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Transition Metal-Catalyzed Reactions Using N-Heterocyclic Carbene Ligands (Besides Pd- and Ru-Catalyzed Reactions)

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N-Heterocyclic Carbenes in Transition Metal Catalysis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 21))

Abstract

Major advances in transition-metal catalyzed reactions have taken place since the discovery of N-heterocyclic carbenes (NHCs). This review provides a summery of recent M-NHC catalyzed reactions including cycloadditions, rearrangements, coupling reactions, polymerizations, and the additions of H-X.

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References

  1. Hudlicky T, Reed JW (1992) In: Trost BM, Fleming I, Paquette LA (eds) Comprehensive organic synthesis, vol 5. Pergamon, Oxford, pp 899–970

    Google Scholar 

  2. Murakami M, Nishida S (1979) Chem Lett 927

    Google Scholar 

  3. Zuo G, Louie J (2004) Angew Chem Int Ed 43:2777

    Google Scholar 

  4. Wender PA, Barzilay CM, Dyckman AJ (2001) J Am Chem Soc 123:179

    Google Scholar 

  5. Wender PA, Sperandio DA (1998) J Org Chem 63:4164

    Google Scholar 

  6. Wender PA, Takahashi H, Witulski B (1995) J Am Chem Soc 117:4720

    Google Scholar 

  7. Trost BM, Toste FD, Shen H (2000) J Am Chem Soc 122:2379

    Google Scholar 

  8. Zhang M, Buchwald SL (1996) J Org Chem 61:4498

    Google Scholar 

  9. Wender PA, Smith TE (1995) J Org Chem 60:2962

    Google Scholar 

  10. Tamao K, Kobayashi K, Ito Y (1988) J Am Chem Soc 110:1286

    Google Scholar 

  11. Zuo G, Louie J (2005) J Am Chem Soc 127:5798

    Google Scholar 

  12. Inoue Y, Itoh Y, Hashimoto H (1978) Chem Lett 633

    Google Scholar 

  13. Inoue Y, Itoh Y, Hashimoto H (1977) Chem Lett 855

    Google Scholar 

  14. Inoue Y, Itoh Y, Kazama H, Hashimoto H (1980) Bull Chem Soc Jpn 53:3329

    Google Scholar 

  15. Tsuda T, Sumiya R, Saegusa T (1987) Synth Commun 17:147

    Google Scholar 

  16. Tsuda T, Morikawa S, Sumiya R, Saegusa T (1988) J Org Chem 53:3140

    Google Scholar 

  17. Tsuda S, Morikawa S, Saegusa T (1989) J Chem Soc Chem Commun, p 9

    Google Scholar 

  18. Tsuda T, Hasegawa N, Saegusa T (1990) J Chem Soc Chem Commun, p 945

    Google Scholar 

  19. Tsuda T, Morikawa S, Hasegawa N, Saegusa T (1990) J Org Chem 55:2978

    Google Scholar 

  20. Tsuda T, Maruta K, Kitaike T (1992) J Am Chem Soc 114:1498

    Google Scholar 

  21. Louie J, Gibby JE, Farnworth MV, Tekavec TN (2002) J Am Chem Soc 124:15188

    Google Scholar 

  22. Tekavec TN, Arif A, Louie J (2004) Tetrahedron 60:7431

    Google Scholar 

  23. Tsuda T, Kiyoi T, Miyane T, Saegusa T (1988) J Am Chem Soc 110:8570

    Google Scholar 

  24. Tekavec TN, Louie J (2005) Org Lett 7:4037

    Google Scholar 

  25. Miller K, Jamison TF (2005) Org Lett 7:3077

    Google Scholar 

  26. Duong HA, Cross MJ, Louie J (2004) J Am Chem Soc 126:11438

    Google Scholar 

  27. Schössler W, Regitz M (1974) Chem Ber 107:1931

    Google Scholar 

  28. Duong HA, Cross MJ, Louie J (2004) Org Lett 6:4679

    Google Scholar 

  29. Hong P, Yamazaki H (1977) Tetrahedron Lett 1333

    Google Scholar 

  30. Hoberg H, Oster BW (1982) Synthesis 324

    Google Scholar 

  31. Earl RA, Vollhardt KPC (1984) J Org Chem 49:4786

    Google Scholar 

  32. Eisch JJ, Ma X, Han KI, Gitua JN, Krüger C (2001) Eur J Inorg Chem 77

    Google Scholar 

  33. McCormick MM, Duong HA, Zuo G, Louie J (2005) J Am Chem Soc 127:5030

    Google Scholar 

  34. Murakami M, Ashida S, Matsuda T (2005) J Am Chem Soc 127:6932

    Google Scholar 

  35. Eisch JJ, Damasevitz GA (1975) J Organomet Chem 96:C19

    Google Scholar 

  36. Duong HA, Louie J (2005) J Organomet Chem 690:5098

    Google Scholar 

  37. Chan J, Jamison TF (2004) J Am Chem Soc 126:10682

    Google Scholar 

  38. Miller KM, Jamison TF (2005) Org Lett 7:3077

    Google Scholar 

  39. Montgomery J (2000) Acc Chem Res 33:467

    Google Scholar 

  40. Montgomery J (2004) Angew Chem Int Ed 43:3890

    Google Scholar 

  41. Sato Y, Sawaki R, Mori M (2001) Organometallics 20:5510

    Google Scholar 

  42. Sawaki R, Sato Y, Mori M (2004) Org Lett 6:1131

    Google Scholar 

  43. Knapp-Reed B, Mahandru GM, Montgomery J (2005) J Am Chem Soc 127:13156

    Google Scholar 

  44. Ng SS, Jamison TF (2005) J Am Chem Soc 127:7320

    Google Scholar 

  45. Cavell KJ, McGuinness DS (2004) Coord Chem Rev 248:671

    Google Scholar 

  46. McGuinness DS, Mueller W, Wasserscheid P, Cavell KJ, Skelton BW, White AH, Englert U (2002) Organometallics 21:175

    Google Scholar 

  47. Wang X, Liu S, Jin GX (2004) Organometallics 23:6002

    Google Scholar 

  48. Wang X, Liu S, Weng L, Jin GX (2005) J Organomet Chem 690:2934

    Google Scholar 

  49. Louie J, Grubbs RH (2000) Chem Commun 1479

    Google Scholar 

  50. Kuhl S, Schneider R, Fort Y (2003) Organometallics 22:4184

    Google Scholar 

  51. Böhm VPW, Gstöttmayr CWK, Westkamp T, Herrmann WA (2001) Angew Chem Int Ed 40:3387

    Google Scholar 

  52. Blakey SB, MacMillan DWC (2003) J Am Chem Soc 125:6046

    Google Scholar 

  53. Liu J, Robbins MJ (2004) Org Lett 6:3421

    Google Scholar 

  54. Liu J, Robbins MJ (2005) Org Lett 7:1149

    Google Scholar 

  55. McGuinness DS, Cavell KJ, Skelton BW, White AH (1999) Organometallics 18:1596

    Google Scholar 

  56. Chiu PL, Lai CL, Chang CF, Hu CH, Lee HM (2005) Organometallics 24:6169

    Google Scholar 

  57. Inamoto K, Kuroda J, Danjo T, Sakamoto T (2005) Synlett 1624

    Google Scholar 

  58. Gradel B, Brenner E, Schneider R, Fort Y (2001) Tetrahedron Lett 42:5689

    Google Scholar 

  59. Desmarets C, Schneider R, Fort Y (2002) J Org Chem 67:3029

    Google Scholar 

  60. Omar-Amrani R, Thomas A, Brenner E, Schneider R, Fort Y (2003) Org Lett 5:2311

    Google Scholar 

  61. Kelly RA III, Scott NM, Díez-González S, Stevens ED, Nolan SP (2005) Organometallics 24:3442

    Google Scholar 

  62. Fraser PK, Woodward S (2001) Tetrahedron Lett 42:2747

    Google Scholar 

  63. Guillen F, Winn CL, Alexakis A (2001) Tetrahedron Asymmetry 12:2083

    Google Scholar 

  64. Pytkowicz J, Roland S, Mangeney P (2001) Tetrahedron Asymmetry 12:2087

    Google Scholar 

  65. Alexakis A, Winn CL, Guillen F, Pytkowicz J, Roland S, Mangeney P (2003) Adv Synth Catal 345

    Google Scholar 

  66. Clavier H, Coutable L, Toupet L, Guillemin J, Mauduit M (2005) J Organomet Chem 690:5237

    Google Scholar 

  67. Lee HM, Jiang T, Stevens ED, Nolan SP (2001) Organometallics 20:1255

    Google Scholar 

  68. Powell MT, Hou D, Perry MC, Cui X, Burgess K (2001) J Am Chem Soc 123:8878

    Google Scholar 

  69. Perry MC, Cui X, Hou D, Reibenspies JH (2003) J Am Chem Soc 125:113

    Google Scholar 

  70. Albrecht M, Crabtree RH, Mata J, Peris E (2002) J Chem Soc Chem Commun 32

    Google Scholar 

  71. Albrecht M, Miecznikowski JR, Samuel A, Faller JW, Crabtree RH (2002) Organometallics 21:3596

    Google Scholar 

  72. Miecznikowski JR, Crabtree RH (2004) Organometallics 24:629

    Google Scholar 

  73. Hiller AC, Lee HM, Stevens ED, Nolan SP (2001) Organometallics 20:4246

    Google Scholar 

  74. Mas-Marzá E, Poyatos M, Sanaú M, Peris E (2004) Organometallics 23:323

    Google Scholar 

  75. Lappert MF, Maskell RK (1984) J Organomet Chem 264:217

    Google Scholar 

  76. Imlinger N, Wurst K, Buchmeiser MR (2005) J Organomet Chem 690:4433

    Google Scholar 

  77. Mas-Marzá E, Poyatos M, Sanaú M, Peris E (2004) Inorg Chem 43:2213

    Google Scholar 

  78. Enders D, Gielen H, Breuer K (1997) Tetrahedron Asymmetry 8:3571

    Google Scholar 

  79. Enders D, Gielen H (2001) J Organomet Chem 617

    Google Scholar 

  80. Gade LH, César V, Bellemin-Laponnaz S (2004) Angew Chem Int Ed 43:1014

    Google Scholar 

  81. Duan W, Shi M, Rong G (2002) J Chem Soc Chem Commun 2916

    Google Scholar 

  82. Chianese AR, Crabtree RH (2005) Organometallics 24:4432

    Google Scholar 

  83. Burling S, Field LD, Li HL, Messerle BA, Turner P (2003) Eur J Inorg Chem 3179

    Google Scholar 

  84. Field LD, Messerle BA, Vuong KQ, Turner P (2005) Organometallics 24:4241

    Google Scholar 

  85. Chen AC, Ren L, Decken A, Crudden CM (2000) Organometallics 19:3459

    Google Scholar 

  86. Poyatos M, Uriz P, Mata JA, Claver C, Fernandez E, Peris E (2003) Organometallics 22:440

    Google Scholar 

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Correspondence to Janis Louie .

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Tekavec, T.N., Louie, J. (2006). Transition Metal-Catalyzed Reactions Using N-Heterocyclic Carbene Ligands (Besides Pd- and Ru-Catalyzed Reactions). In: N-Heterocyclic Carbenes in Transition Metal Catalysis. Topics in Organometallic Chemistry, vol 21. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-36930-1_6

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