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Synthesis of Diarylmethanes via Pd-Catalyzed Coupling of Aryltosylates with Benzyltitanium Reagents

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Abstract

Two new bidentate phosphate ligands have been synthesized by Pd-catalyzed coupling reactions, characterized and evaluated. An efficient and simple Pd-catalyzed synthetic method for diarylmethane derivatives in good to high yields and two new diarylmethanes is reported for the first time. It provides a wide range of substrates and exhibits good functional group tolerance. This method has been used for the synthesis of Beclobrate drug and is expected to find various applications in pharmaceutical synthesis and related areas.

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REFERENCES

  1. Ruiz-Castillo, P. and Buchwald, S.L., Chem. Rev., 2016, vol. 116, 12564. https://doi.org/10.1021/acs.chemrev.6b00512

  2. Piontek, A., Bisz, E., and Szostak, M., Angew. Chem. Int. Ed., 2018, vol. 57, no. 35, p. 11116. https://doi.org/10.1002/anie.201800364

  3. Whitaker, L., Harb, H.Y., and Pulis, A.P., Chem. Commun., 2017, vol. 53, no. 67, p. 9364. https://doi.org/10.1039/C7CC05037B

  4. Wang, T., Yang, S.W., Xu, S.L., Han, C.Y., Guo, G., and Zhao, J.F., RSC Adv., 2017, vol. 7, no. 26, p. 15805. https://doi.org/10.1039/C7RA02549A

  5. He, Z.Q., Song, F.F., Sun, H., and Huang, Y., J. Am. Chem. Soc., 2018, vol. 140, no. 7, p. 2693. https://doi.org/10.1021/jacs.8b00380

  6. Shirakawa, S. and Kobayashi, S., Org. Lett., 2006, vol. 8, no. 21, p. 4939. https://doi.org/10.1021/ol062031q

  7. Podder, S., Choudhury, J., Roy, U.K., and Roy, S., J. Org. Chem., 2007, vol. 72, no. 8, p. 3100. https://doi.org/10.1021/jo062633n

  8. Gao, J., Wang, J.Q., Song, Q.W., and He, L.N., Green Chem., 2011, vol. 13, no. 5, p. 1182. https://doi.org/10.1039/c1gc15056a

  9. Desroches, J., Champagne, P.A., Benhassine, Y., and Paquin, J.F., Org. Biomol. Chem., 2015, vol. 13, no. 8, p. 2243. https://doi.org/10.1039/C4OB02655A

  10. Wilsdorf, M., Leichnitz, D., and Reissig, H.U., Org. Lett., 2013, vol. 15, no. 10, p. 2494. https://doi.org/10.1021/ol400972m

  11. McGrew, G. I., Temaismithi, J., Carroll, P.J., and Walsh, P.J., Angew. Chem. Int. Ed., 2010, vol. 49, no. 32, p. 5541. https://doi.org/10.1002/anie.201000957

  12. Matthew, S.C., Glasspoole, B.W., Eisenberger, P., and Crudden, C.M., J. Am. Chem. Soc., 2014, vol. 136, no. 16, p. 5828. https://doi.org/10.1021/ja412159g

  13. Nambo, M. and Crudden, C.M., ACS Catal., 2015, vol. 5, no. 8, p. 4734. https://doi.org/10.1021/acscatal.5b00909

  14. Knochel, P., Millot, N., Rodriguez, A.L., and Tucker, C.E., in Organic Reactions, Knipe, A.C., Ed., New York: Wiley-VCH, 2001, p. 417.

  15. Jin, L., Xin, J., Huang, Z., He, J., and Lei, A., J. Am. Chem. Soc., 2010, vol. 132, no. 28, p. 9607. https://doi.org/10.1021/ja1045296

  16. Manolikakes, G., Dastbaravardeh, N., and Knochel, P., Synlett., 2007, vol. 13, p., 2077. https://doi.org/10.1055/s-2007-984906

  17. Varenikov, A. and Gandelman, M., J. Am. Chem. Soc., 2019, vol. 141, no. 28, p. 10994. https://doi.org/10.1021/jacs.9b05671

  18. Littke, A.F., in Modern Arylation Methods, Ackermann, L., Ed., Weinheim: Wiley-VCH, 2009, p. 25.

  19. Littke, A.F. and Fu, G.C., Angew. Chem. Int. Ed., 2002, vol. 41, no. 22, p. 4176. https://doi.org/10.1002/1521-3773(20021115)41:22%3C4176::AID-ANIE4176%3E3.0.CO;2-U

  20. Limmert, M.E., Roy, A.H., and Hartwig, J.F., J. Org. Chem., 2005, vol. 70, no. 23, p. 9364. https://doi.org/10.1021/jo051394l

  21. Naber, J.R., Fors, B.P., Wu, X.X., Gunn, J.T., and Buchwald, S.L., Heterocycles, 2010, vol. 80, no. 2, p. 215. https://doi.org/10.3987/COM-09-S(S)105

    Article  CAS  Google Scholar 

  22. Lee, H.W., So, C.M., Yuen, O.Y., Wong, W.T., and Kwong, F.Y., Org. Chem. Front., 2020, vol. 7, no. 7, p. 926. https://doi.org/10.1039/c9qo01537j

  23. Li, C.J., Russ. J. Gen. Chem., 2020, vol. 90, no. 4, p.725. https://doi.org/10.1134/s1070363220040258

  24. Bedford, R.B., Brenner, P.B., Carter, E., Clifton, J., Cogswell, P.M., Gower, N.J., Haddow, M.F., Harvey, J.N., Kehl, J.A., Murphy, D.M., Neeve, E.C., Neidig, M.L., Nunn, J., Snyder Benjamin, E.R., and Taylor, J., Organometallics, 2014, vol. 33, no. 20, p. 5767. https://doi.org/10.1021/om500518r

  25. Han, C. and Buchwald, S.L., J. Am. Chem. Soc., 2009, vol. 131, no. 22, p. 7532. https://doi.org/10.1021/ja902046m

  26. Krasovskiy, A. and Knochel, P., Angew. Chem. Int. Ed., 2004, vol. 43, no. 25, p. 3333. https://doi.org/10.1002/anie.200454084

  27. Krasovskiy, A. and Knochel, P., Synthesis, 2006, no. 5, p. 890. https://doi.org/10.1055/s-2006-926345

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The author gratefully acknowledges financial support from Hebei Chemical and Pharmaceutical College.

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  1. Department of Chemical and Environmental Engineering, Hebei Chemical and Pharmaceutical College, Shijiazhuang, 050026, Hebei, China

    He Zhang

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  1. He Zhang
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Zhang, H. Synthesis of Diarylmethanes via Pd-Catalyzed Coupling of Aryltosylates with Benzyltitanium Reagents. Russ J Gen Chem 92, 1340–1347 (2022). https://doi.org/10.1134/S1070363222070246

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