DOI QR코드

DOI QR Code

Pd-Mediated Cross-Coupling Reactions between the Bromide of Baylis-Hillman Adduct and Organostannanes

  • Gowrisankar, Saravanan (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Sung-Hwan (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science)
  • Published : 2009.03.20

Abstract

Keywords

References

  1. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891 https://doi.org/10.1021/cr010043d
  2. Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 51, pp 201-350
  3. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001-8062 https://doi.org/10.1016/0040-4020(96)00154-8
  4. Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627-645 https://doi.org/10.2174/1385272023374094
  5. 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
  6. Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511-4574 https://doi.org/10.1016/j.tet.2008.02.087
  7. Srihari, P.; Singh, A. P.; Basak, A. K.; Yadav, J. S. Tetrahedron Lett. 2007, 48, 5999-6001 https://doi.org/10.1016/j.tetlet.2007.06.120
  8. Yadav, J. S.; Reddy, B. V. S.; Mandal, S. S.; Singh, A. P.; Basak, A. K. Synthesis 2008, 1943-1947
  9. Yadav, J. S.; Reddy, B. V. S.; Singh, A. P.; Basak, A. K. Synthesis 2008, 469-473
  10. Mandal, S. K.; Paira, M.; Roy, S. C. J. Org. Chem. 2008, 73, 3823-3827 https://doi.org/10.1021/jo800049p
  11. Gowrisankar, S.; Lee, C. G.; Kim, J. N. Tetrahedron Lett. 2004, 45, 6949-6953 https://doi.org/10.1016/j.tetlet.2004.07.070
  12. Ranu, B. C.; Chattopadhyay, K.; Jana, R. Tetrahedron Lett. 2007, 48, 3847-3850 https://doi.org/10.1016/j.tetlet.2007.03.154
  13. Basavaiah, D.; Pandiaraju, S.; Padmaja, K. Synlett 1996, 393-395
  14. Basavaiah, D.; Krishnamacharyulu, M.; Hyma, R. S.; Pandiaraju, S. Tetrahedron Lett. 1997, 38, 2141-2144 https://doi.org/10.1016/S0040-4039(97)00266-9
  15. Lee, H. J.; Seong, M. R.; Kim, J. N. Tetrahedron Lett. 1998, 39, 6223-6226 https://doi.org/10.1016/S0040-4039(98)01280-5
  16. Das, B.; Majhi, A.; Banerjee, J.; Chowdhury, N.; Venkateswarlu, K. Chem. Lett. 2005, 34, 1492-1493 https://doi.org/10.1246/cl.2005.1492
  17. Shanmugam, P.; Rajasingh, P. Chem. Lett. 2005, 34, 1494-1495 https://doi.org/10.1246/cl.2005.1494
  18. Kabalka, G. W.; Dong, G.; Venkataiah, B.; Chen, C. J. Org. Chem. 2005, 70, 9207-9210 https://doi.org/10.1021/jo051177k
  19. Kabalka, G. W.; Venkataiah, B.; Dong, G. Org. Lett. 2003, 5, 3803-3805 https://doi.org/10.1021/ol0351798
  20. Navarre, L.; Darses, S.; Genet, J.-P. Chem. Commun. 2004, 1108-1109
  21. Navarre, L.; Darses, S.; Genet, J.-P. Adv. Synth. Catal. 2006, 348, 317-322 https://doi.org/10.1002/adsc.200505336
  22. Kantam, M. L.; Kumar, K. B. S.; Sreedhar, B. J. Org. Chem. 2008, 73, 320-322 https://doi.org/10.1021/jo701982m
  23. 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
  24. 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
  25. 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
  26. 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
  27. 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
  28. 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
  29. Godschalx, J.; Stille, J. K. Tetrahedron Lett. 1980, 21, 2599-2602 https://doi.org/10.1016/S0040-4039(00)92815-6
  30. Trost, B. M.; Keinan, E. Tetrahedron Lett. 1980, 21, 2595-2598 https://doi.org/10.1016/S0040-4039(00)92814-4
  31. Trost, B. M.; Pietrusiewicz, K. M. Tetrahedron Lett. 1985, 26, 4039-4042 https://doi.org/10.1016/S0040-4039(00)89287-4
  32. Mendez, M.; Cuerva, J. M.; Gomez-Bengoa, E.; Cardenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2002, 8, 3620-3628 https://doi.org/10.1002/1521-3765(20020816)8:16<3620::AID-CHEM3620>3.0.CO;2-P
  33. Das, B.; Banerjee, J.; Ravindranath, N. Tetrahedron 2004, 60, 8357-8361 https://doi.org/10.1016/j.tet.2004.07.022
  34. Fernandes, L.; Bortoluzzi, A. J.; Sa, M. M. Tetrahedron 2004, 60, 9983-9989 https://doi.org/10.1016/j.tet.2004.08.018
  35. Sa, M. M.; Ramos, M. D.; Fernandes, L. Tetrahedron 2006, 62, 11652-11656 https://doi.org/10.1016/j.tet.2006.09.059
  36. 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
  37. Buchholz, R.; Hoffmann, H.; Martin, R. Helv. Chim. Acta 1991, 74, 1213-1220 https://doi.org/10.1002/hlca.19910740608
  38. Mazdiyasni, H.; Konopacki, D. B.; Dickman, D. A.; Zydowsky, T. M. Tetrahedron Lett. 1993, 34, 435-438 https://doi.org/10.1016/0040-4039(93)85095-E
  39. Basavaiah, D.; Reddy, K. R.; Kumaragurubaran, N. Nature Protocols 2007, 2, 2665-2676 https://doi.org/10.1038/nprot.2007.369
  40. 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
  41. 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
  42. Basavaiah, D.; Kumaragurubaran, N.; Padmaja, K. Synlett 1999, 1630-1632
  43. Deng, B.-L.; Lepoivre, J. A.; Lemiere, G. Eur. J. Org. Chem. 1999, 2683-2688
  44. Murata, M.; Watanabe, S.; Masuda, Y. Synlett 2000, 1043-1045
  45. Richter, F.; Weichmann, H. J. Organometal. Chem. 1994, 466, 77-87 https://doi.org/10.1016/0022-328X(94)88031-X
  46. Fouquet, E.; Pereyre, M.; Rodriguez, A. L.; Roulet, T. Bull. Soc. Chim. Fr. 1997, 134, 959-967
  47. Burnett, D. A.; Caplen, M. A.; Domalski, M. S.; Browne, M. E.; Davis, H. R., Jr.; Clader, J. W. Bioorg. Med. Chem. Lett. 2002, 12, 311-314 https://doi.org/10.1016/S0960-894X(01)00750-8
  48. Hervet, M.; Thery, I.; Gueiffier, A.; Enguehard-Gueiffier, C. Helv. Chim. Acta 2003, 86, 3461-3469 https://doi.org/10.1002/hlca.200390290
  49. Li, J.; Qian, W.; Zhang, Y. Tetrahedron 2004, 60, 5793-5798 https://doi.org/10.1016/j.tet.2004.04.087
  50. Thibonnet, J.; Vu, V. A.; Berillon, L.; Knochel, P. Tetrahedron 2002, 58, 4787-4799 https://doi.org/10.1016/S0040-4020(02)00439-8
  51. Thibonnet, J.; Knochel, P. Tetrahedron Lett. 2000, 41, 3319-3322 https://doi.org/10.1016/S0040-4039(00)00387-7

Cited by

  1. Synthesis of Poly-Substituted Benzene Derivatives via [3+3] Annulation Protocol from Morita-Baylis-Hillman Adducts and Glutaconates vol.34, pp.11, 2013, https://doi.org/10.5012/bkcs.2013.34.11.3503
  2. An Expedient Synthesis of Cinnamyl Fluorides from Morita-Baylis-Hillman Adducts vol.34, pp.3, 2013, https://doi.org/10.5012/bkcs.2013.34.3.993
  3. ChemInform Abstract: Pd-Mediated Cross-Coupling Reactions Betwen the Bromide of Baylis-Hillman Adduct and Organostannanes. vol.40, pp.32, 2009, https://doi.org/10.1002/chin.200932061
  4. 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
  5. Pd(II)-Catalyzed Acetoxylation of Uracil via Electrophilic Palladation vol.31, pp.1, 2009, https://doi.org/10.5012/bkcs.2010.31.01.238
  6. An Efficient Synthesis of Functionalized 1,6-Dienes from Baylis-Hillman Adducts via a Pd-Catalyzed Decarboxylative Protonation Protocol vol.31, pp.7, 2009, https://doi.org/10.5012/bkcs.2010.31.7.2057
  7. An Efficient Synthesis of Phospha-Morita-Baylis-Hillman Adducts via Michaelis-Arbuzov Reaction of the DABCO Salt of Morita-Baylis-Hillman Bromide vol.34, pp.1, 2009, https://doi.org/10.5012/bkcs.2013.34.1.133