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Synthesis of Triazole Click Ligands for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides

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Abstract

A series of new triazole ligands has been synthesized via copper-catalyzed cycloaddition reaction of readily available azides and alkynes. The synthesized compounds were characterized by FTIR, 1H and 13C NMR, and high-resolution mass spectra. The ligands provided excellent yields (up to 92%) in the palladium-catalyzed Suzuki-Miyaura cross coupling of unactivated aryl chlorides with phenylboronic acid. 1-Benzyl-4-(2,6-dimethoxyphenyl)-lH-1,2,3-triazole was found to be the most effective ligand due to the presence of electron-donating 2,6-dimethoxyphenyl substituent, which made it possible to develop a highly active ligand-catalyst system for the Suzuki reaction of aryl chlorides.

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References

  1. Rostovtsev, V.V., Green, L.G., Fokin, V.V., and Sharpless, K.B., Angew. Chem., Int. Ed., 2002, vol. 41, p. 2596. doi 10.1002/1521-3773(20020715)41

    Article  CAS  Google Scholar 

  2. Bock, V.D., Hiemstra, H., and van Maarseveen, J.H., Eur. J. Org. Chem., 2006, vol. 2006, p. 51. doi 10.1002/ejoc.200500483

    Article  Google Scholar 

  3. Huisgen, R., Szeimies, G., and Mobius, L., Chem. Ber., 1967, vol. 100, p. 2494. doi 10.1002/cber.l9671000806

    Article  CAS  Google Scholar 

  4. Kolb, H.C. and Sharpless, K.B., Drug Discovery Today, 2003, vol. 8, p. 1128. doi 10.1016/S1359-6446(03)02933-7

    Article  CAS  Google Scholar 

  5. Wang, Q., Chan, T.R., Hilgraf, R., Fokin, V.V., Sharpless, K.B., and Finn, M, J. Am. Chem. Soc, 2003, vol. 125, p. 3192. doi 10.1021/ja021381e

    Article  CAS  Google Scholar 

  6. Himo, F., Lovell, T., Hilgraf, R., Rostovtsev, V.V., Noodleman, L., and Sharpless, K.B., J. Am. Chem. Soc, 2005, vol. 127, p. 210. doi 10.1021/ja0471525

    Article  CAS  Google Scholar 

  7. Fokin, V.V. and Matyjaszewski, K., Organic Chemistry: Breakthroughs and Perspectives, Ding, K. and Dai, L.-X., Eds., Weinheim: Wiley, 2012, p. 247. doi 10.1002/9783527664801.ch7

  8. Meldal, M., and Tornoe, C.W., Chem. Rev., 2008, vol. 108, p. 2952. doi 10.1021/cr0783479

    Article  CAS  Google Scholar 

  9. Tornoe, C.W., Christensen, C, and Meldal, M, J. Org. Chem., 2002, vol. 67, p. 3057. doi 10.1021/joOll 148j

    Article  CAS  Google Scholar 

  10. Agalave, S.G., Maujan, S.R., and Pore, V.S., Chem. Asian J., 2011, vol. 6, p. 2696. doi 10.1002/ asia.201100432

    Article  CAS  Google Scholar 

  11. Thirumurugan, P., Matosiuk, D., and Jozwiak, K., Chem. Rev., 2013, vol. 113, p. 4905. doi 10.1021/ cr200409f

    Article  CAS  Google Scholar 

  12. Duan, H., Sengupta, S., Petersen, J.L., Akhme-dov, N.G., and Shi, X., J. Am. Chem. Soc, 2009, vol. 131, p. 12100. doi 10.1021/ja9041093

    Article  CAS  Google Scholar 

  13. Ye, X., He, Z., Ahmed, T., Weise, K., Akhmedov, N.G., and Petersen, J.L., Chem. Sci., 2013, vol. 4, p. 3712. doi 10.1039/C3SC51211H

    Article  CAS  Google Scholar 

  14. Gu, Q., Al Mamari, H. H., Graczyk, K., Diers, E., and Ackermann, L., Angew. Chem., Int. Ed., 2014, vol. 53, p. 3868. doi 10.1002/anie.201311024

    Article  CAS  Google Scholar 

  15. Best, M.D., Biochemistry, 2009, vol. 48, p. 6571. doi 10.1021/bi9007726

    Article  CAS  Google Scholar 

  16. Chow, H.F., Lau, K.N., Ke, Z., Liang, Y., and Lo, C.M., Chem. Commun., 2010, vol. 46, p. 3437. doi 10.1039/ C0CC00083C

    Article  CAS  Google Scholar 

  17. Hua, Y. and Flood, A.H., Chem. Soc. Rev., 2010, vol. 39, p. 1262. doi 10.1039/B818033B

    Article  CAS  Google Scholar 

  18. Hein, J.E., and Fokin, V.V., Chem. Soc. Rev., 2010, vol. 39, p. 1302. doi:10.1039/B904091A

    Article  CAS  Google Scholar 

  19. Gulevich, A.V. and Gevorgyan, V., Angew. Chem., Int. Ed., 2013, vol. 52, p. 1371. doi 10.1002/anie.201209338

    Article  CAS  Google Scholar 

  20. Schulze, B. and Schubert, U.S., Chem. Soc. Rev., 2014, vol. 43, p. 2522. doi 10.1039/C3CS60386E

    Article  CAS  Google Scholar 

  21. Nolte, C, Mayer, P., and Straub, B.F., Angew. Chem., Int. Ed., 2007, vol. 46, p. 2101. doi 10.1002/ anie.200604444

    Article  CAS  Google Scholar 

  22. Donnelly, K.F., Petronilho, A., and Albrecht, M., Chem. Commun., 2013, vol. 49, p. 1145. doi 10.1039/ C2CC37881G

    Article  CAS  Google Scholar 

  23. Miura, M., Angew. Chem., Int. Ed., 2004, vol. 43, p. 2201. doi 10.1002/anie.200301753

    Article  CAS  Google Scholar 

  24. Christmann, U. and Vilar, R., Angew. Chem., Int. Ed., 2005, vol. 44, p. 366. doi 10.1002/anie.200461189

    Article  CAS  Google Scholar 

  25. Kumbhar, A., J. Org. Chem., 2017, vol. 848, p. 22. doi 10.1016/j.jorganchem.2017.07.009

    Article  CAS  Google Scholar 

  26. Littke, A.F., and Fu, G.C., Angew. Chem., Int. Ed., 2002, vol. 41, p. 4176. doi 10.1002/1521-3773 (20021115)41:224176::AID-ANIE41763.0.CO;2-U

    Article  CAS  Google Scholar 

  27. Yoshimura, N., Momotake, A., Shinohara, Y., Nishi-mura, Y., and Arai, T., Chem. Lett., 2008, vol. 37, p. 174. doi 10.1246/cl.2008.174

    Article  CAS  Google Scholar 

  28. Kurti, L., and Czako, B., Strategic Applications of Named Reactions in Organic Synthesis, Amsterdam: Elsevier, 2005.

    Google Scholar 

  29. Braga, A.A., Morgon, N.H., Ujaque, G., and Maseras, F., J. Am. Chem. Soc, 2005, vol. 127, p. 9298. doi 10.1021/ja050583i

    Article  CAS  Google Scholar 

  30. Miyaura, N., J. Organomet. Chem., 2002, vol. 653, p. 54. doi 10.1016/S0022-328X(02)01264-0

    Article  CAS  Google Scholar 

  31. Maury, J., Feray, L., Bertrand, M.P., Kapat, A., and Renaud, P., Tetrahedron, 2012, vol. 68, p. 9606. doi 10.1016/j.tet.2012.09.066

    Article  CAS  Google Scholar 

  32. Ngai, M.H., Yang, P.Y., Liu, K., Shen, Y., Wenk, M.R., and Yao, S.Q., Chem. Commun., 2010, vol. 46, p. 8335. doi 10.1039/C0CC01276A

    Article  CAS  Google Scholar 

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Acknowledgments

Financial support from the Higher Education Commission (HEC) of Pakistan to this project is gratefully appreciated.

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Authors and Affiliations

  1. Department of Chemistry, University of Agriculture, Faisalabad, Pakistan

    S. Jabeen, R. A. Khera & J. Iqbal

  2. Department of Biochemistry, University of Agriculture, Faisalabad, Pakistan

    M. Asgher

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  1. S. Jabeen
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  2. R. A. Khera
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  3. J. Iqbal
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  4. M. Asgher
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Correspondence to R. A. Khera.

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Jabeen, S., Khera, R.A., Iqbal, J. et al. Synthesis of Triazole Click Ligands for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides. Russ J Org Chem 55, 1416–1422 (2019). https://doi.org/10.1134/S1070428019090239

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  • DOI: https://doi.org/10.1134/S1070428019090239

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