Advertisement

General Introduction

Chapter
  • 842 Downloads
Part of the Springer Theses book series (Springer Theses)

Abstract

As the title above suggests, this first chapter is devoted to make a general introduction to the main topic of this present thesis: the Pd-catalyzed cross-coupling reactions. With this aim, in the first part of this chapter the concept of catalysis, its origin, as well as other related topics will be briefly introduced. Next, in the second part of this chapter, the definition of C–C cross-coupling reactions and a summary of their generally accepted reaction pathway will be presented. Finally, the elementary steps that take part in this type of reactions will be described separately. Furthermore, for each of these steps, the most relevant mechanistic studies on Pd-catalyzed C–C cross-coupling reactions reported in the last years, with particular attention to the theoretical ones, will be reviewed. In principle, all the concepts provided in this first chapter should be more than enough to contextualize all the results obtained in the course of this thesis, and that are presented in Chaps. 4, 5 and 6.

Keywords

Maleic Anhydride Catalytic Cycle Maleic Anhydride Oxidative Addition Phosphine Ligand 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    Berzelius, J.J.: Annales chimie physiques 61, 146 (1836)Google Scholar
  2. 2.
    Leicester, H.M., Klickstein, H.S.: Source Book in Chemistry 1400–1900. Harvard University Press, Massachusetts (1965)Google Scholar
  3. 3.
    Arrhenius, S.: Zeit. Phys. Chem. 28, 317 (1899)Google Scholar
  4. 4.
    Rothenberg, G.: Catalysis: Concepts and Green Applications. Wiley-VCH, Weinheim (2008)Google Scholar
  5. 5.
    Eyring, H.: J. Chem. Phys. 3, 107 (1935)CrossRefGoogle Scholar
  6. 6.
    Evans, M.G., Polanyi, M.: Trans. Faraday Soc. 31, 875 (1935)CrossRefGoogle Scholar
  7. 7.
    Hartwig, J.: Organotransition Metal Chemistry: From Bonding to Catalysis. University Science Books, California (2010)Google Scholar
  8. 8.
    Kozuch, S., Shaik, S.: J. Am. Chem. Soc. 128, 3355 (2006)CrossRefGoogle Scholar
  9. 9.
    Kozuch, S., Shaik, S.: J. Phys. Chem. A 112, 6032 (2008)CrossRefGoogle Scholar
  10. 10.
    Uhe, A., Kozuch, S., Shaik, S.: J. Comput. Chem. 32, 978 (2011)CrossRefGoogle Scholar
  11. 11.
    Kozuch, S., Shaik, S.: Acc. Chem. Res. 44, 101 (2011)CrossRefGoogle Scholar
  12. 12.
    Beller, M., Bolm, C. (eds.): Transition Metals for Organic Synthesis, 2nd edn. Wiley-VCH, Weinheim (2004)Google Scholar
  13. 13.
    de Meijere, A., Diedrich, F. (eds.): Metal-Catalyzed Cross-Coupling Reactions, 2nd edn. Wiley-VCH, Weinheim (2004)Google Scholar
  14. 14.
    Miyaura, N. (ed.): Cross-Coupling Reactions: A Practical Guide, No. 219 in Topics in Current Chemistry. Springer, Berlin (2002)Google Scholar
  15. 15.
    Buchwald, S.L. (ed.): Acc. Chem. Res. 41(special issue), 1439 (2008)Google Scholar
  16. 16.
    Tamao, K., Hiyama, T., Negishi, E.-I. : J. Organomet. Chem. 653(special issue), 1 (2002)Google Scholar
  17. 17.
    Phapale, V.B., Cárdenas, D.J.: Chem. Soc. Rev. 38, 1598 (2009)Google Scholar
  18. 18.
    Nicolaou, K.C., Bulger, P.G., Sarlah, D.: Angew. Chem. Int. Ed. 44, 4442 (2005)CrossRefGoogle Scholar
  19. 19.
    Negishi, E.-I., Hu, Q., Huang, Z., Wang, G., Yin, N.: The Chemistry of Organozinc Compounds, pp. 457–553. In: Rappoport, Z.Z., Marek, I. (eds.). Wiley , England (2006)Google Scholar
  20. 20.
    Kosugi, M., Sasazawa, K., Shimizu, Y., Migita, T.: Chem. Lett. 3, 301 (1977)CrossRefGoogle Scholar
  21. 21.
    Stille, J.K.: Angew. Chem. Int. Ed. 25, 508 (1986)CrossRefGoogle Scholar
  22. 22.
    Espinet, P., Echavarren, A.M.: Angew. Chem. Int. Ed. 43, 4704 (2004)Google Scholar
  23. 23.
    Miyaura, N., Yamada, K., Suzuki, A.: Tetrahedron Lett. 20, 3437 (1979)CrossRefGoogle Scholar
  24. 24.
    Miyaura, N., Suzuki, A.: Chem. Rev. 95, 2457 (1995)CrossRefGoogle Scholar
  25. 25.
    Negishi, E.-I., King, A.O., Okukado, N.: J. Org. Chem. 1977, 42 (1821)Google Scholar
  26. 26.
    Nicolaou, K. C., Sorensen, E.J.: Classics in Total Synthesis, Chap. 31. VCH, New York (1996)Google Scholar
  27. 27.
    Chemler, S.R., Trauner, D., Danishefsky, S.J., Angew, : Angew. Chem. Int. Ed. 40, 4544 (2001)CrossRefGoogle Scholar
  28. 28.
    Negishi, E.-I.: Bull. Chem. Soc. Jpn. 80, 233 (2007)CrossRefGoogle Scholar
  29. 29.
    Anderson, B., Becke, L., Booher, R., Flaugh, M., Harn, N., Kress, T., Varie, D., Wepsiec, J.: J. Org. Chem. 62, 8634 (1997)CrossRefGoogle Scholar
  30. 30.
    Rouhi, A.M.: Chem. Eng. News 82, 49 (2004)Google Scholar
  31. 31.
    Zapf, A., Beller, M.: Top. Catal. 19, 101 (2002)CrossRefGoogle Scholar
  32. 32.
    Corbet, J.P., Mignani, G.: Chem. Rev. 106, 2651 (2006)CrossRefGoogle Scholar
  33. 33.
    Zapf, A., Beller, M.: Handbook of Organopalladium Chemistry for Organic Synthesis. In: Negishi, E.-I. (ed.). Wiley, New York (2002)Google Scholar
  34. 34.
    Blaser, H.U., Indolese, A., Naud, F., Nettekoven, U., Schnyder, A.: Adv. Synth. Catal. 346, 1583 (2004)CrossRefGoogle Scholar
  35. 35.
    Tamura, M., Kochi, J.: J. Am. Chem. Soc. 93, 1483 (1971)CrossRefGoogle Scholar
  36. 36.
    Tamura, M., Kochi, J.: J. Am. Chem. Soc. 93, 1485 (1971)CrossRefGoogle Scholar
  37. 37.
    Tamura, M., Kochi, J.K.: J. Organomet. Chem. 42, 205 (1972)CrossRefGoogle Scholar
  38. 38.
    Ishiyama, T., Abe, S., Miyaura, N., Suzuki, A.: Chem. Lett. 691 (1992)Google Scholar
  39. 39.
    Devasagayaraj, A., Studemann, T., Knochel, P.: Angew. Chem. Int. Ed. 34, 2723 (1996)CrossRefGoogle Scholar
  40. 40.
    Giovannini, R., Studemann, T., Dussin, G., Knochel, P.: Angew. Chem. Int. Ed. 37, 2387 (1998)CrossRefGoogle Scholar
  41. 41.
    Giovannini, R., Studemann, T., Devasagayaraj, A., Dussin, G., Knochel, P.: J. Org. Chem. 64, 3544 (1999)CrossRefGoogle Scholar
  42. 42.
    Jensen, A.E., Knochel, P.: J. Org. Chem. 67, 79 (2002)CrossRefGoogle Scholar
  43. 43.
    Frisch, A.C., Beller, M.: Angew. Chem. Int. Ed. 44, 674 (2005)CrossRefGoogle Scholar
  44. 44.
    Littke, A.F., Fu, G.C.: Angew. Chem. Int. Ed. 41, 4176 (2002)CrossRefGoogle Scholar
  45. 45.
    Wolfe, J.P., Singer, R.A., Yang, B.H., Buchwald, S.L.: J. Am. Chem. Soc. 121, 9550 (1999)CrossRefGoogle Scholar
  46. 46.
    Zapf, A., Ehrentraut, A., Beller, M.: Angew. Chem. Int. Ed. 39, 4153 (2000)CrossRefGoogle Scholar
  47. 47.
    Fleckenstein, C.A., Plenio, H.: Chem. Soc. Rev. 39, 694 (2010)CrossRefGoogle Scholar
  48. 48.
    Kantchev, E.A.B., O’Brien, C.J., Organ, M.G.: Angew. Chem. Int. Ed. 46, 2768 (2007)CrossRefGoogle Scholar
  49. 49.
    Marion, N., Nolan, S.P.: Acc. Chem. Res. 41, 1440 (2008)CrossRefGoogle Scholar
  50. 50.
    García-Cuadrado, D., Mendoza, de P., Braga, A.A.C., Maseras, F., Echavarren, A.M.: J. Am. Chem. Soc. 129, 6880 (2007)Google Scholar
  51. 51.
    Alberico, D., Scott, M.E., Lautens, M.: Chem. Rev. 107, 174 (2007)CrossRefGoogle Scholar
  52. 52.
    Özdemir, I., Demir, S., Çetinkaya, B., Gourlaouen, C., Maseras, F., Bruneau, C., Dixneuf, P.H.: J. Am. Chem. Soc. 130, 1156 (2008)Google Scholar
  53. 53.
    Ackermann, L., Vicente, R., Kapdi, A.R.: Angew. Chem. Int. Ed. 48, 9792 (2009)CrossRefGoogle Scholar
  54. 54.
    Chiusoli, G.P., Catellani, M., Costa, M., Motti, E., Della Ca’, N., Maestri, G.: Coord. Chem. Rev. 254, 456 (2010)Google Scholar
  55. 55.
    Amatore, C., Jutand, A.: Acc. Chem. Res. 33, 314 (2000)CrossRefGoogle Scholar
  56. 56.
    Galardon, E., Ramdeehul, S., Brown, J.M., Cowley, A., Hii, K.K.M., Jutand, A.: Angew. Chem. Int. Ed. 41, 1760 (2002)CrossRefGoogle Scholar
  57. 57.
    Hartwig, J.F.: Inorg. Chem. 2007, 46 (1936)Google Scholar
  58. 58.
    Yandulov, D.V., Tran, N.T.: J. Am. Chem. Soc. 129, 1342 (2007)CrossRefGoogle Scholar
  59. 59.
    Senn, H.M., Ziegler, T.: Organometallics 23, 2980 (2004)CrossRefGoogle Scholar
  60. 60.
    Goossen, L.J., Koley, D., Hermann, H.L., Thiel, W.: Organometallics 24, 2398 (2005)CrossRefGoogle Scholar
  61. 61.
    Pérez-Rodríguez, M., Braga, A.A.C., García-Melchor, M., Pérez-Temprano, M.H., Casares, J.A., Ujaque, G., de Lera, A.R., Álvarez, R., Maseras, F., Espinet, P.: J. Am. Chem. Soc. 131, 3650 ( 2009)Google Scholar
  62. 62.
    Xue, L., Lin, Z.: Chem. Soc. Rev. 39, 1692 (2010)CrossRefGoogle Scholar
  63. 63.
    Casado, A.L., Espinet, P.: J. Am. Chem. Soc. 120, 8978 (1998)CrossRefGoogle Scholar
  64. 64.
    Goossen, L.J., Koley, D., Hermann, H.L., Thiel, W.: J. Am. Chem. Soc. 127, 11102 (2005)CrossRefGoogle Scholar
  65. 65.
    Sicre, C., Braga, A.A.C., Maseras, F., Cid, M.M.: Tetrahedron 64, 7437 (2008)CrossRefGoogle Scholar
  66. 66.
    Liu, Q., Lan, Y., Liu, J., Li, G., Wu, Y.-D., Lei, A.: J. Am. Chem. Soc. 131, 10201 (2009)Google Scholar
  67. 67.
    Casares, J.A., Espinet, P., Fuentes, B., Salas, G.: J. Am. Chem. Soc. 129, 3508 (2007)CrossRefGoogle Scholar
  68. 68.
    Álvarez, R., Faza, O.N., López, C.S., de Lera, A.R. Org. Lett. 8, 35 (2006)Google Scholar
  69. 69.
    Amatore, C., Jutand, A., Le Duc, G.: Chem. Eur. J. 17, 2492 (2011)CrossRefGoogle Scholar
  70. 70.
    Braga, A.A.C., Morgon, N.H., Ujaque, G., Maseras, F.: J. Am. Chem. Soc. 127, 9298 (2005)CrossRefGoogle Scholar
  71. 71.
    Braga, A.A.C., Ujaque, G., Maseras, F.: Organometallics 25, 3647 (2006)CrossRefGoogle Scholar
  72. 72.
    Braga, A.A.C., Morgon, N.H., Ujaque, G., Lledós, A., Maseras, F.: J. Organomet. Chem. 691, 4459 (2006)Google Scholar
  73. 73.
    Nova, A., Ujaque, G., Maseras, F., Lledós, A., Espinet, P.: J. Am. Chem. Soc. 128, 14571 (2006)Google Scholar
  74. 74.
    Pérez-Temprano, M. H., Nova, A., Casares, J.A., Espinet, P.: J. Am. Chem. Soc. 130, 10518 (2008)Google Scholar
  75. 75.
    Fuentes, B., García-Melchor, M., Lledós, A., Maseras, F., Casares, J.A., Ujaque, G., Espinet, P.: Chem. Eur. J. 16, 8596 (2010)Google Scholar
  76. 76.
    García-Melchor, M., Fuentes, B., Lledós, A., Casares, J.A., Ujaque, G., Espinet, P.: J. Am. Chem. Soc. 133, 13519 (2011)Google Scholar
  77. 77.
    García-Melchor, M., Pacheco, M.C., Nájera, C., Lledós, A., Ujaque, G.: ACS Catal. 2, 135 (2012)Google Scholar
  78. 78.
    Noell, J.O., Hay, P.J.: J. Am. Chem. Soc. 104, 4578 (1982)CrossRefGoogle Scholar
  79. 79.
    Low, J.J., Goddard, W.A.: J. Am. Chem. Soc. 106, 6928 (1984)CrossRefGoogle Scholar
  80. 80.
    Obara, S., Kitaura, K., Morokuma, K.: J. Am. Chem. Soc. 106, 7482 (1984)CrossRefGoogle Scholar
  81. 81.
    Bickelhaupt, F.M., Ziegler, T., Schleyer, P.V.R.: Organometallics 14, 2288 (1995)CrossRefGoogle Scholar
  82. 82.
    Ahlquist, M., Norrby, P.O.: Organometallics 26, 550 (2007)CrossRefGoogle Scholar
  83. 83.
    Li, Z., Fu, Y., Guo, Q.-X., Liu, L.: Organometallics 27, 4043 (2008)CrossRefGoogle Scholar
  84. 84.
    Jover, J., Fey, N., Purdie, M., Lloyd-Jones, G.C., Harvey, J.N.: J. Mol. Catal. A 324, 39 (2010)CrossRefGoogle Scholar
  85. 85.
    Schoenebeck, F., Houk, K.N.: J. Am. Chem. Soc. 132, 2496 (2010)CrossRefGoogle Scholar
  86. 86.
    Stille, J.K., Lau, K.S.Y.: Acc. Chem. Res. 10, 434 (1997)CrossRefGoogle Scholar
  87. 87.
    Casado, A.L., Casares, J.A., Espinet, P.: Inorg. Chem. 37, 4154 (1998)CrossRefGoogle Scholar
  88. 88.
    Netherton, M.R., Fu, G.C.: Angew. Chem. Int. Ed. 41, 3910 (2002)CrossRefGoogle Scholar
  89. 89.
    Hills, I.D., Netherton, M.R., Fu, G.C.: Angew. Chem. Int. Ed. 42, 5749 (2003)CrossRefGoogle Scholar
  90. 90.
    Gourlaouen, C., Ujaque, G., Lledós, A., Medio-Simón, M., Asensio, G., Maseras, F.: J. Org. Chem. 74, 4049 (2009)Google Scholar
  91. 91.
    Crabtree, R.H.: The Organometallic Chemistry of the Transition Metals, 3rd edn. John Wiley-Interscience, New York (2001)Google Scholar
  92. 92.
    Lappert, M., Lednor, P.: Adv. Organomet. Chem. 14, 345 (1976)CrossRefGoogle Scholar
  93. 93.
    Kurosawa, H., Ogoshi, S., Kawasaki, Y., Murai, S., Miyoshi, M., Ikeda, I.: J. Am. Chem. Soc. 112, 2813 (1990)CrossRefGoogle Scholar
  94. 94.
    Kurosawa, H., Kajimaru, H., Ogoshi, S., Yoneda, H., Miki, K., Kasai, N., Murai, S., Ikeda, I.: J. Am. Chem. Soc. 114, 8417 (1992)CrossRefGoogle Scholar
  95. 95.
    Astruc, D.: Organometallic Chemistry and Catalysis. Springer, Berlin (2007)Google Scholar
  96. 96.
    Amatore, C., Jutand, A.: J. Organomet. Chem. 576, 254 (1999)CrossRefGoogle Scholar
  97. 97.
    Kozuch, S., Amatore, C., Jutand, A., Shaik, S.: Organometallics 24, 2319 (2005)CrossRefGoogle Scholar
  98. 98.
    Diefenbach, A., de Jong, G.T., Bickelhaupt, F.M.: J. Chem. Theory Comput. 1, 286 (2005)CrossRefGoogle Scholar
  99. 99.
    Ariafard, A., Lin, Z.: Organometallics 25, 4030 (2006)CrossRefGoogle Scholar
  100. 100.
    Hartwig, J.F., Paul, F.: J. Am. Chem. Soc. 117, 5373 (1995)CrossRefGoogle Scholar
  101. 101.
    Ahlquist, M., Fristrup, P., Tanner, D., Norrby, P.O.: Organometallics 25, 2066 (2006)CrossRefGoogle Scholar
  102. 102.
    Lam, K.C., Marder, T.B., Lin, Z.Y.: Organometallics 26, 758 (2007)CrossRefGoogle Scholar
  103. 103.
    Barrios-Landeros, F., Carrow, B.P., Hartwig, J.F.: J. Am. Chem. Soc. 131, 8141 (2009)CrossRefGoogle Scholar
  104. 104.
    McMullin, C.L., Jover, J., Harvey, J.N., Fey, N.: Dalton Trans. 39, 10833 (2010)CrossRefGoogle Scholar
  105. 105.
    Besora, M., Gourlaouen, C., Yates, B., Maseras, F.: Dalton Trans. 40, 11089 (2011)CrossRefGoogle Scholar
  106. 106.
    García-Melchor, M., Ujaque, G., Maseras, F., Lledós, A., in Phosphorus Compounds: Advanced Tools in Catalysis and Material Sciences, vol. 37., Chap. 3, pp. 57–84 . In: Peruzzini, M., Gonsalvi, L. (eds.). Springer, Berlin (2011)Google Scholar
  107. 107.
    Farina, V.: Comprehensive Organometallic Chemistry II, vol. 12, Chap. 3.4. In: Abel, E.W., Stone, F., Wilkinson, G., Hegedus, L.S. Elsevier, Oxford (1995)Google Scholar
  108. 108.
    Osakada, K.: Fundamentals of Molecular Catalysis, Current Methods in Inorganic Chemistry, Chap. 5. In: Kurosawa, H., Yamamoto, A. (eds.). Elsevier, Amsterdam (2003)Google Scholar
  109. 109.
    Marshall, J.A.: Chem. Rev. 100, 3163 (2000)CrossRefGoogle Scholar
  110. 110.
    Pérez-Temprano, M.H., Gallego, A.M., Casares, J.A., Espinet, P. Organometallics, 30, 611 (2011)Google Scholar
  111. 111.
    Tatsumi, K., Hoffmann, R., Yamamoto, A., Stille, J.K.: Bull. Chem. Soc. Jpn. 1981, 54 (1857)Google Scholar
  112. 112.
    Low, J.J., Goddard, W.A.: J. Am. Chem. Soc. 108, 6115 (1986)CrossRefGoogle Scholar
  113. 113.
    Low, J.J., Goddard, W.A.: Organometallics 5, 609 (1986)CrossRefGoogle Scholar
  114. 114.
    Ananikov, V.P., Musaev, D.G., Morokuma, K.: J. Am. Chem. Soc. 124, 2839 (2002)CrossRefGoogle Scholar
  115. 115.
    Ananikov, V.P., Musaev, D.G., Morokuma, K.: Organometallics 24, 715 (2005)CrossRefGoogle Scholar
  116. 116.
    Ananikov, V.P., Musaev, D.G., Morokuma, K.: Eur. J. Inorg. Chem. 5390 (2007)Google Scholar
  117. 117.
    Zuidema, E., van Leeuwen, P.W.N.M., Bo, C.: Organometallics 24, 3703 (2005)CrossRefGoogle Scholar
  118. 118.
    Ariafard, A., Yates, B.F.: J. Organomet. Chem. 694, 2075 (2009)CrossRefGoogle Scholar
  119. 119.
    Ziegler, T., Rauk, A.: Theor. Chim. Acta. 46, 1 (1977)Google Scholar
  120. 120.
    Bickelhaupt, F.M.: J. Comput. Chem. 20, 114 (1999)CrossRefGoogle Scholar
  121. 121.
    Negishi, E.-I., Takahashi, T., Akiyoshi, K.: J. Organomet. Chem. 334, 181 (1987)CrossRefGoogle Scholar
  122. 122.
    Pérez-Rodríguez, M., Braga, A.A.C., de Lera, A.R., Maseras, F., Álvarez, R., Espinet, P. Organometallics, 29, 4983 (2010)Google Scholar
  123. 123.
    Méndez, M., Cuerva, J.M., Gómez-Bengoa, E., Cárdenas, D.J., Echavarren, A.M.: Chem. Eur. J. 8, 3620 (2002)Google Scholar

Copyright information

© Springer International Publishing Switzerland 2013

Authors and Affiliations

  1. 1.Department of ChemistryAutonomous University of BarcelonaCerdanyola del VallèsSpain

Personalised recommendations