPh)2 (6). The reaction of digallane 1 with phenylacetylene and aniline in a stoichiometric ratio of 1: 2: 2 gave bis-anilide (dpp-bian)-Ga[N(H)Ph]2 (7) in 40% yield. The compound (PhC≡C)3Ga·THF (9) was obtained by the reaction of three equivalents of sodium phenylacetylide (prepared in situ from phenylacetylene and sodium) with one equivalent of GaCl3 in tetrahydrofuran. Compounds 5—7 and 9 were characterized by IR spectroscopy, 1H NMR spectroscopy was used to characterize products 5, 6, and 9, whereas EPR spectroscopy was used for amide 7. The structures of compounds 5—7 and 9 were determined by single crystal X-ray diffraction analysis.

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References

  1. L. Huang, M. Arndt, K. Gooßen, H. Heydt, L. J. Gooßen, Chem. Rev., 2015, 115, 2596.

    Article  CAS  Google Scholar 

  2. A. Luihl, H. P. Nayek, S. Blechert, P. W. Roesky, Chem. Commun., 2011, 47, 8280.

    Article  Google Scholar 

  3. A. Luihl, L. Hartenstein, S. Blechert, P. W. Roesky, Organometallics, 2012, 31, 7109.

    Article  Google Scholar 

  4. Y. Zhao, M. Lin, Z. Chen, H. Pei, Y. Li, Y. Chen, X. Wang, L. Li, Y. Cao, Y. Zhanga, W. Lib, RSC Advances, 2012, 2, 144–150.

    Article  CAS  Google Scholar 

  5. I. Dubovyk, I. D. G. Watson, A. K. Yudin, J. Org. Chem., 2013, 78, 1559.

    Article  CAS  Google Scholar 

  6. P. D. Schweizer, H. Wadepohl, L. H. Gade, Organometallics, 2013, 32, 3697.

    Article  CAS  Google Scholar 

  7. M. V. Anokhin, A. V. Murashkina, A. D. Averin, I. P. Beletskaya, Mendeleev Commun., 2014, 24, 332.

    Article  CAS  Google Scholar 

  8. T. O. Petersen, E. Tausch, J. Schaefer, H. Scherer, P. W. Roesky, I. Krossing, Chem. Eur. J., 2015, 21, 13696.

    Article  CAS  Google Scholar 

  9. M. J. González, L. A. Lуpez, R. Vicente, Tetrahedron Lett., 2015, 56, 1600.

    Article  Google Scholar 

  10. E. Kumaran, W. K. Leong, Organometallics, 2015, 34, 1779.

    Article  CAS  Google Scholar 

  11. H. Tafazolian, D. C. Samblanet, J. A. R. Schmidt, Organometallics, 2015, 34, 1809.

    Article  CAS  Google Scholar 

  12. J. Bahri, R. Blieck, B. Jamoussi, M. Taillefer, F. Monnier, Chem. Commun., 2015, 51, 11210.

    Article  CAS  Google Scholar 

  13. J. C.-H. Yim, J. A. Bexrud, R. O. Ayinla, D. C. Leitch, L. L. Schafer, J. Org. Chem., 2014, 79, 2015.

    Article  CAS  Google Scholar 

  14. J. C.-H. Yim, L. L. Schafer, Eur. J. Org. Chem., 2014, 6825.

    Google Scholar 

  15. Q. Sun, Y. Wang, D. Yuan, Y. Yao, Q. Shen, Chem. Commun., 2015, 51, 7633.

    Article  CAS  Google Scholar 

  16. Q. Sun, Y. Wang, D. Yuan, Y. Yao, Q. Shen, Dalton Trans., 2015, 44, 20532. DOI: 10.1039/C5DT02643A.

    Article  Google Scholar 

  17. A. L. Reznichenko, H. N. Nguyen, K. C. Hultzsch, Angew. Chem., Int. Ed., 2010, 49, 8984.

    Article  CAS  Google Scholar 

  18. Y. Cao, Z. Du, W. Li, J. Li, Y. Zhang, F. Xu, Q. Shen, Inorg. Chem., 2011, 50, 3729.

    Article  CAS  Google Scholar 

  19. L. Xu, Z. Wang, W.-X. Zhang, Z. Xi, Inorg. Chem., 2012, 51, 11941.

    Article  CAS  Google Scholar 

  20. I. V. Basalov, S. C. Roşca, D. M. Lyubov, A. N. Selikhov, G. K. Fukin, Y. Sarazin, J.-F. Carpentier, A. A. Trifonov, Inorg. Chem., 2014, 53, 1654.

    Article  CAS  Google Scholar 

  21. P.-H. Wei, L. Xu, L.-C. Song, W.-X. Zhang, Z. Xi, Organometallics, 2014, 33, 2784.

    Article  CAS  Google Scholar 

  22. F. M. Sroor, C. G. Hrib, L. Hilfert, P. G. Jones, F. T. Edelmann, J. Organomet. Chem., 2015, 785, 1.

    Article  CAS  Google Scholar 

  23. E. M. Broderick, N. P. Gutzwiller, P. L. Diaconescu, Organometallics, 2010, 29, 3242.

    Article  CAS  Google Scholar 

  24. I. S. R. Karmel, M. Tamm, M. S. Eisen, Angew. Chem., Int. Ed., 2015, 54, 12422.

    Article  CAS  Google Scholar 

  25. C. Bour, V. Gandon, Coord. Chem. Rev., 2014, 279, 43.

    Article  CAS  Google Scholar 

  26. A. G. M. Barrett, C. Brinkmann, M. R. Crimmin, M. S. Hill, P. Hunt, P. A. Procopiou, J. Am. Chem. Soc., 2009, 131, 12906.

    Article  CAS  Google Scholar 

  27. J. Koller, R. G. Bergman, Organometallics, 2010, 29, 5946.

    Article  CAS  Google Scholar 

  28. C. Brinkmann, A. G. M. Barrett, M. S. Hill, P. A. Procopiou, J. Am. Chem. Soc., 2012, 134, 2193.

    Article  CAS  Google Scholar 

  29. B. Liu, T. Roisnel, J.-F. Carpentier, Y. Sarazin, Angew. Chem., Int. Ed., 2012, 51, 4943.

    Article  CAS  Google Scholar 

  30. X. Zhang, T. J. Emge, K. C. Hultzsch, Angew. Chem., Int. Ed., 2012, 51, 394.

    Article  CAS  Google Scholar 

  31. B. Liu, T. Roisnel, J.-F. Carpentier, Y. Sarazin, Chem. Eur. J., 2013, 19, 13445.

    Article  CAS  Google Scholar 

  32. A. Baishya, M. Kr. Barman, T. Peddarao, S. Nembenna, J. Organomet. Chem., 2014, 769, 112.

    Article  CAS  Google Scholar 

  33. N. Sakai, N. Takahashi, Y. Ogiwara, Eur. J. Org. Chem., 2014, 5078.

    Google Scholar 

  34. O. V. Kazarina, M. V. Moskalev, I. L. Fedushkin, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 32 [Izv. Akad. Nauk, Ser. Khim., 2015, 32].

    Article  CAS  Google Scholar 

  35. I. L. Fedushkin, A. A. Skatova, V. K. Cherkasov, V. A. Chudakova, S. Dechert, M. Hummert, H. Schumann, Chem. Eur. J., 2003, 9, 5778.

    Article  CAS  Google Scholar 

  36. I. L. Fedushkin, A. G. Morozov, O. V. Rassadin, G. K. Fukin, Chem. Eur. J., 2005, 11, 5749.

    Article  CAS  Google Scholar 

  37. I. L. Fedushkin, A. A. Skatova, M. Hummert, H. Schumann, Eur. J. Inorg. Chem., 2005, 1601.

    Google Scholar 

  38. I. L. Fedushkin, A. N. Lukoyanov, G. K. Fukin, M. Hummert, H. Schumann, Russ. Chem. Bull. (Int. Ed.), 2006, 55, 1177 [Izv. Akad. Nauk, Ser. Khim., 2006, 1134].

    Article  CAS  Google Scholar 

  39. I. L. Fedushkin, A. S. Nikipelov, K. A. Lyssenko, J. Am. Chem. Soc., 2010, 132, 7874.

    Article  CAS  Google Scholar 

  40. I. L. Fedushkin, A. S. Nikipelov, A. G. Morozov, A. A. Skatova, A. V. Cherkasov, G. A. Abakumov, Chem. Eur. J., 2012, 18, 255.

    Article  CAS  Google Scholar 

  41. L. Fedushkin, M. V. Moskalev, A. N. Lukoyanov, A. N. Tishkina, E. V. Baranov, G. A. Abakumov, Chem. Eur. J., 2012, 18, 11264.

    Article  CAS  Google Scholar 

  42. I. L. Fedushkin, M. V. Moskalev, E. V. Baranov, G. A. Abakumov, J. Organomet. Chem., 2013, 747, 235.

    Article  CAS  Google Scholar 

  43. I. L. Fedushkin, A. A. Skatova, V. A. Dodonov, V. A. Chudakova, N. L. Bazyakina, A. V. Piskunov, S. V. Demeshko, G. K. Fukin, Inorg. Chem., 2014, 53, 5159.

    Article  CAS  Google Scholar 

  44. I. L. Fedushkin, O. V. Kazarina, A. N. Lukoyanov, A. A. Skatova, N. L. Bazyakina, A. V. Cherkasov, E. Palamidis, Organometallics, 2015, 34, 1498.

    Article  CAS  Google Scholar 

  45. I. L. Fedushkin, M. V. Moskalev, A. A. Skatova, G. K. Fukin, G. A. Abakumov, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 731 [Izv. Akad. Nauk, Ser. Khim., 2013, 731].

    Article  CAS  Google Scholar 

  46. M. Schiefer, N. D. Reddy, H.-J. Ahn, A. Stasch, H. W. Roesky, A. C. Schlicker, H.-G. Schmidt, M. Noltemeyer, D. Vidovic, Inorg. Chem., 2003, 42, 4970.

    Article  CAS  Google Scholar 

  47. A. A. Skatova, I. L. Fedushkin, O. V. Maslova, M. Hummert, H. Schumann, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 2284 [Izv. Akad. Nauk, Ser. Khim., 2007, 1702].

    Article  CAS  Google Scholar 

  48. J. Scholz, S. Kahlert, H. Görls, Organometallics, 2004, 23, 1594.

    Article  CAS  Google Scholar 

  49. I. L. Fedushkin, V. A. Chudakova, G. K. Fukin, S. Dechert, M. Hummert, H. Schumann, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 2744 [Izv. Akad. Nauk, Ser. Khim., 2004, 2634].

    Article  CAS  Google Scholar 

  50. D. Solis-Ibarra, A. P. Gуmora-Figueroa, N. Zavala-Segovia, V. Jancik, Eur. J. Inorg. Chem., 2009, 4564.

    Google Scholar 

  51. G. M. Sheldrick, SHELXTL v. 6.12, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA, 2000.

    Google Scholar 

  52. G. M. Sheldrick, SADABS v. 2.01, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA, 1998.

    Google Scholar 

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Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603950, Nizhny Novgorod, Russian Federation

    M. V. Moskalev, A. A. Skatova, V. A. Chudakova, N. M. Khvoinova, N. L. Bazyakina, A. G. Morozov, O. V. Kazarina, A. V. Cherkasov, G. A. Abakumov & I. L. Fedushkin

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  1. M. V. Moskalev
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  2. A. A. Skatova
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  3. V. A. Chudakova
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  4. N. M. Khvoinova
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  5. N. L. Bazyakina
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  6. A. G. Morozov
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  7. O. V. Kazarina
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  8. A. V. Cherkasov
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  9. G. A. Abakumov
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  10. I. L. Fedushkin
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Correspondence to I. L. Fedushkin.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2830—2840, December, 2015.

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Moskalev, M.V., Skatova, A.A., Chudakova, V.A. et al. Hydroamination of alkynes with aromatic amines catalyzed by digallane (dpp-bian)Ga—Ga(dpp-bian). Russ Chem Bull 64, 2830–2840 (2015). https://doi.org/10.1007/s11172-015-1234-6

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  • DOI: https://doi.org/10.1007/s11172-015-1234-6

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