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Facile Chlorination of Benzyl Alcohols Using 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) and Sulfonyl Chlorides

  • Kim, Hyung-Woo (Department of Nuclear Medicine, Cancer Research Institute, Seoul National University College of Medicine) ;
  • Lee, Yun-Sang (Department of Nuclear Medicine, Cancer Research Institute, Seoul National University College of Medicine) ;
  • Shetty, Dinesh (Department of Nuclear Medicine, Cancer Research Institute, Seoul National University College of Medicine) ;
  • Lee, Hak-Jeong (Department of Nuclear Medicine, Cancer Research Institute, Seoul National University College of Medicine) ;
  • Lee, Dong-Soo (Department of Nuclear Medicine, Cancer Research Institute, Seoul National University College of Medicine) ;
  • Chung, June-Key (Department of Nuclear Medicine, Cancer Research Institute, Seoul National University College of Medicine) ;
  • Lee, Myung-Chul (Department of Nuclear Medicine, Cancer Research Institute, Seoul National University College of Medicine) ;
  • Chung, Kyoo-Hyun (Department of Chemistry, Inha University) ;
  • Jeong, Jae-Min (Department of Nuclear Medicine, Cancer Research Institute, Seoul National University College of Medicine)
  • Received : 2010.06.04
  • Accepted : 2010.09.10
  • Published : 2010.11.20

Abstract

Keywords

References

  1. Norris, J. F.; Watt, M.; Thomas, R. J. Am. Chem. Soc. 1916, 38, 1071. https://doi.org/10.1021/ja02262a014
  2. Gilman, H.; Kirby, J. E. J. Am. Chem. Soc. 1929, 51, 3475. https://doi.org/10.1021/ja01386a043
  3. Burks, J. E., Jr. Phosphorus(V) Chloride In Encyclopedia of Reagents for Organic Synthesis; Paquette, L., Ed.; 2004; Wiley & Sons:New York.
  4. Anderson, A. G., Jr.; Owen, N. E. T.; Freenor, F. J.; Erickson, D. Synthesis 1976, 398.
  5. Tipson, R. S. J. Org. Chem. 1962, 27, 1449.
  6. Appel, R. Angew. Chem. Intl. Ed. 1975, 14, 801. https://doi.org/10.1002/anie.197508011
  7. Mitsunobu, O. Synthesis 1981, 1.
  8. Lee, J. G.; Kang K. K. J. Org. Chem. 1988, 53, 3634. https://doi.org/10.1021/jo00250a048
  9. Ha, D. S.; Chai, G. S. Bull. Korean Chem. Soc. 1997, 8, 1045.
  10. Ha, D. S.; Yoon, M. J. J. Korean Chem. Soc. 1997, 41, 541.
  11. Yasuda, M.; Yamasaki, S.; Onishi, Y.; Baba, A. J. Am. Chem. Soc. 2004, 126, 7186-7187. https://doi.org/10.1021/ja048688t
  12. Pearson, W. H.; Walavalkar, R. Tetrahedron 1994, 50, 12293-12304. https://doi.org/10.1016/S0040-4020(01)89538-7
  13. Larock, R. C.; Babu, S. Tetrahedron 1987, 43, 2013-2020. https://doi.org/10.1016/S0040-4020(01)86782-X
  14. Douty, B. D.; Salvmo, J. M.; Seoane, P. R.; Dolle, R. E. Bioorg. Med. Chem. Lett. 1995, 5, 363-366. https://doi.org/10.1016/0960-894X(95)00036-S
  15. Ballester, M.; Veciana, J.; Riera, J.; Castaiier, J.; Rovira, C.; Armet, O. J. Org. Chem. 1986, 51, 2472-2480. https://doi.org/10.1021/jo00363a013
  16. Armaroli, N.; Barigelletti, F.; Ceroni, P.; Eckert, J.-F.; Nierengarten, J.-F. Int. J. Photoenergy 2001, 3, 33-40. https://doi.org/10.1155/S1110662X01000046
  17. Watanabe, N.; Mizuno, T.; Matsumoto, M. Tetrahedron 2005, 61, 9569-9585. https://doi.org/10.1016/j.tet.2005.07.081
  18. Takaya, Y.; Terashima, K.; Ito, J.; He, Y.-H.; Tateoka, M.; Yamaguchi, N.; Niwa, M. Tetrahedron 2005, 61, 10285-10290. https://doi.org/10.1016/j.tet.2005.08.023
  19. Yasuda, M.; Yamasaki, S.; Onishi, Y.; Baba, A. Org. Synth. 2006, 83, 38-44. https://doi.org/10.15227/orgsyn.083.0038
  20. Crosignani, S.; Nadal, B.; Li, Z.; Linclau, B. Chem. Comm. 2003, 260-261.
  21. Kim, K.-S.; Kwon, O. Z.; Seo, G. Stud. Surf. Sci. Catal. 2004, 154C, 2966-2972.

Cited by

  1. ChemInform Abstract: Facile Chlorination of Benzyl Alcohols Using 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) and Sulfonyl Chlorides. vol.42, pp.14, 2011, https://doi.org/10.1002/chin.201114069
  2. Chemoenzymatic Route for the Synthesis of (S)‐Moprolol, a Potential β‐Blocker vol.28, pp.4, 2010, https://doi.org/10.1002/chir.22574