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Russian Journal of General Chemistry

, Volume 88, Issue 4, pp 758–766 | Cite as

Highly Efficiently Synthesis of Disubstituted Pyrrole Derivatives via Rh(III)-Catalyzed Direct C–H Alkylation Under Mild Conditions

  • L. Wang
  • Zh. Li
  • X. Qu
  • W. M. Peng
  • Si Q. Hu
  • F. Wang
Article
  • 6 Downloads

Abstract

A mild and highly efficient Rh(III)-catalyzed direct C–H alkylation of pyrroles with diazo compounds has been developed. This green and atom-economic catalytic process enables an efficient access to various densely functionalized pyrrole derivatives in good to excellent yields, and it is potentially applicable to the large-scale synthesis of pyrrole derivatives.

Keywords

rhodium C–H alkylation pyrrole diazo compound 

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Notes

Acknowledgments

This work was supported by the National Science Foundation of China (no. 21302064) and Scientific Research Project of Hubei Provincial Department of Education (no. B2015231)

References

  1. 1.
    Regina, G.L, Silvestri, R., Artico, M., Lavecchia, A., Novellino, E., Befani, O., Turini, P., and Agostinelli, E., J. Med. Chem., 2007, vol. 50, p. 922. doi 10.1021/jm060882yCrossRefGoogle Scholar
  2. 2.
    Walsh, C.T, Garneau-Tsodikova, S., and Howard-Jones, A.R., Nat. Prod. Rep., 2006, vol. 23, p. 517. doi 10.1039/B605245MCrossRefGoogle Scholar
  3. 3.
    Facchetti, A., Abboto, A., Beverina, L., van der Boom, M.E, Dutta, P., Evmenenko, G., Pagani, G.A., and Marks, T.J., Chem. Mater., 2003, vol. 15, p. 1064. doi 10.1021/cm020929dCrossRefGoogle Scholar
  4. 4.
    Gabriel, S., Cécius, M., Fleury-Frenette, K., Cossement, D., Hecq, M., Ruth, N., Jérôme, R., and Jérôme, C., Chem. Mater., 2007, vol. 19, p. 2364. doi 10.1021/m062450hCrossRefGoogle Scholar
  5. 5.
    Gale, P.A., Acc. Chem. Res., 2006, vol. 39, p. 465. doi 10.1021/ar040237qCrossRefGoogle Scholar
  6. 6.
    Fan, H., Peng, J., Hamann, M.T., and Hu, J.F., Chem. Rev., 2008, vol. 108, p. 264. doi 10.1021/cr078199mCrossRefGoogle Scholar
  7. 7.
    Zhang, F.L., Hong, K., Li, T J., Park, H., and Yu, J.Q., Science, 2016, vol. 351, p. 252. doi 10.1126/science.aad7893CrossRefGoogle Scholar
  8. 8.
    Wang, X.C, Gong, W., Fang, L.Z., Zhu, R.Y., Li, S., Engle, K.M., and Yu, J.Q., Nature, 2015, vol. 519, p. 334. doi 10.1038/nature14214CrossRefGoogle Scholar
  9. 9.
    Rakshit, S., Patureau, F.W., and Glorius, F., J. Am. Chem. Soc, 2010, vol. 132, p. 9585. doi 10.1021/ja104305sCrossRefGoogle Scholar
  10. 10.
    Stuart, D.R., Alsabeh, P., Kuchn, M., and Fagnou, K., J. Am. Chem. Soc., 2010, vol. 132, p. 18326. doi 10.1021/ja1082624CrossRefGoogle Scholar
  11. 11.
    Wang, L. and Ackermann, L., Org. Lett., 2013, vol. 15, p. 176. doi 10.1021/ol303224eCrossRefGoogle Scholar
  12. 12.
    Li, B., Wang, N., Liang, Y., Xu, S., and Wang, B., Org. Lett., 2013, vol. 15, p. 136. doi 10.1021/ol303159hCrossRefGoogle Scholar
  13. 13.
    Deprez, N.R, Kalyani, D., Krause, A., and Sanford, M.S., J. Am. Chem. Soc., 2006, vol. 128, p. 4972. doi 10.1021/ja060809xCrossRefGoogle Scholar
  14. 14.
    Ackermann, L. and Lygin, A.V., Org. Lett., 2011, vol. 13, p. 3332. doi 10.1021/ol2010648CrossRefGoogle Scholar
  15. 15.
    Lu, M.Z., Lu, P., Xu, Y.H., and Loh, T.P., Org Lett, 2014, vol. 16, p. 2614. doi 10.1021/ol500754hCrossRefGoogle Scholar
  16. 16.
    Wang, L., Li, Z., Qu, X., and Peng, W.M., Chin. J. Chem., 2015, vol. 33, p. 1015. doi 10.1002/cjoc.201500354CrossRefGoogle Scholar
  17. 17.
    Gong, B., Shi, J., Wang, X., Yan, Y., Li, Q., Meng, Y., Xu, H.E., and Yi, W., Adv. Synth. Catal., 2014, vol. 356, p. 137. doi 10.1002/adsc.201300700CrossRefGoogle Scholar
  18. 18.
    Yang, L., Zhang, G., and Huang, H., Adv. Synth. Catal., 2014, vol. 356, p. 1509. doi 10.1002/adsc.201301107CrossRefGoogle Scholar
  19. 19.
    Davies, H.M.L and Hedley, S.J., Chem. Soc. Rev., 2007, vol. 36, p. 1109. doi 10.1039/B607983KCrossRefGoogle Scholar
  20. 20.
    Doyle, M.P., Duffy, R., Ratnikov, M., and Zhou, L., Chem. Rev., 2010, vol. 110, p. 704. doi 10.1021/cr900239nCrossRefGoogle Scholar
  21. 21.
    Chan, W.W., Lo, S.F., Zhou, Z., and Yu, W.Y., J. Am. Chem. Soc., 2012, vol. 134, p. 13565. doi 10.1021/ja305771yCrossRefGoogle Scholar
  22. 22.
    Hyster, T.K., Ruhl, K.E., and Rovis, T.A., J. Am. Chem. Soc., 2013, vol. 135, p. 5364. doi 10.1021/ja402274gCrossRefGoogle Scholar
  23. 23.
    Shi, Z., Koester, D.C., Boultadakis-Arapinis, M., and Glorius, F., J. Am. Chem. Soc., 2013, vol. 135, p. 12204. doi 10.1021/ja406338rCrossRefGoogle Scholar
  24. 24.
    Yu, X., Yu, S., Xiao, J., Wan, B., and Li, X., J. Org. Chem., 2013, vol. 78, p. 5444. doi 10.1021/jo400572hCrossRefGoogle Scholar
  25. 25.
    Liu, X.G., Zhang, S.S., Wu, J.Q., Li, Q., and Wang, H., Tetrahedron Lett., 2015, vol. 56, p. 4093. doi 10.1016/j.tetlet.2015.05.025CrossRefGoogle Scholar
  26. 26.
    Wang, L., Li, Z., Qu, X., Peng, W.M., Hu, S.Q., and Wang, H.B., Tetrahedron Lett., 2015, vol. 56, p. 6214. doi 10.1016/j.tetlet.2015.09.091CrossRefGoogle Scholar
  27. 27.
    Colby, D.A., Berman, R.G., and Ellman, J.A., Chem. Rev., 2010, vol. 110, p. 624. doi 10.1021/cr900005nCrossRefGoogle Scholar
  28. 28.
    Cho, S.H., Kim, J.Y., Kwak, J., and Chang, S., Chem. Soc. Rev., 2011, vol. 40, p. 5068. doi 10.1039/C1CS15082KCrossRefGoogle Scholar
  29. 29.
    Yeung, C.S. and Dong, V.M., Chem. Rev., 2011, vol. 111, p. 1215. doi 10.1021/cr100280dCrossRefGoogle Scholar
  30. 30.
    Song, G., Wang, F., and Li, X., Chem. Soc. Rev., 2012, vol. 41, p. 3651. doi 10.1039/2CS15281ACrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • L. Wang
    • 1
  • Zh. Li
    • 1
  • X. Qu
    • 1
  • W. M. Peng
    • 1
  • Si Q. Hu
    • 1
  • F. Wang
    • 2
  1. 1.Key Laboratory of Optoelectronic Chemical Materials and Devices, Ministry of Education, School of Chemical and Environmental EngineeringJianghan UniversityWuhanChina
  2. 2.College of Chemistry and Materials ScienceHubei Engineering UniversityXiaoganChina

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