Bulletin of the Korean Chemical Society

대한화학회 (Korean Chemical Society)
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One-Pot Homo- and Cross-Coupling Reactions of Arenediazonium Tosylate Salts for the Synthesis of Biaryls and Polyaryls

  • 투고 : 2011.03.14
  • 심사 : 2011.04.01
  • 발행 : 2011.08.20
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초록

One-pot homo- and cross-coupling reactions of arenediazonium tosylate salts bearing a halogen group have been exploited for the synthesis of biaryls and polyaryls under mild conditions. $Pd(OAc)_2$ has proven to be an efficient catalyst for the successful dual transformation of diazonium salts into p-quaterphenyl (3).

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참고문헌

  1. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. https://doi.org/10.1021/cr000664r
  2. Yamamoto, T. Synlett 2003, 425.
  3. Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem. Int. Ed. Engl. 1990, 29, 977. https://doi.org/10.1002/anie.199009771
  4. Ichimura, K. Chem. Rev. 2000, 100, 1847. https://doi.org/10.1021/cr980079e
  5. Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem. Int. Ed. 1998, 37, 402. https://doi.org/10.1002/(SICI)1521-3773(19980302)37:4<402::AID-ANIE402>3.0.CO;2-9
  6. Nelson, T. D.; Crouch, R. D. Org. React. 2004, 63, 265.
  7. Hassan, J.; Hathroubi, C.; Gozzi, C.; Lemaire, M. Tetrahedron 2001, 57, 7845. https://doi.org/10.1016/S0040-4020(01)00752-9
  8. Penalva, V.; Hassan, J.; Lavenot, L.; Gozzi, C.; Lemaire, M. Tetrahedron Lett. 1998, 39, 2559. https://doi.org/10.1016/S0040-4039(98)00196-8
  9. Wang, L.; Zhang , Y.; Liu, L.; Wang, Y. J. Org. Chem. 2006, 71, 1284. https://doi.org/10.1021/jo052300a
  10. Ram, R. N.; Singh, V. Tetrahedron Lett. 2006, 47, 7625. https://doi.org/10.1016/j.tetlet.2006.08.056
  11. Hennings, D. D.; Iwama, T.; Rawal, V. H. Org. Lett. 1999, 1, 1205. https://doi.org/10.1021/ol990872+
  12. Venkatraman, S.; Li, C. -J. Org. Lett. 1999, 1, 1133. https://doi.org/10.1021/ol9909740
  13. Jutand, A.; Mosleh, A. J. Org. Chem. 1997, 62, 261. https://doi.org/10.1021/jo961464b
  14. Kende, A. S.; Liebeskind, L. S.; Braitsch, D. M. Tetrahedron Lett. 1975, 16, 3375. https://doi.org/10.1016/S0040-4039(00)91402-3
  15. Cheng, K.; Xin, B.; Zhang, Y. J. Molecular Catalysis A. Chemical 2007, 273, 240. https://doi.org/10.1016/j.molcata.2007.03.031
  16. Xu, Z.; Mao. J.; Zhang, Y. Catalysis Comm. 2008, 9, 97. https://doi.org/10.1016/j.catcom.2007.05.008
  17. Darses, S.; Michaud, G.; Genet, J.-P. Eur. J. Org. Chem. 1999, 1875.
  18. Cepanec, I.; Litviae, M.; Udikoviae, J.; Pogoreliae, I.; Lovriae, M. Tetrahedron 2007, 63, 5614. https://doi.org/10.1016/j.tet.2007.04.016
  19. Robinson, M. K.; Kochurina, V. S.; Hanna, J. M., Jr. Tetrahedron Lett. 2007, 48, 7687. https://doi.org/10.1016/j.tetlet.2007.08.083
  20. Taylor, R. H.; Felpin, F. -X. Org. Lett. 2007, 9, 2911. https://doi.org/10.1021/ol0712733
  21. Ganesamoorthy, C.; Mague, J. T.; Balakrishna, M. S. Eup. J. Inorg. Chem. 2008, 596.
  22. Basu, B.; Das, P.; Bhuiyan, M. M. H.; Jha, S. Tetrahedron Lett. 2003, 44, 3817. https://doi.org/10.1016/S0040-4039(03)00731-7
  23. Filimonov, V. D.; Trusova, M.; Postnikov, P.; Krasnokutskaya, E. A.; Lee, Y. M.; Hwang, H. Y.; Hyunuk, K.; Chi, K. -W. Org. Lett. 2008, 10, 3961. https://doi.org/10.1021/ol8013528
  24. Lee, Y. M.; Moon, M. E.; Vajpayee, V.; Filimonov, V. D.; Chi, K. -W. Tetrahedron 2010, 66, 7418. https://doi.org/10.1016/j.tet.2010.07.005
  25. Moon, M. E.; Choi, Y.; Lee, Y. M.; Vajpayee, V.; Trusova, M.; Filimonov, V. D.; Chi, K. -W. Tetrahedron Lett. 2010, 51, 6769. https://doi.org/10.1016/j.tetlet.2010.10.099
  26. Liu, L.; Zhang, Y.; Xin, B. J. Org. Chem. 2006, 71, 3994. https://doi.org/10.1021/jo060122v
  27. Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405. https://doi.org/10.1021/jo960058p
  28. Felpin, F. -X.; Fouquet, E. Adv. Synth. Catal. 2008, 350, 863. https://doi.org/10.1002/adsc.200800025
  29. Ullmann, F.; Meyer, G. M. Ann. 1904, 332, 52.

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  2. Synthesis, Structure, and Synthetic Potential of Arenediazonium Trifluoromethanesulfonates as Stable and Safe Diazonium Salts vol.2019, pp.4, 2019, https://doi.org/10.1002/ejoc.201800887
  3. Biaryl synthesis with arenediazonium salts: cross-coupling, CH-arylation and annulation reactions vol.48, pp.4, 2019, https://doi.org/10.1039/C8CS00453F
  4. First Study of the Thermal and Storage Stability of Arenediazonium Triflates Comparing to 4-Nitrobenzenediazonium Tosylate and Tetrafluoroborate by Calorimetric Methods vol.23, pp.11, 2019, https://doi.org/10.1021/acs.oprd.9b00307