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Reaction of 1-Iodoalkynes with Tin Metal: A New Approach to the Sn–Csp Bond Formation

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Abstract

Tin iodoalkynylides were synthesized by the reaction of 1-iodoalkynes with tin metal. The scope of the reaction and the composition of the resulting mixtures were studied. The formation of tin iodoalkynylides was confirmed by counter synthesis via the reaction of disproportionation of tetra(phenylethynyl)tin with tin tetraiodide. The compounds synthesized were characterized by means of 119Sn NMR spectroscopy.

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REFERENCES

  1. Piers, E., Walker, S.D., and Armbrust, R., J. Chem. Soc. Perkin Trans. 1, 2000, no. 5, p. 635. https://doi.org/10.1039/A909922K

    Article  Google Scholar 

  2. Shirakawa, E., Yoshida, H., Kurahashi, T., Nakao, Y., and Hiyama, T., J. Am. Chem. Soc., 1998, vol. 120, no. 12, p. 2975. https://doi.org/10.1021/ja974206k

    Article  CAS  Google Scholar 

  3. Jousseaume, B. and Villeneuve, P., Tetrahedron, 1989, vol. 45, no. 4, p. 1145. https://doi.org/10.1016/0040-4020(89)80023-7

    Article  CAS  Google Scholar 

  4. Kondo, Y., Uchiyama, D., Sakamoto, T., and Yamanaka, H., Tetrahedron Lett., 1989, vol. 30, no. 32, p. 4249. https://doi.org/10.1016/s0040-4039(01)80702-4

    Article  CAS  Google Scholar 

  5. Genady, A.R., Janzen, N., Banevicius, L., El-Gamal, M., El-Zaria, M.E., and Valliant, J.F., J. Med. Chem., 2016, vol. 59, no. 6, p. 2660. https://doi.org/10.1021/acs.jmedchem.5b01881

    Article  CAS  PubMed  Google Scholar 

  6. Cordovilla, C., Bartolome, C., Mart, M., and Espinet, P., ACS Catal., 2015, vol. 5, no. 5, p. 3040. https://doi.org/10.1021/acscatal.5b00448

    Article  CAS  Google Scholar 

  7. Kato, S.I., Kano, H., Irisawa, K.I., Yoshikawa, N., Yamamoto, R., Kitamura, C., Nara, D., Yamanobe, T., Uehara, H., and Nakamura, Y., Org. Lett., 2018, vol. 20, no. 23, p. 7530. https://doi.org/10.1021/acs.orglett.8b03290

    Article  CAS  PubMed  Google Scholar 

  8. Levashov, A.S., Buryi, D.S., Goncharova, O.V., Konshin, V.V., Dotsenko, V.V., and Andreev, A.A., New J. Chem., 2017, vol. 41, p. 2910. https://doi.org/10.1039/C6NJ03905G

    Article  CAS  Google Scholar 

  9. Levashov, A.S., Buryi, D.S., Konshin, V.V., Dotsenko, V.V., Aksenov, N.A., and Aksenova, I.V., Russ. J. Gen. Chem., 2017, vol. 87, no. 7, p. 1627. https://doi.org/10.1134/S1070363217070295

    Article  CAS  Google Scholar 

  10. Levashov, A.S., Aksenov, N.A., Aksenova, I.V., and Konshin, V.V., New J. Chem., 2017, vol. 41, p. 8297. https://doi.org/10.1039/C7NJ01376K

    Article  CAS  Google Scholar 

  11. Levashov, A.S. and Buryi, D.S., Tetrahedron Lett., 2017, vol. 58, no. 47, p. 4476. https://doi.org/10.1016/j.tetlet.2017.10.035

    Article  CAS  Google Scholar 

  12. Kai, Y., Oku, S., Tani, T., Sakurai, K., and Tsuchimoto, T., Adv. Synth. Catal., 2019. https://doi.org/10.1002/adsc.201900540

  13. Levashov, A.S., Andreev, A.A., Buryi, D.S., and Konshin, V.V., Russ. Chem. Bull., 2014, vol. 63, p. 775. https://doi.org/10.1007/s11172-014-0508-8

    Article  CAS  Google Scholar 

  14. Levashov, A.S., Andreev, A.A., and Konshin, V.V., Tetrahedron Lett., 2015, vol. 56, no. 14, p. 1870. https://doi.org/10.1016/j.tetlet.2015.02.095

    Article  CAS  Google Scholar 

  15. Thoonen, S.H.L., Deelman, B.J., and Koten, G., van, J. Organomet. Chem., 2004, vol. 689, no. 13, p. 2145. https://doi.org/10.1016/j.jorganchem.2004.03.027

    Article  CAS  Google Scholar 

  16. Shaikh, N.S., Parkin, S., and LehmLer, H., Organometallics, 2006, vol. 25, no. 17, p.4207. https://doi.org/10.1002/chin.200651178

    Article  CAS  Google Scholar 

  17. Nicholson, J.W. and Douek, J.A., J. Organomet. Chem., 1982, vol. 233, no. 2, p. 169. https://doi.org/10.1016/S0022-328X(00)82696-0

    Article  CAS  Google Scholar 

  18. Klabunde, K.J. and Murdock, T.O., J. Org. Chem., 1979, vol. 44, no. 22, p. 3901. https://doi.org/10.1021/jo01336a030

    Article  CAS  Google Scholar 

  19. Zakharkin, L.I. and Okhlobystin, O.Y., Russ. Chem. Bull., 1963, vol. 12, no. 12, p. 2027. https://doi.org/10.1007/bf00844003

    Article  Google Scholar 

  20. Wrackmeyer, B. and Kehr, G., Main Group Met. Chem., 1993, vol. 16, no. 5, p. 305.

    CAS  Google Scholar 

  21. Gallagher, W.P., Terstiege, I., and Maleczka, R.E., J. Am. Chem. Soc., 2001, vol. 123, no. 14, p. 3194. https://doi.org/10.1021/ja0035295

    Article  CAS  PubMed  Google Scholar 

  22. Liu, X., Chen, G., Li, C., and Liu, P., Synlett., 2018, vol. 29, no. 15, p. 2051. https://doi.org/10.1055/s-0037-1610259

    Article  CAS  Google Scholar 

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Funding

This study was financially supported by the Russian Foundation for Basic Research (project no. р_а 19-43-230009) and by the Administration of the Krasnodar Krai and Ministry of Education and Science of the Russian Federation (projectno. 4.4892.2017), and was carried out with the use of equipment of the “Diagnostics of the Structure and Properties of Nanomaterials” Scientific and Educational Center.

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Authors and Affiliations

  1. Kuban State University, 350040, Krasnodar, Russia

    A. R. Chikava, A. S. Levashov & V. V. Konshin

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  1. A. R. Chikava
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  2. A. S. Levashov
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  3. V. V. Konshin
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Correspondence to A. S. Levashov.

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Chikava, A.R., Levashov, A.S. & Konshin, V.V. Reaction of 1-Iodoalkynes with Tin Metal: A New Approach to the Sn–Csp Bond Formation. Russ J Gen Chem 90, 610–613 (2020). https://doi.org/10.1134/S1070363220040088

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