Bulletin of the Korean Chemical Society

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Palladium-catalyzed Carbonylative Cyclization of 2-Bromocyclohex-1-enecarbaldehydes with Aliphatic Primary Amines Leading to 3-Aminohydroisoindol-1-ones

  • Bae, Yeon Kyu (Department of Applied Chemistry, Kyungpook National University) ;
  • Cho, Chan Sik (Department of Applied Chemistry, Kyungpook National University) ;
  • Yoon, Nam Sik (Department of Textile System Engineering, Kyungpook National University)
  • Received : 2013.04.25
  • Accepted : 2013.06.02
  • Published : 2013.09.20
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Abstract

Keywords

References

  1. Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds; Plenum Press: New York, 1991.
  2. Tsuji, J. Palladium Reagents and Catalysis; Wiley: Chichester, 1995.
  3. El Ali, B.; Alper, H. Synlett 2000, 161.
  4. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002; Vol. 2.
  5. Modern Carbonylation Methods; Kollar, L., Ed.; Wiley-VCH: Weinheim, 2008.
  6. Brennfuhrer, A.; Neumann, H.; Beller, M. Angew. Chem. Int. Ed. 2009, 48, 4114. https://doi.org/10.1002/anie.200900013
  7. Grigg, R.; Mutton, S. P. Tetrahedron 2010, 66, 5515. https://doi.org/10.1016/j.tet.2010.03.090
  8. Cho, C. S.; Patel, D. B.; Shim, S. C. Tetrahedron 2005, 61, 9490. https://doi.org/10.1016/j.tet.2005.08.001
  9. Cho, C. S.; Patel, D. B. Tetrahedron 2006, 62, 6388. https://doi.org/10.1016/j.tet.2006.04.031
  10. Cho, C. S.; Kim, H. B.; Ren, W. X.; Yoon, N. S. Appl. Organomet. Chem. 2010, 24, 817. https://doi.org/10.1002/aoc.1709
  11. Cho, C. S.; Kim, H. B. J. Organomet. Chem. 2011, 696, 3264. https://doi.org/10.1016/j.jorganchem.2011.06.044
  12. Cho, C. S.; Son, J. I.; Yoon, N. S. Appl. Organomet. Chem. 2012, 26, 499. https://doi.org/10.1002/aoc.2887
  13. Arnold, Z.; Holly, A. Collect. Czech. Chem. Commun. 1961, 26, 3059. https://doi.org/10.1135/cccc19613059
  14. Coates, R. M.; Senter, P. D.; Baker, W. R. J. Org. Chem. 1982, 47, 3597. https://doi.org/10.1021/jo00140a001
  15. Brahma, S.; Ray, J. K. Tetrahedron 2008, 64, 2883. https://doi.org/10.1016/j.tet.2007.11.112
  16. Ray, J. K.; Haldar, M. K.; Gupta, S.; Kar, G. K. Tetrahedron 2000, 56, 909. https://doi.org/10.1016/S0040-4020(99)01080-7
  17. Zhang, Y.; Herndon, J. W. Org. Lett. 2003, 5, 2043. https://doi.org/10.1021/ol034414j
  18. Banwell, M. G.; Kelly, B. D.; Kokas, O. J.; Lupton, D. W. Org. Lett. 2003, 5, 2497. https://doi.org/10.1021/ol034745w
  19. Banwell, M. G.; Lupton, D. W.; Ma, X.; Renner, J.; Sydnes, M. O. Org. Lett. 2004, 6, 2741. https://doi.org/10.1021/ol0490375
  20. Mal, S. K.; Ray, D.; Ray, J. K. Tetrahedron Lett. 2004, 45, 277.
  21. Ray, D.; Mal, S. K.; Ray, J. K. Synlett 2005, 2135.
  22. Some, S.; Dutta, B.; Ray, J. K. Tetrahedron Lett. 2006, 47, 1221. https://doi.org/10.1016/j.tetlet.2005.11.146
  23. Ray, D.; Ray, J. K. Tetrahedron Lett. 2007, 48, 673. https://doi.org/10.1016/j.tetlet.2006.11.104
  24. Some, S.; Ray, J. K.; Banwell, M. G.; Jones, M. T. Tetrahedron Lett. 2007, 48, 3609. https://doi.org/10.1016/j.tetlet.2007.03.078
  25. Some, S.; Ray, J. K. Tetrahedron Lett. 2007, 48, 5013. https://doi.org/10.1016/j.tetlet.2007.05.111
  26. Ray, D.; Paul, S.; Brahma, S.; Ray, J. K. Tetrahedron Lett. 2007, 48, 8005. https://doi.org/10.1016/j.tetlet.2007.09.052
  27. Ray, D.; Ray, J. K. Org. Lett. 2007, 9, 191. https://doi.org/10.1021/ol062418t
  28. Jana, R.; Samanta, S.; Ray, J. K. Tetrahedron Lett. 2008, 49, 851. https://doi.org/10.1016/j.tetlet.2007.11.172
  29. Jana, R.; Chatterjee, I.; Samanta, S.; Ray, J. K. Org. Lett. 2008, 10, 4795. https://doi.org/10.1021/ol801882t
  30. Karthikeyan, P.; Meena Rani, A.; Saiganesh, R.; Balasubramanian, K. K.; Kabilan, S. Tetrahedron 2009, 65, 811. https://doi.org/10.1016/j.tet.2008.11.049
  31. Samanta, S.; Jana, R.; Ray, J. K. Tetrahedron Lett. 2009, 50, 6751. https://doi.org/10.1016/j.tetlet.2009.09.071
  32. Nandi, S.; Ray, J. K. Tetrahedron Lett. 2009, 50, 6993. https://doi.org/10.1016/j.tetlet.2009.09.156
  33. Jana, R.; Paul, S.; Biswas, A.; Ray, J. K. Tetrahedron Lett. 2010, 51, 273. https://doi.org/10.1016/j.tetlet.2009.10.125
  34. Samanta, S.; Yasmin, N.; Kundu, D.; Ray, J. K. Tetrahedron Lett. 2010, 51, 4132. https://doi.org/10.1016/j.tetlet.2010.05.142
  35. Yasmin, N.; Ray, J. K. Synlett 2010, 924.
  36. Yasmin, N.; Ray, J. K. Tetrahedron Lett. 2010, 51, 4759.
  37. Paul, S.; Gorai, T.; Koley, A.; Ray, J. K. Tetrahedron Lett. 2011, 52, 4051. https://doi.org/10.1016/j.tetlet.2011.05.148
  38. Cho, C. S.; Shim, H. S. Tetrahedron Lett. 2006, 47, 3835. https://doi.org/10.1016/j.tetlet.2006.03.184
  39. Cho, C. S.; Kim, J. U.; Choi, H.-J. J. Organomet. Chem. 2008, 693, 3677. https://doi.org/10.1016/j.jorganchem.2008.09.014
  40. Cho, C. S.; Kim, H. B.; Lee, S. Y. J. Organomet. Chem. 2010, 695, 1744. https://doi.org/10.1016/j.jorganchem.2010.03.025
  41. Cho, C. S.; Kim, H. B. Catal. Lett. 2010, 140, 116. https://doi.org/10.1007/s10562-010-0457-2
  42. Lee, H. K.; Cho, C. S. Appl. Organomet. Chem. 2012, 26, 185. https://doi.org/10.1002/aoc.2836
  43. Lee, H. K.; Cho, C. S. Appl. Organomet. Chem. 2012, 26, 406. https://doi.org/10.1002/aoc.2864
  44. Lee, H. K.; Cho, C. S. Appl. Organomet. Chem. 2012, 26, 570. https://doi.org/10.1002/aoc.2900
  45. Cho, C. S.; Ren, W. X. Tetrahedron Lett. 2009, 50, 2097. https://doi.org/10.1016/j.tetlet.2009.02.109
  46. Schreiner, S.; Yu, J. Y.; Vaska, L. J. Chem. Soc., Chem. Commun. 1988, 602.
  47. Yu, J. Y.; Schreiner, S.; Vaska, L. Inorg. Chim. Acta 1990, 170, 145. https://doi.org/10.1016/S0020-1693(00)80465-X
  48. Schumacher, N.; Boisen, A.; Dahl, S.; Gokhale, A. A.; Kandoi, S.; Grabow, L. C.; Dumesic, J. A.; Mavrikakis, M.; Chorkendorff, I. J. Catal. 2005, 229, 265. https://doi.org/10.1016/j.jcat.2004.10.025
  49. Takaya, J.; Sangu, K.; Iwasawa, N. Angew. Chem. Int. Ed. 2009, 48, 7090. https://doi.org/10.1002/anie.200902884
  50. Cho, C. S.; Lee, J. W.; Lee, D. Y.; Shim, S. C.; Kim, T. J. Chem. Commun. 1996, 2115.
  51. Cho, C. S.; Chu, D. Y.; Lee, D. Y.; Shim, S. C.; Kim, T.-J.; Lim, W. T.; Heo, N. H. Synth. Commun. 1997, 27, 4141. https://doi.org/10.1080/00397919708005462
  52. Cho, C. S.; Jiang, L. H.; Lee, D. Y.; Shim, S. C.; Lee, H. S.; Cho, S.-D. J. Heterocyclic Chem. 1997, 34, 1371. https://doi.org/10.1002/jhet.5570340446
  53. Cho, C. S.; Jiang, L. H.; Shim, S. C. Synth. Commun. 1998, 28, 849. https://doi.org/10.1080/00032719808006483
  54. Nikitin, K. V.; Andryukhova, N. P. Synthesis 2001, 89

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