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Csp3–H Bond Functionalization of α-Bromo Ketones for the Synthesis of α-Keto Thioamides Using Elemental Sulfur

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Abstract

An efficient metal- and additive-free synthesis of α-keto thioamides has been developed via sulfur oxidation of the Csp3–H bond of α-bromo ketones with amines. This environmentally friendly strategy made it possible to synthesize a wide series of α-keto thioamides with broad functional group tolerance.

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REFERENCES

  1. Doyle, M.P. and Goldberg, K.I., Acc. Chem. Res., 2012, vol. 45, p. 777. https://doi.org/10.1021/ar300096z

    Article  CAS  PubMed  Google Scholar 

  2. Godula, K. and Sames, D., Science, 2006, vol. 312, p. 67. https://doi.org/10.1126/science.1114731

    Article  CAS  PubMed  Google Scholar 

  3. Jia, C., Kitamura, T., and Fujiwara, Y., Acc. Chem. Res., 2001, vol. 34, p. 633. https://doi.org/10.1021/ar000209h

    Article  CAS  PubMed  Google Scholar 

  4. Ramirez, T.A., Zhao, B.G., and Shi, Y., Chem. Soc. Rev., 2012, vol. 41, p. 931. https://doi.org/10.1039/C1CS15104E

    Article  CAS  PubMed  Google Scholar 

  5. Xue, X.S., Ji, P., Zhou, B., and Cheng, J., Chem Rev., 2017, vol. 117, p. 8622. https://doi.org/10.1021/acs.chemrev.6b00664

    Article  CAS  PubMed  Google Scholar 

  6. Nooshabadi, M., Aghapoor, K., Darabi, H.R., and Mojtahedi, M.M., Tetrahedron Lett., 1999, vol. 40, p. 7549. https://doi.org/10.1016/S0040-4039(99)01600-7

    Article  CAS  Google Scholar 

  7. Nguyen, T.B., Ermolenko, L., and Al-Mourabit, A., Org. Lett., 2012, vol. 14, p. 4274. https://doi.org/10.1021/ol3020368

    Article  CAS  PubMed  Google Scholar 

  8. Xu, H., Deng, H., Li, Z., Xiang, H., and Zhou, X., Eur. J. Org. Chem., 2013, vol. 2013, no. 31, p. 7054. https://doi.org/10.1002/ejoc.201301148

    Article  CAS  Google Scholar 

  9. Nguyen, T.B., Tran, M.Q., Ermolenko, L., and Al-Mourabit, A., Org. Lett., 2014, vol. 16, p. 310. https://doi.org/10.1021/ol403345e

    Article  CAS  PubMed  Google Scholar 

  10. Guntreddi, T., Vanjari, R., and Singh, K.N., Org. Lett., 2014, vol. 16, p. 3624. https://doi.org/10.1021/ol501482g

    Article  CAS  PubMed  Google Scholar 

  11. Banala, S. and Süssmuth, R.D., ChemBioChem, 2010, vol. 11, p. 1335. https://doi.org/10.1002/cbic.201000266

    Article  CAS  PubMed  Google Scholar 

  12. Kloss, F., Lincke, T., and Hertweck, C., Eur. J. Org. Chem., 2011, vol. 2011, p. 1429. https://doi.org/10.1002/ejoc.201001695

    Article  CAS  Google Scholar 

  13. Yang, G.F. and Yang, H.Z., Chin. J. Chem., 1999, vol. 17, p. 650. https://doi.org/10.1002/cjoc.19990170613

    Article  CAS  Google Scholar 

  14. Sharma, I. and Crich, D., J. Org. Chem., 2011, vol. 76, p. 6518. https://doi.org/10.1021/jo200497j

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Ravez, S., Corbet, C., Spillier, Q., Dutu, A., Robin, A.D., Mullarky, E., Cantley, L.C., Feron, O., and Frédérick, R., J. Med. Chem., 2017, vol. 60, p. 1591. https://doi.org/10.1021/acs.jmedchem.6b01166

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Ansari, M.A., Yadav, D., and Singh, M.S., J. Org. Chem., 2020, vol. 85, p. 8320. https://doi.org/10.1021/acs.joc.0c00378

    Article  CAS  PubMed  Google Scholar 

  17. Creary, X. and Zhu, C., J. Am. Chem. Soc., 1995, vol. 117, p. 5859. https://doi.org/10.1021/ja00126a029

    Article  CAS  Google Scholar 

  18. Gopinath, P., Watanabe, T., and Shibasaki, M., J. Org. Chem., 2012, vol. 77, p. 9260. https://doi.org/10.1021/jo301803h

    Article  CAS  PubMed  Google Scholar 

  19. Ganesh, M. and Seidel, D., J. Am. Chem. Soc., 2008, vol. 130, p. 16464. https://doi.org/10.1021/ja8063292

    Article  CAS  PubMed  Google Scholar 

  20. Cao, J.L. and Qu, J., J. Org. Chem., 2010, vol. 75, p. 3663. https://doi.org/10.1021/jo100435f

    Article  CAS  PubMed  Google Scholar 

  21. Sharma, I. and Crich, D., J. Org. Chem., 2010, vol. 75, p. 8383. https://doi.org/10.1021/jo101453y

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Xie, J., Okano, A., Pierce, J.G., James, R.C., Stamm, S., Crane, C.M., and Boger, D.L., J. Am. Chem. Soc., 2012, vol. 134, p. 1284. https://doi.org/10.1021/ja209937s

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Angehr, N.P., Goetschi, E., Gmuender, H., Hebeisen, P., Hennig, M., Kuhn, B., Luebbers, T., Reindl, P., Ricklin, F., and Schmitt-Hoffmann, A., J. Med. Chem., 2011, vol. 54, p. 2207. https://doi.org/10.1021/jm1014023

    Article  CAS  Google Scholar 

  24. Eilingsfeld, H., Seefelder, M., and Weidinger, H., Angew. Chem., 1960, vol. 72, p. 836. https://doi.org/10.1002/ange.19600722208

    Article  CAS  Google Scholar 

  25. Li, H.Z., Xue, W.J., and Wu, A.X., Tetrahedron, 2014, vol. 70, p. 4645. https://doi.org/10.1016/j.tet.2014.05.045

    Article  CAS  Google Scholar 

  26. Liu, W., Chen, C., and Zhou, P., ChemistrySelect, 2017, vol. 2, p. 5532. https://doi.org/10.1002/slct.201700866

    Article  CAS  Google Scholar 

  27. Tran, K.M., Nguyen, N.H.K., Bui, T.T., To, T.A., Phan, N.T.S., Le, H.V., and Nguyen, T.T., RSC Adv., 2020, vol. 10, p. 44743. https://doi.org/10.1039/D0RA08740H

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. Gan, L., Gao, Y., Wei, L., and Wan, J.P., J. Org. Chem., 2019, vol. 84, p. 1064. https://doi.org/10.1021/acs.joc.8b02670

    Article  CAS  PubMed  Google Scholar 

  29. Jswal, A., Preeti, A.K.S., and Singh, K.N., Asian J. Org. Chem., 2021, vol. 10, p. 1748.

    Article  Google Scholar 

  30. Yu, P., Wang, Y., Zeng, Z., and Chen, Y., J. Org. Chem., 2019, vol. 84, p. 14883. https://doi.org/10.1021/acs.joc.9b01777

    Article  CAS  PubMed  Google Scholar 

  31. Zhang, Z., Yang, J., Yu, R., Wu, K., Bu, J., Li, S., Qian, P., and Sheng, L., Eur. J. Org. Chem., 2021, vol. 2021, p. 5209. https://doi.org/10.1002/ejoc.202100993

    Article  CAS  Google Scholar 

  32. Saeidian, H., Vahdati-Khajehi, S., Bazghosha, H., and Mirjafary, Z., J. Sulfur Chem., 2014, vol. 35, p. 700. https://doi.org/10.1080/17415993.2014.955026

    Article  CAS  Google Scholar 

  33. Paul, N., Sathishkumar, R., Anuba, C., and Muthusubramanian, S., RSC Adv., 2013, vol. 3, p. 7445. https://doi.org/10.1039/C3RA21556C

    Article  CAS  Google Scholar 

  34. Priebbenow, D.L. and Bolm, C., Chem. Soc. Rev., 2013, vol. 42, p. 7870. https://doi.org/10.1039/C3CS60154D

    Article  CAS  PubMed  Google Scholar 

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Funding

Financial support by Scientific and Technology Innova­tion Programs of Higher Education Institutions in Shanxi (2020L0596, 2020L0587) is gratefully appreciated.

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Authors and Affiliations

  1. Department of Pharmacy, Changzhi Medical College, 046000, Changzhi, China

    Haiying Tian

  2. Department of Materials Science and Engineering, Jinzhong University, 030619, Jingzhong, China

    Fang Guo & Xiuling Chen

Authors
  1. Haiying Tian
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  2. Fang Guo
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  3. Xiuling Chen
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Correspondence to Xiuling Chen.

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Tian, H., Guo, F. & Chen, X. Csp3–H Bond Functionalization of α-Bromo Ketones for the Synthesis of α-Keto Thioamides Using Elemental Sulfur. Russ J Org Chem 58, 1260–1266 (2022). https://doi.org/10.1134/S107042802209010X

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  • DOI: https://doi.org/10.1134/S107042802209010X

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