Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

One-Pot Synthesis of Naphthalenes from Baylis-Hillman Adducts via Pd-Mediated Successive Allylation and Arylation

  • Gowrisankar, Saravanan (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Ko-Hoon (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • Published : 2008.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891 https://doi.org/10.1021/cr010043d
  2. Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627-645 https://doi.org/10.2174/1385272023374094
  3. Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1481-1490 https://doi.org/10.5012/bkcs.2005.26.10.1481
  4. Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511-4574 https://doi.org/10.1016/j.tet.2008.02.087
  5. Rajesh, S.; Banerji, B.; Iqbal, J. J. Org. Chem. 2002, 67, 7852-7857 https://doi.org/10.1021/jo010981d
  6. Roy, O.; Riahi, A.; Henin, F.; Muzart, J. Tetrahedron 2000, 56, 8133-8140 https://doi.org/10.1016/S0040-4020(00)00727-4
  7. Reddy, C. R.; Kiranmai, N.; Babu, G. S. K.; Sarma, G. D.; Jagadeesh, B.; Chandrasekhar, S. Tetrahedron Lett. 2007, 48, 215-218 https://doi.org/10.1016/j.tetlet.2006.11.061
  8. Park, Y. S.; Cho, M. Y.; Kwon, Y. B.; Yoo, B. W.; Yoon, C. M. Synth. Commun. 2007, 37, 2677-2685 https://doi.org/10.1080/00397910701465370
  9. Kumareswaran, R.; Vankar, Y. D. Synth. Commun. 1998, 28, 2291-2302 https://doi.org/10.1080/00397919808007047
  10. Park, J. B.; Ko, S. H.; Kim, B. G.; Hong, W. P.; Lee, K-.J. Bull. Korean Chem. Soc. 2004, 25, 27-28
  11. Jousse-Karinthi, C.; Zouhiri, F.; Mahuteau, J.; Desmaele, D. Tetrahedron 2003, 59, 2093-2099 https://doi.org/10.1016/S0040-4020(03)00186-8
  12. Ross, J.; Xiao, J. Chem. Eur. J. 2003, 9, 4900-4906 https://doi.org/10.1002/chem.200304895
  13. Giambastiani, G.; Poli, G. J. Org. Chem. 1998, 63, 9608-9609 https://doi.org/10.1021/jo981599c
  14. Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: Chichester, 2004
  15. Ciufolini, M. A.; Browne, M. E. Tetrahedron Lett. 1987, 28, 171-173 https://doi.org/10.1016/S0040-4039(00)95678-8
  16. Ciufolini, M. A.; Qi, H.-B.; Browne, M. E. J. Org. Chem. 1988, 53, 4149-4151 https://doi.org/10.1021/jo00252a064
  17. Muratake, H.; Natusme, M.; Nakai, H. Tetrahedron 2004, 60, 11783-11803 https://doi.org/10.1016/j.tet.2004.09.112
  18. Gowrisankar, S.; Lee, H. S.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2008, 49, 1670-1673 https://doi.org/10.1016/j.tetlet.2007.12.133
  19. Kim, J. M.; Kim, K. H.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 3248-3251 https://doi.org/10.1016/j.tetlet.2008.03.102
  20. Gowrisankar, S.; Lee, H. S.; Lee, K. Y.; Lee, J.-E.; Kim, J. N. Tetrahedron Lett. 2007, 48, 8619-8622 https://doi.org/10.1016/j.tetlet.2007.10.043
  21. Lee, H. S.; Kim, S. H.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 1773-1776 https://doi.org/10.1016/j.tetlet.2008.01.058
  22. Kim, H. S.; Gowrisankar, S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 3858-3861 https://doi.org/10.1016/j.tetlet.2008.04.080
  23. Lee, H. S.; Kim, S. H.; Gowrisankar, S.; Kim, J. N. Tetrahedron 2008, 64, 7183-7190 https://doi.org/10.1016/j.tet.2008.05.087
  24. Tietze, L. F.; Redert, T.; Bell, H. P.; Hellkamp, S.; Levy, L. M. Chem. Eur. J. 2008, 14, 2527-2535 https://doi.org/10.1002/chem.200701676
  25. Tietze, L. F.; Nordmann, G. Eur. J. Org. Chem. 2004, 3247-3253
  26. Cavicchioli, M.; Decortiat, S.; Bouyssi, D.; Gore, J.; Balme, G. Tetrahedron 1996, 52, 11463-11478 https://doi.org/10.1016/0040-4020(96)00637-0
  27. Bruyere, D.; Gaignard, G.; Bouyssi, D.; Balme, G. Tetrahedron Lett. 1997, 38, 827-830 https://doi.org/10.1016/S0040-4039(96)02442-2
  28. Im, Y. J.; Lee, K. Y.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2002, 43, 4675-4678 https://doi.org/10.1016/S0040-4039(02)00884-5
  29. Gowrisankar, S.; Lee, K. Y.; Lee, C. G.; Kim, J. N. Tetrahedron Lett. 2004, 45, 6141-6146 https://doi.org/10.1016/j.tetlet.2004.06.057
  30. Kim, J. N.; Im, Y. J.; Gong, J. H.; Lee, K. Y. Tetrahedron Lett. 2001, 42, 4195-4197 https://doi.org/10.1016/S0040-4039(01)00687-6
  31. Im, Y. J.; Chung, Y. M.; Gong, J. H.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 787-788 https://doi.org/10.5012/bkcs.2002.23.6.787
  32. Lee, K. Y.; Gowrisankar, S.; Lee, Y. J.; Kim, J. N. Tetrahedron 2006, 62, 8798-8804 https://doi.org/10.1016/j.tet.2006.06.093
  33. Gowrisanakr, S.; Lee, H. S.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 2097-2100 https://doi.org/10.5012/bkcs.2006.27.12.2097
  34. Lee, H. S.; Kim, S. J.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 1063-1066 https://doi.org/10.5012/bkcs.2006.27.7.1063
  35. Singh, V.; Batra, S. Eur. J. Org. Chem. 2007, 2970-2976
  36. Kubo, Y.; Todani, T.; Inoue, T.; Ando, H.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1993, 66, 541-549 https://doi.org/10.1246/bcsj.66.541
  37. Bryant, R. W., Jr.; Bentley, R. Biochemistry 1976, 15, 4792-4796
  38. Bennett, M. A.; Wenger, E. Organometallics 1996, 15, 5536-5541 https://doi.org/10.1021/om9607210

Cited by

  1. Synthesis of 1-Arylnaphthalenes by Gold-Catalyzed One-Pot Sequential Epoxide to Carbonyl Rearrangement and Cyclization with Arylalkynes vol.8, pp.2, 2012, https://doi.org/10.1002/asia.201200817
  2. Active methylene compounds (AMCs) controlled facile synthesis of acridine and phenanthridine from morita Baylis–Hillman acetate vol.7, pp.86, 2017, https://doi.org/10.1039/C7RA09447G
  3. Recent advances in the Pd-catalyzed chemical transformations of Baylis-Hillman adducts vol.65, pp.43, 2009, https://doi.org/10.1016/j.tet.2009.07.034
  4. Pd(II)-Catalyzed Acetoxylation of Uracil via Electrophilic Palladation vol.31, pp.1, 2008, https://doi.org/10.5012/bkcs.2010.31.01.238
  5. Azidophosphonium salt-directed chemoselective synthesis of ( E )/( Z )-cinnamyl-1 H -triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts vol.16, pp.None, 2020, https://doi.org/10.3762/bjoc.16.130
  6. Aromaticity-Driven Access to Cycloalkyl-Fused Naphthalenes vol.23, pp.10, 2008, https://doi.org/10.1021/acs.orglett.1c01220