Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

An Efficient Synthesis of Functionalized 1,6-Dienes from Baylis-Hillman Adducts via a Pd-Catalyzed Decarboxylative Protonation Protocol

  • Park, Bo-Ram (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)
  • Received : 2010.04.04
  • Accepted : 2010.05.10
  • Published : 2010.07.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Bassindale, M. J.; Edwards, A. S.; Hamley, P.; Adams, H.; Harrity, J. P. A. Chem. Commun. 2000, 1035-1036.
  2. Pei, T.; Widenhoefer, R. A. Org. Lett. 2000, 2, 1469-1471. https://doi.org/10.1021/ol005810u
  3. Widenhoefer, R. A.; Perch, N. S. Org. Lett. 1999, 1, 1103-1105. https://doi.org/10.1021/ol9908981
  4. Nayak, M.; Batra, S. Eur. J. Org. Chem. 2009, 3505-3507.
  5. Bhar, S.; Chaudhuri, S. K.; Sahu, S. G.; Panja, C. Tetrahedron 2001, 57, 9011-9016. https://doi.org/10.1016/S0040-4020(01)00896-1
  6. Schuster, M.; Blechert, S. Angew. Chem. Int. Ed. 1997, 36, 2036-2056. https://doi.org/10.1002/anie.199720361
  7. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. https://doi.org/10.1016/S0040-4020(97)10427-6
  8. Patil, N. T.; Kadota, I.; Shibuya, A.; Gyoung, Y. S.; Yamamoto, Y. Adv. Synth. Catal. 2004, 346, 800-804. https://doi.org/10.1002/adsc.200404046
  9. Doi, T.; Hirabayashi, K.; Kokubo, M.; Komagata, T.; Yamamoto, K.; Takahashi, T. J. Org. Chem. 1996, 61, 8360-8361. https://doi.org/10.1021/jo961012z
  10. Basavaiah, D.; Reddy, R. J. Org. Biomol. Chem. 2008, 6, 1034-1039. https://doi.org/10.1039/b717843c
  11. Basavaiah, D.; Satyanarayana, T. Org. Lett. 2001, 3, 3619-3622. https://doi.org/10.1021/ol016469w
  12. 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
  13. Kim, S. J.; Lee, H. S.; Kim, J. N. Tetrahedron Lett. 2007, 48, 1069-1072. https://doi.org/10.1016/j.tetlet.2006.11.180
  14. Gan, K.-H.; Jhong, C.-J.; Yang, S.-C. Tetrahedron 2008, 64, 1204-1212. https://doi.org/10.1016/j.tet.2007.11.082
  15. Ranu, B. C.; Chattopadhyay, K.; Adak, L. Org. Lett. 2007, 9, 4595-4598. https://doi.org/10.1021/ol702099v
  16. Giambastiani, G.; Poli, G. J. Org. Chem. 1998, 63, 9608-9609. https://doi.org/10.1021/jo981599c
  17. Gowrisankar, S.; Kim, K. H.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 6241-6244. https://doi.org/10.1016/j.tetlet.2008.08.051
  18. Kim, S. H.; Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 3038-3041. https://doi.org/10.1016/j.tetlet.2009.04.006
  19. Kim, J. M.; Kim, S. H.; Lee, H. S.; Kim, J. N. Tetrahedron Lett. 2009, 50, 1734-1737. https://doi.org/10.1016/j.tetlet.2009.01.151
  20. Kim, S. H.; Kim, E. S.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 6256-6260. https://doi.org/10.1016/j.tetlet.2009.09.014
  21. Kim, K. H.; Kim, E. S.; Kim, J. N. Tetrahedron Lett. 2009, 50, 5322-5325. https://doi.org/10.1016/j.tetlet.2009.06.142
  22. Gowrisankar, S.; Lee, H. S.; Kim, S. H.; Lee, K. Y.; Kim, J. N. Tetrahedron 2009, 65, 8769-8780. https://doi.org/10.1016/j.tet.2009.07.034
  23. Gowrisankar, S.; Kim, S. H.; Kim, J. N. Bull. Korean Chem. Soc. 2009, 30, 726-728 https://doi.org/10.5012/bkcs.2009.30.3.726
  24. Basavaiah, D.; Reddy, K. R.; Kumaragurubaran, N. Nature Protocols 2007, 2, 2665-2676. https://doi.org/10.1038/nprot.2007.369
  25. Das, B.; Banerjee, J.; Ravindranath, N. Tetrahedron 2004, 60, 8357-8361. https://doi.org/10.1016/j.tet.2004.07.022
  26. Fernandes, L.; Bortoluzzi, A. J.; Sa, M. M. Tetrahedron 2004, 60, 9983-9989. https://doi.org/10.1016/j.tet.2004.08.018
  27. Sa, M. M.; Ramos, M. D.; Fernandes, L. Tetrahedron 2006, 62, 11652-11656. https://doi.org/10.1016/j.tet.2006.09.059
  28. Deng, J.; Hu, X.-P.; Huang, J.-D.; Yu, S.-B.; Wang, D.-Y.; Duan, Z.-C.; Zheng, Z. J. Org. Chem. 2008, 73, 2015-2017. https://doi.org/10.1021/jo702510m
  29. Lee, K. Y.; Lee, Y. J.; Kim, J. N. Bull. Korean Chem. Soc. 2007, 28, 143-146. https://doi.org/10.5012/bkcs.2007.28.1.143
  30. Lee, K. Y.; Park, D. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 1489-1492. https://doi.org/10.5012/bkcs.2006.27.9.1489
  31. Tsuji, J.; Nisar, M.; Shimizu, I. J. Org. Chem. 1985, 50, 3416-3417. https://doi.org/10.1021/jo00218a037
  32. Mandai, T.; Imaji, M.; Takada, H.; Kawata, M.; Nokami, J.; Tsuji, J. J. Org. Chem. 1989, 54, 5395-5397. https://doi.org/10.1021/jo00283a044
  33. Tsuji, J. Pure Appl. Chem. 1986, 58, 869-878. https://doi.org/10.1351/pac198658060869
  34. Marinescu, S. C.; Nishimata, T.; Mohr, J. T.; Stoltz, B. M. Org. Lett. 2008, 10, 1039-1042. https://doi.org/10.1021/ol702821j
  35. Ragoussis, V.; Giannikopoulos, A. Tetrahedron Lett. 2006, 47, 683-687. https://doi.org/10.1016/j.tetlet.2005.11.122
  36. Tsuji, J.; Yamada, T.; Minami, I.; Yuhara, M.; Nisar, M.; Shimizu, I. J. Org. Chem. 1987, 52, 2988-2995. https://doi.org/10.1021/jo00390a007
  37. Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 4138-4139. https://doi.org/10.1021/ja070116w
  38. Waetzig, S. R.; Rayabarapu, D. K.; Weaver, J. D.; Tunge, J. A. Angew. Chem. Int. Ed. 2006, 45, 4977-4980. https://doi.org/10.1002/anie.200600721
  39. Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 14860-14861. https://doi.org/10.1021/ja077070r
  40. You, S.-L.; Dai, L.-X. Angew. Chem. Int. Ed. 2006, 45, 5246-5248. https://doi.org/10.1002/anie.200601889
  41. Imao, D.; Itoi, A.; Yamazaki, A.; Shirakura, M.; Ohtoshi, R.; Ogata, K.; Ohmori, Y.; Ohta, T.; Ito, Y. J. Org. Chem. 2007, 72, 1652-1658. https://doi.org/10.1021/jo0621569
  42. Nakamura, M.; Hajra, A.; Endo, K.; Nakamura, E. Angew. Chem. Int. Ed. 2005, 44, 7248-7251. https://doi.org/10.1002/anie.200502703
  43. Mohr, J. T.; Behenna, D. C.; Harned, A. M.; Stoltz, B. M. Angew. Chem. Int. Ed. 2005, 44, 6924-6927. https://doi.org/10.1002/anie.200502018

Cited by

  1. Palladium-Catalyzed Coupling of Alkynes with Unactivated Alkenes in Ionic Liquids: A Regio- and Stereoselective Synthesis of Functionalized 1,6-Dienes and Their Analogues vol.78, pp.24, 2013, https://doi.org/10.1021/jo402159d