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The Functionalization of Six Membered Rings

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Heterocycles from Transition Metal Catalysis

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 28))

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7.5 References

  1. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Stanforth, S. S. Tetrahedron 1998, 54, 263. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.

    Article  CAS  Google Scholar 

  2. For a recent review on heterocyclic boronic acids see Tyrrel, E.; Brookes, P. Synthesis, 2003, 469.

    Google Scholar 

  3. Zoltewicz, J. A.; Cruskie, M. P., Jr. Tetrahedron 1995, 51, 11393.

    Article  CAS  Google Scholar 

  4. Li, J. J.; Yue, W. S. Tetrahedron Letters 1999, 40, 4507.

    CAS  Google Scholar 

  5. (a) Ishikura, M.; Kamada, M.; Terashima, M. Heterocycles 1984, 22, 265. (b) Ishikura, M.; Kamada, M.; Terashima, M. Synthesis 1984, 936.

    Article  CAS  Google Scholar 

  6. Deshayes, K.; Broene, R. D.; Chao, I.; Knobler, C. B.; Diederich, F. D. J. Org. Chem. 1991, 56, 6787.

    Article  CAS  Google Scholar 

  7. Parry, P. R.; Changsheng, W.; Batsanov, A. S.; Bryce, M. R.; Tarbit, B. J. Org. Chem. 2002, 67, 7541.

    Article  CAS  Google Scholar 

  8. Ishikura, M.; Oda, I.; Terashima, M. Heterocycles 1985, 23, 2375.

    CAS  Google Scholar 

  9. Ishiyama, T.; Ishida, K.; Miyaura, N. Tetrahedron, 2001, 57, 9813.

    Article  CAS  Google Scholar 

  10. Fuller, A. A.; Hester, H. R.; Salo, E. V.; Stevens, E. P. Tetrahedron Lett. 2003, 44, 2935.

    Article  CAS  Google Scholar 

  11. Csányi, D.; Timári, G. Hajós, Gy. Synth. Commun. 1999, 29, 3959.

    Google Scholar 

  12. Li, G. J. J. Org. Chem. 2002, 67, 3643 and references therein.

    CAS  Google Scholar 

  13. Yang, W.; Wang, Y.; Corte, J. R. Org. Lett. 2003, 5, 3131.

    CAS  Google Scholar 

  14. Schultheiss, N.; Bosch, E. Heterocycles 2003, 60, 1891.

    CAS  Google Scholar 

  15. Bourotte, M.; Pellegrini, N.; Schmitt, M.; Bourguignon, J-J. Synlett, 2003, 1482.

    Google Scholar 

  16. Krajsovszky, G.; Mátyus, P.; Riedl, Zs.; Csányi, D.; Hajós, Gy. Heterocycles 2001, 58, 1105.

    Google Scholar 

  17. Gronowitz, S.; Hoernfeldt, A. B.; Kristjansson, V.; Musil, T. Chemica Scripta 1986, 26, 305.

    CAS  Google Scholar 

  18. Piettre, S. R.; Andre, C.; Chanal, M-C.; Ducep, J-B.; Lesur, B.; Piriou, F.; Raboisson, P.; Rondeau, J-M.; Schelcher, C.; Zimmermann, P.; Ganzhorn, A. J. J. Med. Chem. 1997, 40, 4208.

    Article  CAS  Google Scholar 

  19. Wellmar, U.; Hörnfeldt, A.-B.; Gronowitz, S. J. Heterocycl. Chem. 1995, 32, 1159.

    CAS  Google Scholar 

  20. Kusturin, C.; Liebeskind, L. S.; Rahman, H.; Sample, K.; Schweitzer, B.; Srogl, J.; Neumann, W. L. Org. Lett. 2003, 5, 4349.

    Article  CAS  Google Scholar 

  21. Morris, G. A.; Nguyen, SB. T. Tetrahedron Lett. 2001, 42, 2093.

    CAS  Google Scholar 

  22. Stanforth, S. P. Tetrahedron 1998, 54, 263 and references therein.

    Article  CAS  Google Scholar 

  23. Böhm, V. P. W.; Weskamp, T.; Gstöttmayr, C. W. K.; Herrmann, W. A. Angew. Chem. Int. Ed. 2000, 39, 1602.

    Google Scholar 

  24. Mongin, F.; Mojovic, L.; Guillamet, B.; Trécourt, F.; Quéguiner, G. J. Org. Chem. 2002, 67, 8991.

    CAS  Google Scholar 

  25. Korn, T. J.; Cahiez, G.; Knochel, P. Synlett 2003, 1892.

    Google Scholar 

  26. Anctil, E. J-G.; Snieckus, V. J. Organomet. Chem. 2002, 653, 150.

    Article  CAS  Google Scholar 

  27. Fang, Y-Q.; Hanan, G. S. Synlett 2003, 852.

    Google Scholar 

  28. Lutzen, A.; Hapke, M.; Eur. J. Org. Chem. 2002, 2292.

    Google Scholar 

  29. Stanetty, P.; Schnürch, M.; Mihovilovic, M. D. Synlett 2003, 1862.

    Google Scholar 

  30. Mongin, F.; Trécourt, F.; Gervais, B.; Mongin, O.; Quéguiner, G. J. Org. Chem. 2002, 67, 3272.

    CAS  Google Scholar 

  31. Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343.

    Article  CAS  Google Scholar 

  32. Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077.

    CAS  Google Scholar 

  33. For an example, 2-tributylstannylpyridine see Peters, D.; Hörnfeldt, A.-B.; Gronowitz, S. J. Heterocycl. Chem. 1990, 27, 2165.

    CAS  Google Scholar 

  34. For a representative example see Benaglia, M; Ponzini, F.; Woods, C. R.; Siegel, J. S. Org. Lett. 2001, 3, 967.

    Article  CAS  Google Scholar 

  35. Schwab, P. F.; Fleischer, F.; Michl, J. J. Org. Chem. 2002, 67, 443.

    CAS  Google Scholar 

  36. Heller, M.; Schubert, U. S. J. Org. Chem. 2002, 67, 8269.

    CAS  Google Scholar 

  37. Peters, D.; Hörnfeldt, A.-B.; Gronowitz, S. J. Heterocycl. Chem. 1990, 27, 2165.

    CAS  Google Scholar 

  38. Yamamoto, Y.; Tanaka, T.; Yagi, M.; Inamoto, M. Heterocycles, 1996, 42, 189.

    CAS  Google Scholar 

  39. Takahashi, T.; Koga, H.; Sato, H.; Ishizawa, T.; Taka, N. Heterocycles, 1995, 41, 2405.

    CAS  Google Scholar 

  40. Barros, M. T.; Maycock, C. D.; Ventura, M. R. Tetrahedron Lett. 1999, 40, 557.

    CAS  Google Scholar 

  41. Kennedy, G.; Perboni, A. D. Tetrahedron Lett. 1996, 37, 7611.

    CAS  Google Scholar 

  42. Le Floch, P.; Carmichael, D.; Ricard, L.; Mathey, F. J. Am. Chem. Soc. 1993, 115, 10665.

    Google Scholar 

  43. (a) Minn, K. Synlett 1991, 115. (b) Ames, D. E.; Bull, D.; Takunda, C. Synthesis 1981, 364.

    Google Scholar 

  44. Louërat, F.; Gros, P.; Fort, Y. Tetrahedron Lett. 2003, 44, 5613.

    Google Scholar 

  45. Erdélyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165.

    Google Scholar 

  46. Kim, C.-S.; Russel, K. C. J. Org. Chem. 1998, 63, 8229.

    CAS  Google Scholar 

  47. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Higihara, N. Synthesis 1980, 627.

    Google Scholar 

  48. (a) Novák, Z.; Nemes, P.; Kotschy, A. Org. Lett. 2004, 6, 4917. (b) For a review on domino Sonogashira coupling see Nagy, A.; Novák, Z.; Kotschy, A. J. Organomet. Chem. 2005, in press.

    Google Scholar 

  49. Novák, Z.; Szabó, A.; Répási, J.; Kotschy, A. J. Org. Chem. 2003, 68, 3327.

    Google Scholar 

  50. Mori, Y.; Seki, M. J. Org. Chem. 2003, 68, 1571.

    CAS  Google Scholar 

  51. Akita, Y.; Ohta, A. Heterocycles 1982, 19, 329.

    CAS  Google Scholar 

  52. Edo, K.; Sakamoto, T.; Yamanaka, H. Chem. Pharm. Bull. 1978, 26, 3843.

    CAS  Google Scholar 

  53. Napoletano, M.; Norcini, G.; Pellacini, F.; Marchini, F.; Morazzoni, G.; Ferlenga, P.; Pradella, L. Bioorganic & Medicinal Chemistry Letters 2001, 11, 33.

    Article  CAS  Google Scholar 

  54. Novák, Z.; Kotschy, A. Org. Lett. 2003, 5, 3495.

    Google Scholar 

  55. Faragó, J.; Novák, Z.; Schlosser, G.; Csámpai, A.; Kotschy, A. Tetrahedron, 2004, 60, 1991.

    Google Scholar 

  56. Samaritani, S.; Menicagli, R. Tetrahedron 2002, 58, 1381.

    Article  CAS  Google Scholar 

  57. Sonoda, M.; Inaba, A.; Itahashi, K.; Tobe, Y. Org. Lett. 2001, 2, 2419.

    Google Scholar 

  58. Pauvert, M.; Laine, P.; Jonas, M.; Wiest, O. J. Org. Chem. 2004, 69, 543.

    Article  CAS  Google Scholar 

  59. Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287.

    Article  CAS  Google Scholar 

  60. Beletskaya, I. P.; Latyshev, G. V.; Tsvetkov, A. V.; Lukashev, N. V. Tetrahedron Lett. 2003, 44, 5011.

    CAS  Google Scholar 

  61. Penney, J. M.; Miller, J. A. Tetrahedron Lett. 2004, 45, 4989.

    CAS  Google Scholar 

  62. McElroy, W. T.; DeShong, P. Org. Lett. 2003, 5, 4779.

    Article  CAS  Google Scholar 

  63. Basu, B.; Freijd, T. Acta Chem. Scand. 1996, 50, 316.

    Article  CAS  Google Scholar 

  64. Niu, C.; Li, J.; Doyle, T. W.; Chen, S.-H. Tetrahedron 1998, 54, 6311.

    Article  CAS  Google Scholar 

  65. Draper, T. L.; Bailey, T. R. Synlett 1995, 157.

    Google Scholar 

  66. Wei, Z-L.; George, C.; Kozikowski, A. P. Terahedron Lett. 2003, 44, 3847.

    CAS  Google Scholar 

  67. Raggon, J. W.; Snyder, W. M. Org. Proc. Res. & Dev. 2002, 6, 67.

    CAS  Google Scholar 

  68. Karig, G.; Moon, M.-T.; Thasana, N.; Gallagher, T. Org. Lett. 2002, 4, 3115.

    Article  CAS  Google Scholar 

  69. Karig, G.; Thasana, N.; Gallagher, Synlett 2002, 808.

    Google Scholar 

  70. Frantz, R.; Granier, M.; Durand, J.-O.; Lanneau, G. F. Tetrahedron Lett. 2002, 43, 9115.

    CAS  Google Scholar 

  71. Zhao, J.; Yang, X.; Jia, X.; Luo, S.; Zhai, H. Tetrahedron 2003, 59, 9379.

    Article  CAS  Google Scholar 

  72. Turner, S. C.; Zhai, H.; Rapoport, H. J. Org. Chem. 2000, 65, 861.

    Article  CAS  Google Scholar 

  73. Sakamoto, T; Arakida, H.; Edo, K.; Yamanka, H. Heterocycles 1981, 16, 965.

    Article  CAS  Google Scholar 

  74. Köhler, K.; Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J. Chem. Eur. J. 2002, 8, 622.

    Google Scholar 

  75. Walker, J. A., II; Chen, J. J.; Hinkley, J. M.; Wise, D. S.; Townsend, L. B. Nucleosides Nucleotides 1997, 16, 1999.

    CAS  Google Scholar 

  76. Ma, S.; Zhang, J.; Lu, L.; Chem. Eur. J., 2003, 9, 2447.

    CAS  Google Scholar 

  77. Aoyagi, Y.; Inoue, A.; Koizumi, I.; Hashimoto, R.; Tokunaga, K.; Gohma, K.; Komatsu, J.; Sekine, K.; Miyafuji, A.; Konoh, J.; Homna, R.; Akita, Y.; Ohta A. Heterocycles 1992, 33, 257.

    CAS  Google Scholar 

  78. Yamashita, M.; Oda, M.; Hayashi, K.; Kawasaki, I.; Ohta, S. Heterocycles, 1998, 48, 2543

    CAS  Google Scholar 

  79. Lee, K.; Seomoon, D.; Lee, P. H. Angew. Chem. Int. Ed. 2002, 41, 3901.

    CAS  Google Scholar 

  80. Takeuchi, R.; Suzuki, K.; Sato, N. Synthesis 1990, 923.

    Google Scholar 

  81. Bessard, Y.; Crettaz, R. Tetrahedron 1999, 55, 405.

    CAS  Google Scholar 

  82. Couve-Bonnaire, S.; Carpentier, J.-F.; Castanet, Y.; Mortreux, A. Tetrahedron Lett. 1999, 40, 3717.

    CAS  Google Scholar 

  83. Bessard, Y.; Roduit, J. P. Tetrahedron 1999, 55, 393.

    CAS  Google Scholar 

  84. Wu, G. G.; Wong, YS; Poirier, M. Org. Lett. 1999, 1, 745.

    CAS  Google Scholar 

  85. Head, R.A.; Ibbotson, A. Tetrahedron Lett. 1984, 25, 5953.

    Article  Google Scholar 

  86. Najiba, D.; Carpentier, J.-F.; Castanet, Y.; Biot, C.; Brocard, J.; Mortreux, A. Tetrahedron Lett. 1999, 40, 3719.

    Article  CAS  Google Scholar 

  87. Ishiyama, T.; Kizaki, H.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1993, 34, 2127.

    Article  Google Scholar 

  88. Couve-Bonnaire, S.; Carpentier, J.-F.; Mortreux, A.; Castanet, Y. Tetrahedron 2003, 59, 2793.

    Article  CAS  Google Scholar 

  89. Hatanaka, Y.; Fukushima, S.; Hiyama, T. Tetrahedron 1992, 48, 2113.

    Article  CAS  Google Scholar 

  90. Wagaw, S.; Buchwald, S.L. J. Org. Chem. 1996, 61, 7240.

    Article  CAS  Google Scholar 

  91. Rupert, K. C.; Henry, J. R.; Dodd, J. H.; Wadsworth, S. A.; Cavender, D. E.; Olini, G. C.; Fahmy, B.; Siekierka, J. J. Bioorg.Med. Chem. Lett. 2003, 13, 347.

    Article  CAS  Google Scholar 

  92. Wolfe, J. P.; Ahman, J.; Sadighi, J. P.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367.

    CAS  Google Scholar 

  93. Jaime-Figueroa, S.; Liu, Y.; Muchowski, J. M.; Putnam, D. G. Tetrahedron Lett. 1998, 39, 1313.

    CAS  Google Scholar 

  94. Huang, X.; Buchwald, S.L. Org. Lett. 2001, 3, 3417.

    CAS  Google Scholar 

  95. Maes, B.U.W.; Loones, K.T.J.; Lemiére, G.L.F.; Dommisse, R.A. Synlett 2003, 1822.

    Google Scholar 

  96. Desmarets, C.; Schneider, R.; Fort, Y. J. Org. Chem. 2002, 67, 3029.

    Article  CAS  Google Scholar 

  97. Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2000, 41, 2881.

    Article  CAS  Google Scholar 

  98. Kiyomori, A.; Marcoux, J. F.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657.

    Article  CAS  Google Scholar 

  99. Arterburn, J.B.; Pannala, M.; Gonzalez, A.M. Tetrahedron Lett. 2001, 42, 1475.

    Article  CAS  Google Scholar 

  100. Li, C.S.; Dixon, D.D. Tetrahedron Lett. 2004, 45, 4257.

    CAS  Google Scholar 

  101. Wolter, M.; Nordmann, G.; Job, G.E.; Buchwald, S.L. Org. Lett. 2002, 4, 973.

    Article  CAS  Google Scholar 

  102. Gelman, D.; Jiang, L.; Buchwald, S.L. Org. Lett. 2003, 5, 2315.

    CAS  Google Scholar 

  103. Berman, A.M.; Johnson, J.S. J. Am. Chem. Soc. 2004, 126, 5680.

    Article  CAS  Google Scholar 

  104. Zanon, J.; Klapars, A.; Buchwald, S.L. J. Am. Cem. Soc. 2003, 125, 2890.

    CAS  Google Scholar 

  105. Klapars, A.; Buchwald, S.L. J. Am. Chem. Soc. 2002, 124, 14844.

    CAS  Google Scholar 

  106. Hennessy, E.J.; Buchwald, S.L. Org. Lett. 2002, 4, 269.

    Article  CAS  Google Scholar 

  107. Akita, Y.; Itagaki, Y.; Takizawa, S.; Ohta, A. Chem. Pharm. Bull. 1989, 37, 1477.

    CAS  Google Scholar 

  108. Wang, L.; Woods, K. W.; Li, Q.; Barr, K. J.; McCroskey, R. W.; Hannick, S. M.; Gherke, L.; Credo, R. B.; Hui, Y.-H.; Marsh, K.; Warner, R.; Lee, J. Y.; Zielinski-Mozng, N.; Frost, D.; Rosenberg, S. H.; Sham, H. L. J. Med. Chem. 2002, 45, 1697.

    CAS  Google Scholar 

  109. Pal, M.; Batchu, V. R.; Parasuraman, K.; Yeleswarapu, K. R. J. Org. Chem. 2003, 68, 6806.

    Article  CAS  Google Scholar 

  110. Inoh, J.-I.; Satoh, T.; Pivsa-Art, S.; Miura, N.; Nomura, M. Tetrahedron Lett. 1998, 39, 4673.

    Article  CAS  Google Scholar 

  111. Vlád, G.; Horváth, I. T. J. Org.Chem. 2002, 67, 6550.

    Google Scholar 

  112. Fort, Y.; Becker, S.; Caubére, P. Tetrahedron 1994, 50, 11893.

    Article  CAS  Google Scholar 

  113. De Franca, K. W. R.; Navarro, M.; Léonel, E.; Durandetti, M.; Nédélec, J.-Y. J. Org. Chem. 2002, 67, 1838.

    Google Scholar 

  114. Itami, K.; Yamazaki, D.; Yoshida, J.-i. Org. Lett. 2003, 5, 2161

    Article  CAS  Google Scholar 

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(2005). The Functionalization of Six Membered Rings. In: Heterocycles from Transition Metal Catalysis. Catalysis by Metal Complexes, vol 28. Springer, Dordrecht. https://doi.org/10.1007/1-4020-3692-2_7

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