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Chelate-Directed Oxidative Functionalization of Carbon–Hydrogen Bonds: Synthetic Applications and Mechanistic Insights

  • Dipannita Kalyani
  • Melanie S. SanfordEmail author
Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 24)

Abstract

This chapter describes advances over the past four decades in Pd-mediated and Pd-catalyzed reactions for the highly regioselective oxidative functionalization of C–H bonds. The synthetic utility and the key mechanistic features of both stoichiometric and catalytic C–X (X = O, Cl, Br, I, F, N) bond-forming reactions are presented. The intermediacy of high oxidation state PdIV species in many of these transformations has allowed for bond constructions that were not previously possible through traditional Pd0/PdII couples.

C–H bond cleavage Chelation Carbon–heteroatom Palladium Palladium(IV)  

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References

  1. 1.
    Cope AC, Siekman RW (1965) J Am Chem Soc 87:3272 CrossRefGoogle Scholar
  2. 2.
    Ryabov AD (1985) Synthesis 233 Google Scholar
  3. 3.
    Newkome GR, Puckett WE, Gupta VK, Kiefer GE (1986) Chem Rev 86:451 CrossRefGoogle Scholar
  4. 4.
    Dunina VV, Zalevskaya OA, Potapov VM (1988) Russ Chem Rev 57:434 CrossRefGoogle Scholar
  5. 5.
    Constable AG, McDonald WS, Sawkins LC, Shaw BL (1978) J Chem Soc Chem Commun 1061 Google Scholar
  6. 6.
    Constable AG, McDonald WS, Sawkins LC, Shaw BL (1980) J Chem Soc Dalton Trans 1992 Google Scholar
  7. 7.
    Baldwin JE, Jones RH, Najera C, Yus M (1985) Tetrahedron 41:699 CrossRefGoogle Scholar
  8. 8.
    Baldwin JE, Nájera C, Yus M (1985) J Chem Soc Chem Commun 126 Google Scholar
  9. 9.
    Mahapatra AK, Bandyopadhyay D, Bandyopadhyay P, Chakravorty A (1986) Inorg Chem 25:2214 CrossRefGoogle Scholar
  10. 10.
    Sinha C, Bandyopadhyay D, Chakravorty A (1988) Inorg Chem 27:1173 CrossRefGoogle Scholar
  11. 11.
    Pal CK, Chattopadhyay S, Sinha C, Chakravorty A (1992) J Organomet Chem 439:91 CrossRefGoogle Scholar
  12. 12.
    Sinha CR, Bandyopadhyay D, Chakravorty A (1988) J Chem Soc Chem Commun 468 Google Scholar
  13. 13.
    Bhaumik R, Bandyopadhyay P (1996) Transition Met Chem 21:187 CrossRefGoogle Scholar
  14. 14.
    Alsters PL, Teunissen HT, Boersma J, van Koten G (1990) Recl Trav Chim Pays Bas 109:487 Google Scholar
  15. 15.
    Alsters PL, Teunissen HT, Boersma J, Spek AL, van Koten G (1993) Organometallics 12:4691 CrossRefGoogle Scholar
  16. 16.
    Valk J, Boersma J, van Koten G (1996) Organometallics 15:4366 CrossRefGoogle Scholar
  17. 17.
    Mahapatra AK, Bandyopadhyay D, Bandyopadhyay P, Chakravorty A (1984) J Chem Soc Chem Commun 999 Google Scholar
  18. 18.
    Kamaraj K, Bandyapadhyay D (1997) J Am Chem Soc 119:8099 CrossRefGoogle Scholar
  19. 19.
    Kamaraj K, Bandyapadhyay D (1999) Organometallics 18:438 CrossRefGoogle Scholar
  20. 20.
    Wadhwani P, Bandyapadhyay D (2000) Organometallics 19:4435 CrossRefGoogle Scholar
  21. 21.
    Bhaumik R, Biswas H, Bandyopadhyay P (1995) J Organomet Chem 498:81 CrossRefGoogle Scholar
  22. 22.
    Alsters PL, Boersma J, van Koten G (1991) Tetrahedron Lett 32:675 CrossRefGoogle Scholar
  23. 23.
    Alsters PL, Boersma J, van Koten G (1993) Organometallics 12:1629 CrossRefGoogle Scholar
  24. 24.
    Bäckvall J (1975) Tetrahedron Lett 16:2225 CrossRefGoogle Scholar
  25. 25.
    Bäckvall J, Björkman EE (1980) J Org Chem 45:2893 CrossRefGoogle Scholar
  26. 26.
    Carr K, Sutherland JK (1984) J Chem Soc Chem Commun 1227 Google Scholar
  27. 27.
    Carr K, Saxton HM, Sutherland JK (1988) J Chem Soc Perkin Trans 1599 Google Scholar
  28. 28.
    Bore L, Honda T, Gribble GW (2000) J Org Chem 65:6278 CrossRefGoogle Scholar
  29. 29.
    Justicia J, Oltra JE, Cuerva JM (2004) Tetrahedron Lett 45:4293 CrossRefGoogle Scholar
  30. 30.
    Justicia J, Oltra JE, Cuerva JM (2005) J Org Chem 70:8265 CrossRefGoogle Scholar
  31. 31.
    Dick AR, Kampf JW, Sanford MS (2005) J Am Chem Soc 127:12790 CrossRefGoogle Scholar
  32. 32.
    Alsters PL, Engel PF, Hogerheide MP, Copijn M, Spek AL, van Koten G (1993) Organometallics 12:1831 CrossRefGoogle Scholar
  33. 33.
    Lagunas M, Gossage RA, Spek AL, van Koten G (1998) Organometallics 17:731 CrossRefGoogle Scholar
  34. 34.
    Vicente J, Saura-Llamas I, Bautista D (2005) Organometallics 24:6001 CrossRefGoogle Scholar
  35. 35.
    Bartolomé C, Espinet P, Martín-Álvarez JM, Villafañe F (2003) Inorg Chim Acta 347:49 CrossRefGoogle Scholar
  36. 36.
    Dick AR, Remy MS, Kampf JW, Sanford MS (2007) Organometallics 26:1365 CrossRefGoogle Scholar
  37. 37.
    Yu J, Giri R, Chen X (2006) Org Biomol Chem 4:4041 CrossRefGoogle Scholar
  38. 38.
    Dick AR, Sanford MS (2006) Tetrahedron 62:2439 CrossRefGoogle Scholar
  39. 39.
    Kalyani D, Deprez NR, Desai LV, Sanford MS (2005) J Am Chem Soc 127:7330 CrossRefGoogle Scholar
  40. 40.
    Henry PM (1971) J Org Chem 36:1886 CrossRefGoogle Scholar
  41. 41.
    Stock LM, Tse K, Vorvick LJ, Walstrum SA (1981) J Org Chem 46:1757 CrossRefGoogle Scholar
  42. 42.
    Eberson L, Jonson L (1974) J Chem Soc Chem Commun 885 Google Scholar
  43. 43.
    Eberson L, Jonson L (1976) Acta Chem Scand B 30:361 CrossRefGoogle Scholar
  44. 44.
    Eberson L, Jonson L (1977) Liebigs Ann Chem 233 Google Scholar
  45. 45.
    Yoneyama T, Crabtree RH (1996) J Mol Catal A 108:35 CrossRefGoogle Scholar
  46. 46.
    Dick AR, Hull KL, Sanford MS (2004) J Am Chem Soc 126:2300 CrossRefGoogle Scholar
  47. 47.
    Kalyani D, Sanford MS (2005) Org Lett 7:4149 CrossRefGoogle Scholar
  48. 48.
    Dick AR, Kampf JW, Sanford MS (2005) Organometallics 24:482 CrossRefGoogle Scholar
  49. 49.
    Schardt BC, Hill CL (1983) Inorg Chem 22:1563 CrossRefGoogle Scholar
  50. 50.
    Desai LV, Hull KL, Sanford MS (2004) J Am Chem Soc 126:9542 CrossRefGoogle Scholar
  51. 51.
    Dangel BD, Johnson JA, Sames D (2001) J Am Chem Soc 123:8149 CrossRefGoogle Scholar
  52. 52.
    Green TW, Wuts PGM (1999) Protective groups in organic synthesis. Wiley, New York CrossRefGoogle Scholar
  53. 53.
    Umino N, Iwakuma T, Ikezaki M, Itoh N (1978) Chem Pharm Bull 26:2897 Google Scholar
  54. 54.
    Kalberer EW, Whitfield SR, Sanford MS (2006) J Mol Catal A 251:108 CrossRefGoogle Scholar
  55. 55.
    Wang D, Hao X, Wu D, Yu J (2006) Org Lett 8:3387 CrossRefGoogle Scholar
  56. 56.
    Desai LV, Malik HA, Sanford MS (2006) Org Lett 8:1141 CrossRefGoogle Scholar
  57. 57.
    Reddy BVS, Reddy LR, Corey EJ (2006) Org Lett 8:3391 CrossRefGoogle Scholar
  58. 58.
    Giri R, Liang J, Lei J, Li J, Wang D, Chen X, Naggar IC, Guo C, Foxman BM, Yu J (2005) Angew Chem Int Ed 44:7420 CrossRefGoogle Scholar
  59. 59.
    Fahey DR (1970) Chem Commun 417 Google Scholar
  60. 60.
    Fahey DR (1971) J Organomet Chem 27:283 CrossRefGoogle Scholar
  61. 61.
    Chen X, Hao X, Goodhue CE, Yu J (2006) J Am Chem Soc 128:6790 CrossRefGoogle Scholar
  62. 62.
    Roy AH, Hartwig JF (2004) Organometallics 23:1533 CrossRefGoogle Scholar
  63. 63.
    Kodama H, Katsuhira T, Nishida T, Hino T, Tsubata K (2001) Chem Abstr 135:344284 Google Scholar
  64. 64.
    Kalyani D, Dick AR, Anani WQ, Sanford MS (2006) Org Lett 8:2523 CrossRefGoogle Scholar
  65. 65.
    Kalyani D, Dick AR, Anani WQ, Sanford MS (2006) Tetrahedron 62:11483 CrossRefGoogle Scholar
  66. 66.
    Wan X, Ma Z, Li B, Zhang K, Cao S, Zhang S, Shi Z (2006) J Am Chem Soc 128:7416 CrossRefGoogle Scholar
  67. 67.
    Giri R, Chen X, Yu J (2005) Angew Chem Int Ed 44:2112 CrossRefGoogle Scholar
  68. 68.
    Giri R, Chen X, Hao X, Li J, Liang J, Fan Z, Yu J (2005) Tetrahedron Asymmetry 16:3502 CrossRefGoogle Scholar
  69. 69.
    Giri R, Wasa M, Breazzano SP, Yu J (2006) Org Lett 8:5685 CrossRefGoogle Scholar
  70. 70.
    Ibrahim H, Togni A (2004) Chem Commun 1147 Google Scholar
  71. 71.
    Hamashima Y, Suzuki T, Takano H, Shimura Y, Sodeoka M (2005) J Am Chem Soc 127:10164 CrossRefGoogle Scholar
  72. 72.
    Hull KL, Anani WQ, Sanford MS (2006) J Am Chem Soc 128:7134 CrossRefGoogle Scholar
  73. 73.
    Grushin VV (2002) Chem Eur J 8:1006 CrossRefGoogle Scholar
  74. 74.
    Tsang WCP, Zheng N, Buchwald SL (2005) J Am Chem Soc 127:14560 CrossRefGoogle Scholar
  75. 75.
    Uemura T, Imoto S, Chatani N (2006) Chem Lett 35:842 CrossRefGoogle Scholar
  76. 76.
    Hartwig JF (2002) Handbook of organopalladium chemistry for organic synthesis. Wiley-Interscience, New York Google Scholar
  77. 77.
    Yang BH, Buchwald SL (1999) J Organomet Chem 576:125 CrossRefGoogle Scholar
  78. 78.
    Thu H, Yu W, Che C (2006) J Am Chem Soc 128:9048 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2007

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of MichiganAnn ArborUSA

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