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Electrochemical Synthesis of gem-Bis(sulfenyl)enamines from Vinyl Azides and Thiols

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Abstract

Electrochemical synthesis of gem-bis(sulfenyl)enamines from vinyl azides and thiols is performed. The reaction occurs in an undivided electrochemical cell equipped with platinum electrodes in a DMSO–MeCN solution at a current density of 20 mA/cm2, using NH4I as a supporting electrolyte and a redox catalyst. The yields of the target products are 33–58%.

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REFERENCES

  1. Arnone, A., Cardillo, R., Di Modugno, V., and Nasini, G., J. Chem. Soc. Perkin Trans. 1, 1989, p. 1995. https://doi.org/10.1039/p19890001995

  2. Stallard, M.O., Fenical, W., and Kittredge, J.S., Tetrahedron, 1978, vol. 34, p. 2077. https://doi.org/10.1016/0040-4020(78)89006-1

    Article  CAS  Google Scholar 

  3. Scott, L.J. and Lamb, H.M., Drugs, 1999, vol. 58, p. 499. https://doi.org/10.2165/00003495-199958030-00016

    Article  CAS  PubMed  Google Scholar 

  4. Buckley, M.M. and Goa, K.L., Drugs, 1989, vol. 37, p. 451. https://doi.org/10.2165/00003495-198937040-00004

    Article  CAS  PubMed  Google Scholar 

  5. Chelucci, G., Chem. Rev., 2012, vol. 112, p. 1344. https://doi.org/10.1021/cr200165q

    Article  CAS  PubMed  Google Scholar 

  6. Pawluć, P., Hreczycho, G., Suchecki, A., Kubicki, M., and Marciniec, B., Tetrahedron, 2009, vol. 65, p. 5497. https://doi.org/10.1016/j.tet.2009.01.113

    Article  CAS  Google Scholar 

  7. Zhang, X., Liu, C., Deng, Y., and Cao, S., Org. Biomol. Chem., 2020, vol. 18, p. 7540. https://doi.org/10.1039/d0ob01821j

    Article  CAS  PubMed  Google Scholar 

  8. Yoo, W.J., Kondo, J., Rodriguez-Santamaria, J.A., Nguyen, T.V.Q., and Kobayashi, S., Angew. Chem. Int. Ed., 2019, vol. 58, p. 6772. https://doi.org/10.1002/anie.201902779

    Article  CAS  Google Scholar 

  9. Kumar, N., Eghbarieh, N., Stein, T., Shames, A.I., and Masarwa, A., Chem. Eur. J., 2020, vol. 26, p. 5360. https://doi.org/10.1002/chem.202000603

    Article  CAS  PubMed  Google Scholar 

  10. Zubkov, M.O., Kosobokov, M.D., Levin, V.V., Kokorekin, V.A., Korlyukov, A.A., Hu, J., and Dilman, A.D., Chem. Sci., 2020, vol. 11, p. 737. https://doi.org/10.1039/c9sc04643g

    Article  CAS  Google Scholar 

  11. Fu, J., Zanoni, G., Anderson, E.A., and Bi, X., Chem. Soc. Rev., 2017, vol. 46, p. 7208. https://doi.org/10.1039/c7cs00017k

    Article  CAS  PubMed  Google Scholar 

  12. Wang, Y.F., Lonca, G.H., and Chiba, S., Angew. Chem. Int. Ed., 2014, vol. 53, p. 1067. https://doi.org/10.1002/anie.201307846

    Article  CAS  Google Scholar 

  13. Paveliev, S.A., Churakov, A.I., Alimkhanova, L.S., Segida, O.O., Nikishin, G.I., and Terent’ev, A.O., Ad. Synth. Catal., 2020, vol. 362, p. 3864. https://doi.org/10.1002/adsc.202000618

    Article  CAS  Google Scholar 

  14. Mao, L.L., Quan, L.X., Zhu, X.H., Ji, C.B., Zhou, A.X., Chen, F.Y., and Zheng, D.G., Synlett, 2019, vol. 30, p. 955. https://doi.org/10.1055/s-0037-1611758

    Article  CAS  Google Scholar 

  15. Li, G., Kong, X., Liang, Q., Lin, L., Yu, K., Xu, B., and Chen, Q., Eur. J. Org. Chem., 2020, 2020, p. 6135. https://doi.org/10.1002/ejoc.202001059

  16. Ning, Y., Zhao, X.F., Wu, Y.B., and Bi, X., Org. Lett., 2017, vol. 19, p. 6240. https://doi.org/10.1021/acs.orglett.7b03204

    Article  CAS  PubMed  Google Scholar 

  17. Mulina, O.M., Zhironkina, N.V., Paveliev, S.A., Demchuk, D.V., and Terent’ev, A.O., Org. Lett., 2020, vol. 22, p. 1818. https://doi.org/10.1021/acs.orglett.0c00139

    Article  CAS  PubMed  Google Scholar 

  18. Mulina, O.M., Ilovaisky, A.I., Opatz, T., and Terent’ev, A.O., Tetrahedron Lett., 2021, vol. 64, p. 152737. https://doi.org/10.1016/j.tetlet.2020.152737

    Article  CAS  Google Scholar 

  19. Montevecchi, P.C., Navacchia, M.L., and Spagnolo, P., J. Org. Chem., 1997, vol. 62, p. 5846. https://doi.org/10.1021/jo970691q

    Article  CAS  Google Scholar 

  20. Terent’ev, A.O., Mulina, O.M., Ilovaisky, A.I., Kokorekin, V.A., and Nikishin, G.I., Mendeleev Commun., 2019, vol. 29, p. 80. https://doi.org/10.1016/j.mencom.2019.01.027

    Article  CAS  Google Scholar 

  21. Liu, K., Song, C., and Lei, A., Org. Biomol. Chem., 2018, vol. 16, p. 2375. https://doi.org/10.1039/C8OB00063H

    Article  CAS  PubMed  Google Scholar 

  22. Tang, H.T., Jia, J.S., and Pan, Y.M., Org. Biomol. Chem., 2020, vol. 18, p. 5315. https://doi.org/10.1039/d0ob01008a

    Article  CAS  PubMed  Google Scholar 

  23. Martins, G.M., Meirinho, A.G., Ahmed, N., Braga, A.L., and Mendes, S.R., ChemElectroChem., 2019, vol. 6, p. 5928. https://doi.org/10.1002/celc.201901525

    Article  CAS  Google Scholar 

  24. Pramanik, M., Choudhuri, K., and Mal, P., Org. Biomol. Chem., 2020, vol. 18, p. 8771. https://doi.org/10.1039/d0ob01741h

    Article  CAS  PubMed  Google Scholar 

  25. Hayashi, H., Kaga, A., and Chiba, S., J. Org. Chem., 2017, vol. 82, p. 11981. https://doi.org/10.1021/acs.joc.7b02455

    Article  CAS  PubMed  Google Scholar 

  26. Ni, J., Mao, X., and, Zhang, A., Adv. Synth. Catal., 2019, vol. 361, p. 2004. https://doi.org/10.1002/adsc.201900035

    Article  CAS  Google Scholar 

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Funding

The work was financially supported by the Russian Foundation for Basic Research (project no. 19-29-08027).

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Authors and Affiliations

  1. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia

    O. M. Mulina & M. M. Doronin

  2. Mendeleev University of Chemical Technology of Russia, 125047, Moscow, Russia

    V. A. Kostyagina

  3. Southwest State University, 305040, Kursk, Russia

    G. P. Timofeev

Authors
  1. O. M. Mulina
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  2. M. M. Doronin
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  3. V. A. Kostyagina
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  4. G. P. Timofeev
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Corresponding author

Correspondence to O. M. Mulina.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 8, pp. 1185–1192 https://doi.org/10.31857/S0514749221080103.

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Mulina, O.M., Doronin, M.M., Kostyagina, V.A. et al. Electrochemical Synthesis of gem-Bis(sulfenyl)enamines from Vinyl Azides and Thiols. Russ J Org Chem 57, 1302–1308 (2021). https://doi.org/10.1134/S1070428021080108

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  • DOI: https://doi.org/10.1134/S1070428021080108

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