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Bibliographical Background: The Ortho Effect in The Catellani Reaction

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Development of New Radical Cascades and Multi-Component Reactions

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Abstract

Pallado-catalyzed sequential reactions involving direct C–H bond activations have emerged as powerful tools for rapid access to complex polycyclic scaffolds, starting from simple precursors. In this context, Professor Marta Catellani has pioneered in the mid 1980s the utilization of norbornene in cooperation with palladium to achieve sequential C-halide and C–H activations via the formation of a five-membered alkylaromatic palladacycle.

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Notes

  1. 1.

    For theoretical explanations on competitive C–C reductive eliminations see: [26–28].

  2. 2.

    Alternatively, radical intermediates have been proposed for this type of processes: [36].

References

  1. Yu, J. Q., Shi, Z. (Eds.). (2010). C-H activation. Topics in current chemistry, 292, 1–379.

    Google Scholar 

  2. Wencel-delord, J., Dröge, T., Liu, F., & Glorius, F. (2011). Chemical Society Reviews, 40, 4740–4761.

    Article  CAS  Google Scholar 

  3. Chiusoli, G. P., Catellani, M., Costa, M., Motti, E., Della Ca, N., & Maestri, G. (2010). Coordination Chemistry Reviews, 254, 456–469.

    Article  CAS  Google Scholar 

  4. Catellani, M., & Chiusoli, G. P. (1985). Journal of Organometallic Chemistry, 286, C13–C16.

    Article  CAS  Google Scholar 

  5. Catellani, M. (2003). Synlett, 298–313.

    Google Scholar 

  6. Catellani, M., Motti, E., & Della Ca, N. (2008). Accounts of Chemical Research, 41, 1512–1522.

    Article  CAS  Google Scholar 

  7. Martins, A., Mariampillai, B., & Lautens, M. (2010). Topics in Current Chemistry, 292, 1–33.

    Article  CAS  Google Scholar 

  8. Amatore, C., & Jutand, A. (2000). Accounts of Chemical Research, 33, 314–321.

    Article  CAS  Google Scholar 

  9. Amatore, C., Jutand, A., Khalil, F. (2006). ARKIVOC, iv, 38–48.

    Google Scholar 

  10. Zawisza, A. M., & Muzart, J. (2007). Tetrahedron Letters, 48, 6738–6742.

    Article  CAS  Google Scholar 

  11. Jeffery, T. (1999). Tetrahedron Letters, 40, 1673–1676.

    Article  CAS  Google Scholar 

  12. Blanchot, M., Candido, D. A., Larnaud, F., & Lautens, M. (2011). Organic Letters, 13, 1486–1489.

    Article  CAS  Google Scholar 

  13. Dieck, H. A., & Heck, R. F. (1974). Journal of the American Chemical Society, 96, 1133–1135.

    Article  CAS  Google Scholar 

  14. Khoury, P. R., Goddard, J. D., & Tam, W. (2004). Tetrahedron, 60, 8103–8112.

    Article  CAS  Google Scholar 

  15. Li, C.-S., Cheng, C.-H., Liao, F.-L., Wang, S. L. (1991). Journal of the Chemical Society, Chemical Communications, 710–712.

    Google Scholar 

  16. Catellani, M., Mealli, C., Motti, E., Paoli, P., Perez-Carreno, E., & Pregosin, P. S. (2002). Journal of the American Chemical Society, 124, 4336–4346.

    Article  CAS  Google Scholar 

  17. Catellani, M., & Chiusoli, G. P. (1992). Journal of Organometallic Chemistry, 425, 151–154.

    Article  CAS  Google Scholar 

  18. Martin-Matute, B., Mateo, C., Cardenas, D. J., & Echavarren, A. M. (2001). Chemistry--A European Journal, 7, 2341–2348.

    Article  CAS  Google Scholar 

  19. Garcia-Cuadrado, D., Braga, A. A. C., Maseras, F., & Echavarren, A. M. (2006). Journal of the American Chemical Society, 128, 1066–1067.

    Article  CAS  Google Scholar 

  20. Garcia-Cuadrado, D., Mendoza, P., Braga, A. A. C., Maseras, F., & Echavarren, A. M. (2007). Journal of the American Chemical Society, 129, 6880–6886.

    Article  CAS  Google Scholar 

  21. Chiusoli, G. P., & Catellani, M. (1992). Journal of Organometallic Chemistry, 437, 369–373.

    Article  Google Scholar 

  22. Liu, C.-H., Li, C.-S., & Cheng, C.-H. (1994). Organomettallics, 13, 18–20.

    Article  CAS  Google Scholar 

  23. Byers, P. K., Canty, A. J., Skelton, B. W., White, A. H. (1986). Journal of the Chemical Society, Chemical Communications, 1722–1724.

    Google Scholar 

  24. Bocelli, G., Catellani, M., & Ghelli, S. (1993). Journal of Organometallic Chemistry, 458, C12–C15.

    Article  CAS  Google Scholar 

  25. Rudolph, A., Rackelmann, N., & Lautens, M. (2007). Angewandte Chemie International Edition, 46, 1485–1488.

    Article  CAS  Google Scholar 

  26. Ananikov, V. P., Musaev, D. G., & Morokuma, K. (2005). Organometallics, 24, 715–723.

    Article  CAS  Google Scholar 

  27. Ananikov, V. P., Musaev, D. G., & Morokuma, K. (2007). European Journal of Inorganic Chemistry, 34, 5390–5399.

    Article  Google Scholar 

  28. Ananikov, V. P., Musaev, D. G., Morokuma, K. (2002). Journal of the American Chemical Society, 124, 2839–2852 and references cited therein.

    Google Scholar 

  29. Terpko, M. O., & Heck, R. F. (1979). Journal of the American Chemical Society, 101, 5281–5283.

    Article  CAS  Google Scholar 

  30. Catellani, M. (2003). Synlett, 298–313.

    Google Scholar 

  31. Wilhem, T., & Lautens, M. (2005). Organic Letters, 7, 4053–4056.

    Article  Google Scholar 

  32. Catellani, M., Frignani, F., & Rangoni, M. (1997). Angewandte Chemie International Edition, 36, 119–122.

    Article  CAS  Google Scholar 

  33. Catellani, M., Motti, E., Minari, M. (2000). Journal of the Chemical Society, Chemical Communications, 157–158.

    Google Scholar 

  34. Motti, E., Rosseti, M., Bocelli, G., & Catellani, M. (2004). Journal of Organometallic Chemistry, 689, 3741–3749.

    Article  CAS  Google Scholar 

  35. Alberico, D., Rudolph, A., & Lautens, M. (2007). Journal of Organic Chemistry, 72, 775–781.

    Article  CAS  Google Scholar 

  36. Lyons, T. W., & Sanford, M. S. (2010). Chemical Reviews, 110, 1147–1169.

    Article  CAS  Google Scholar 

  37. Canty, A. J., Patel, J., Rodeman, T., Ryan, J. H., Skelton, B. W., & White, A. H. (2004). Organometallics, 23, 3466–3473.

    Article  CAS  Google Scholar 

  38. Dick, A., Kampf, J. W., & Sanford, M. S. (2005). Journal of the American Chemical Society, 127, 12790–12791.

    Article  CAS  Google Scholar 

  39. Albrecht, K., Reiser, O., Weber, M., Knieriem, B., & de Meijere, A. (1994). Tetrahedron, 50, 383–401.

    Article  CAS  Google Scholar 

  40. Catellani, M., Motti, E. (1998). New Journal of Chemistry, 759–761.

    Google Scholar 

  41. Catellani, M., Motti, E., & Baratta, S. (2001). Organic Letters, 3, 3611–3614.

    Article  CAS  Google Scholar 

  42. Dyker, G., Korning, P. J., Jones, P. G., & Bubenitschek, P. (1993). Angewandte Chemie International Edition, 32, 1733–1735.

    Article  Google Scholar 

  43. Mauleón, P., Núñez, A. A., Alonso, I., & Carretero, J. C. (2003). Chemistry--A European Journal, 9, 1511–1520.

    Article  Google Scholar 

  44. Alonso, I., Alcami, M., Mauleon, P., & Carretero, J. C. (2006). Chemistry--A European Journal, 12, 4576–4583.

    Article  CAS  Google Scholar 

  45. Motti, E., Ippomei, G., Deledda, S., Catellani, M. (2003). Synthesis, 2671–2678.

    Google Scholar 

  46. Catellani, M., Deledda, S., Ganchegi, B., Henin, F., Motti, E., & Muzart, J. (2003). Journal of Organometallic Chemistry, 687, 473–482.

    Article  CAS  Google Scholar 

  47. Faccini, F., Motti, E., & Catellani, M. (2004). Journal of the American Chemical Society, 126, 78–79.

    Article  CAS  Google Scholar 

  48. Motti, E., Catellani, M. (2003). Journal of Molecular Catalysis A: Chemical, 204–205, 115–124.

    Google Scholar 

  49. Catellani, M., Motti, E., & Della Ca, N. (2008). Accounts of Chemical Research, 41, 1512–1522.

    Article  CAS  Google Scholar 

  50. Mariampillai, B., Alliot, J., Li, M., & Lautens, M. (2007). Journal of the American Chemical Society, 129, 15372–15379.

    Article  CAS  Google Scholar 

  51. Zhao, Y.-B., Mariampillai, B., Candito, D. A., Laleu, B., Li, M., & Lautens, M. (2009). Angewandte Chemie International Edition, 48, 1849–1852.

    Article  CAS  Google Scholar 

  52. Quan, L. G., Gevorgyan, V., & Yamamoto, Y. (1999). Journal of the American Chemical Society, 121, 3545–3546.

    Article  CAS  Google Scholar 

  53. Catellani, M., Motti, E., & Baratta, S. (2001). Organic Letters, 3, 3611–3614.

    Article  CAS  Google Scholar 

  54. Della Ca, N., Maestri, G., & Catellani, M. (2009). Chemistry--A European Journal, 15, 7850–7853.

    Article  CAS  Google Scholar 

  55. Maestri, G., Della Ca, N., Catellani, M. (2009). Chem. Commun, 4892–4894.

    Google Scholar 

  56. Motti, E., Faccini, F., Ferrari, I., Catellani, M., & Ferracioli, R. (2006). Organic Letters, 8, 3967–3970.

    Article  CAS  Google Scholar 

  57. Ferraccioli, R., Carenzi, D., Rombola, O., & Catellani, M. (2004). Organic Letters, 6, 4759–4762.

    Article  CAS  Google Scholar 

  58. Catellani, M., Motti, E., & Della Ca, N. (2010). Topics in Catalysis, 53, 991–996.

    Article  CAS  Google Scholar 

  59. Mann, G., Hartwig, J. F., Driver, M. S., & Fernandez-Rivas, C. (1998). Journal of the American Chemical Society, 120, 827–828.

    Article  CAS  Google Scholar 

  60. Barluenga, J., Aznar, F., & Valdes, C. (2004). Angewandte Chemie International Edition, 43, 343–345.

    Article  CAS  Google Scholar 

  61. Candito, D. A., & Lautens, M. (2009). Angewandte Chemie International Edition, 48, 6713–6716.

    Article  CAS  Google Scholar 

  62. Dyker, G. (1994). Chemische Berichte, 127, 739–742.

    Article  CAS  Google Scholar 

  63. Ozawa, F., Fujimori, M., Yamamoto, T., & Yamamoto, A. (1986). Organometallics, 5, 2144–2149.

    Article  CAS  Google Scholar 

  64. Suzaki, Y., & Osakada, K. (2003). Organometallics, 22, 2193–2197.

    Article  CAS  Google Scholar 

  65. Cardenas, D. J., Martin-Matute, B., & Echavarren, A. (2006). Journal of the American Chemical Society, 128, 5033–5040.

    Article  CAS  Google Scholar 

  66. Maestri, G., Motti, E., Della Ca, N., Malacria, M., Derat, E., & Catellani, M. (2011). Journal of the American Chemical Society, 133, 8574–8585.

    Article  CAS  Google Scholar 

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  1. Stockwell laboratory, Department of Biological Sciences, Columbia University, 550 West 120th Street, New York, NY, 10027, USA

    Marie-Hélène Larraufie

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Larraufie, MH. (2014). Bibliographical Background: The Ortho Effect in The Catellani Reaction. In: Development of New Radical Cascades and Multi-Component Reactions. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-01324-4_7

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