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Korean Chemical Society (대한화학회)
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Palladium-Catalyzed Domino Heck-Cyanation Cascade to 3-Cyanomethyl 2,3-Dihydrobenzofuran and 2,3-Dihydroindoles

  • Lee, Hyun-Seung (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) ;
  • Lim, Jin-Woo (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 : 2010.12.27
  • Accepted : 2011.01.17
  • Published : 2011.03.20
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References

  1. de Meijere, A.; Brase, S. J. Organomet. Chem. 1999, 576, 88-110. https://doi.org/10.1016/S0022-328X(98)01087-0
  2. de Meijere, A.; Meyer, F. E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
  3. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644-4680. https://doi.org/10.1021/cr0683966
  4. Hu, Y.; Yu, C.; Ren, D.; Hu, Q.; Zhang, L.; Cheng, D. Angew. Chem. Int. Ed. 2009, 48, 5448-5451. https://doi.org/10.1002/anie.200901246
  5. Trost, B. M.; O'Boyle, B. M.; Hund, D. Chem. Eur. J. 2010, 16, 9772-9776. https://doi.org/10.1002/chem.201001689
  6. Kim, E. S.; Kim, K. H.; Park, S.; Kim, J. N. Tetrahedron Lett. 2010, 51, 4648-4652. https://doi.org/10.1016/j.tetlet.2010.06.127
  7. de Meijere, A.; von Zezschwitz, P.; Brase, S. Acc. Chem. Res. 2005, 38, 413-422. https://doi.org/10.1021/ar980025r
  8. Negishi, E.-I.; Coperet, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365-393. https://doi.org/10.1021/cr950020x
  9. Schweizer, S.; Song, Z.-Z.; Meyer, F. E.; Parsons, P. J.; de Meijere, A. Angew. Chem. Int. Ed. 1999, 38, 1452-1454. https://doi.org/10.1002/(SICI)1521-3773(19990517)38:10<1452::AID-ANIE1452>3.0.CO;2-P
  10. Schweizer, S.; Tokan, W. M.; Parsons, P. J.; de Meijere, A. Eur. J. Org. Chem. 2010, 4687-4699.
  11. Hu, Y.; Ouyang, Y.; Qu, Y.; Hu, Q.; Yao, H. Chem. Commun. 2009, 4575-4577.
  12. Taniguchi, T.; Zaimoku, H.; Ishibashi, H. J. Org. Chem. 2009, 74, 2624-2626. https://doi.org/10.1021/jo802787j
  13. Grigg, R.; Sakee, U.; Sridharan, V.; Sukirthalingam, S.; Thangavelauthum, R. Tetrahedron 2006, 62, 9523-9532. https://doi.org/10.1016/j.tet.2006.07.100
  14. 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
  15. Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 7460-7461. https://doi.org/10.1021/ja047980y
  16. Ruck, R. T.; Huffman, M. A.; Kim, M. M.; Shevlin, M.; Kandur, W. V.; Davies, I. W. Angew. Chem. Int. Ed. 2008, 47, 4711-4714. https://doi.org/10.1002/anie.200800549
  17. Brown, D.; Grigg, R.; Sridharan, V.; Tambyrajah, V. Tetrahedron Lett. 1995, 36, 8137-8140. https://doi.org/10.1016/0040-4039(95)01696-F
  18. Jana, R.; Samanta, S.; Ray, J. K. Tetrahedron Lett. 2008, 49, 851-854. https://doi.org/10.1016/j.tetlet.2007.11.172
  19. Liron, F.; Knochel, P. Tetrahedron Lett. 2007, 48, 4943-4946. https://doi.org/10.1016/j.tetlet.2007.05.018
  20. 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
  21. Kim, S. H.; Lee, H. S.; Kim, K. H.; Kim, J. N. Tetrahedron Lett. 2010, 51, 4267-4271. https://doi.org/10.1016/j.tetlet.2010.06.046
  22. Liu, P.; Huang, L.; Lu, Y.; Dilmeghani, M.; Baum, J.; Xiang, T.; Adams, J.; Tasker, A.; Larsen, R.; Faul, M. M. Tetrahedron Lett. 2007, 48, 2307-2310. https://doi.org/10.1016/j.tetlet.2007.01.156
  23. Szlosek-Pinaud, M.; Diaz, P.; Martinez, J.; Lamaty, F. Tetrahedron 2007, 63, 3340-3349. https://doi.org/10.1016/j.tet.2007.02.035
  24. Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam, S.; Wilson, D.; Redpath, J. Tetrahedron 2000, 56, 7525-7539. https://doi.org/10.1016/S0040-4020(00)00659-1
  25. Grigg, R.; Kilner, C.; Mariani, E.; Sridharan, V. Synlett 2006, 3021-3024.
  26. Grigg, R.; Inman, M.; Kilner, C.; Koppen, I.; Marchbank, J.; Selby, P.; Sridharan, V. Tetrahedron 2007, 63, 6152-6169. https://doi.org/10.1016/j.tet.2007.03.044
  27. Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65-87 and further references cited therein. https://doi.org/10.1016/S0022-328X(98)01052-3
  28. Pinto, A.; Jia, Y.; Neuville, L.; Zhu, J. Chem. Eur. J. 2007, 13, 961-967. https://doi.org/10.1002/chem.200601016
  29. Jaegli, S.; Vors, J.-P.; Neuville, L.; Zhu, J. Synlett 2009, 2997-2999.
  30. Lu, Z.; Hu, C.; Guo, J.; Li, J.; Cui, Y.; Jia, Y. Org. Lett. 2010, 12, 480-483. https://doi.org/10.1021/ol902672a
  31. Cheng, Y.; Duan, Z.; Yu, L.; Li, Z.; Zhu, Y.; Wu, Y. Org. Lett. 2008, 10, 901-904. https://doi.org/10.1021/ol703018t
  32. Huang, Q.; Larock, R. C. Tetrahedron Lett. 2009, 50, 7235-7238. https://doi.org/10.1016/j.tetlet.2009.10.013
  33. Nandi, S.; Ray, J. K. Tetrahedron Lett. 2009, 50, 6993-6997. https://doi.org/10.1016/j.tetlet.2009.09.156
  34. Rene, O.; Lapointe, D.; Fagnou, K. Org. Lett. 2009, 11, 4560-4563. https://doi.org/10.1021/ol901799p
  35. Nandi, S.; Samanta, S.; Jana, S.; Ray, J. K. Tetrahedron Lett. 2010, 51, 5294-5297. https://doi.org/10.1016/j.tetlet.2010.07.162
  36. Zhang, Y.; Lee, Y. S.; Rothman, R. B.; Dersch, C. M.; Deschamps, J. R.; Jacobson, A. E.; Rice, K. C. J. Med. Chem. 2009, 52, 7570-7579. https://doi.org/10.1021/jm9004225
  37. Iyer, M. R.; Lee, Y. S.; Deschamps, J. R.; Rothman, R. B.; Dersch, C. M.; Jacobson, A. E.; Rice, K. C. Bioorg. Med. Chem. 2010, 18, 91-99. https://doi.org/10.1016/j.bmc.2009.11.022
  38. Trost, B. M.; Tang, W. Angew. Chem. Int. Ed. 2002, 41, 2795-2797. https://doi.org/10.1002/1521-3773(20020802)41:15<2795::AID-ANIE2795>3.0.CO;2-2
  39. Trost, B. M.; Tang, W.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 14785-14803. https://doi.org/10.1021/ja054449+
  40. Meijs, G. F.; Beckwith, A. L. J. J. Am. Chem. Soc. 1986, 108, 5890-5893. https://doi.org/10.1021/ja00279a038
  41. Nakao, Y.; Ebata, S.; Yada, A.; Hiyama, T.; Ikawa, M.; Ogoshi, S. J. Am. Chem. Soc. 2008, 130, 12874-12875. https://doi.org/10.1021/ja805088r
  42. Hsieh, J.-C.; Ebata, S.; Nakao, Y.; Hiyama, T. Synlett 2010, 1709-1711.
  43. Liu, K. G.; Lo, J. R.; Robichaud, A. J. Tetrahedron 2010, 66, 573-577 and further references cited therein. https://doi.org/10.1016/j.tet.2009.11.080
  44. Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; Wiley and Sons: New York, 2003; pp 431-517.
  45. Kim, H. S.; Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 3154-3157. https://doi.org/10.1016/j.tetlet.2008.11.127

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