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N-Heterocyclic Carbene Complexes in Additions to Multiple Bonds

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N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 32))

Abstract

The use of N-heterocyclic carbene (NHC) complexes as homogeneous catalysts in addition reactions across carbon-carbon double and triple bonds and carbon-heteroatom double bonds is described. The discussion is focused on the description of the catalytic systems, their current mechanistic understanding and occasionally the relevant organometallic chemistry. The reaction types covered include hydrogenation, transfer hydrogenation, hydrosilylation, hydroboration and diboration, hydroamination, hydrothiolation, hydration, hydroarylation, allylic substitution, addition, chloroesterification and chloroacylation.

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References

  1. Praetorius JM, Wang R, Crudden CM (2009) Eur J Inorg Chem 13:1746–1751

    Google Scholar 

  2. Yu X-Y, Sun H, Brian PO, James BR (2009) Eur J Inorg Chem 13:1752–1758

    Google Scholar 

  3. Huang J, Stevens ED, Nolan SP (2000) Organometallics 19:1194–1197

    CAS  Google Scholar 

  4. Hillier AC, Lee HM, Stevens ED, Nolan SP (2001) Organometallics 20:4246–4252

    CAS  Google Scholar 

  5. Herrmann WA, Frey GD, Herdtweck E, Steinbeck M (2007) Adv Synth Catal 349:1677–1691

    CAS  Google Scholar 

  6. Allen DP, Crudden CM, Calhoun LA, Wang R, Decken A (2005) J Organomet Chem 690:5736–5746

    CAS  Google Scholar 

  7. Baskakov D, Herrmann WA, Herdtweck E, Hoffmann SD (2007) Organometallics 26:626–632

    CAS  Google Scholar 

  8. Herrmann WA, Baskakov D, Herdtweck E, Hoffmann SD, Bunlaksananusorn T, Rampf F, Rodefeld L (2006) Organometallics 25:2449–2456

    CAS  Google Scholar 

  9. Lee HM, Smith DC Jr, He Z, Stevens ED, Yi CS, Nolan SP (2001) Organometallics 20:794–797

    CAS  Google Scholar 

  10. Dinger MB, Mol JC (2003) Eur J Inorg Chem 2827–2833

    Google Scholar 

  11. Dharmasena UL, Foucault HM, dos Santos EN, Fogg DE, Nolan SP (2005) Organometallics 24:1056–1058

    CAS  Google Scholar 

  12. Grasa GA, Moore Z, Martin KL, Stevens ED, Nolan SP, Paquet V, Lebel HJ (2002) J Organomet Chem 658:126–131

    CAS  Google Scholar 

  13. Jazzar RFR, Macgregor SA, Mahon MF, Richards SP, Whittlesey MK (2002) J Am Chem Soc 124:4944–4945

    CAS  Google Scholar 

  14. Edwards MG, Jazzar RFR, Paine BM, Shermer DJ, Whittlesey MK, Williams JMJ, Edney DD (2004) Chem Commun 90–91

    Google Scholar 

  15. Chantler VL, Chatwin SL, Jazzar RFR, Mahon MF, Saker O, Whittlesey MK (2008) Dalton Trans 2603–2614

    Google Scholar 

  16. Vazquez-Serrano LD, Owens BT, Buriak JM (2002) Chem Commun 2518–2519

    Google Scholar 

  17. Sprengers JW, Wassenaar J, Clement ND, Cavell KJ, Elsevier CJ (2005) Angew Chem Int Ed 44:2026–2029

    CAS  Google Scholar 

  18. Jurcik V, Nolan SP, Cazin CSJ (2009) Chem Eur J 15:2509–2511

    CAS  Google Scholar 

  19. Heckenroth M, Kluser E, Neels A, Albrecht M (2007) Angew Chem Int Ed 46:6293–6296

    CAS  Google Scholar 

  20. Nanchen S, Pfaltz A (2006) Chem Eur J 12:4550–4558

    CAS  Google Scholar 

  21. Powell MT, Hou DR, Perry MC, Cui X, Burgess K (2001) J Am Chem Soc 123:8878–8879

    CAS  Google Scholar 

  22. Gunther, H (2004) Synlett 1789–1793

    Google Scholar 

  23. Perry MC, Cui X, Powell MT, Hou DR, Reibenspies JH, Burgess K (2003) J Am Chem Soc 125:113–123

    CAS  Google Scholar 

  24. Fan Y, Cui X, Burgess K, Hall B (2004) J Am Chem Soc 126:16688–16689

    CAS  Google Scholar 

  25. Corma A, Puebla-Gutierrez E, Iglesias M, Monge A, Perez-Ferreras S, Sanchez F (2006) Adv Synth Catal 348:1899–1907

    CAS  Google Scholar 

  26. Hillier AC, Lee HM, Stevens ED, Nolan SP (2001) Organometallics 20:4246–4252

    CAS  Google Scholar 

  27. Gnanamgari D, Moores A, Rajaseelan E, Crabtree RH (2007) Organometallics 26:1226–1230

    CAS  Google Scholar 

  28. Gnanamgari D, Sauer ELO, Schley ND, Butler C, Incarvito CD, Crabtree RH (2009) Organometallics 28:321–325

    CAS  Google Scholar 

  29. Danopoulos AA, Winston S, Motherwell WB (2002) Chem Commun 1376–1377

    Google Scholar 

  30. Peris E, Mata JA, Crabtree RH, Poyatos M (2003) Organometallics 22:1110–1114

    Google Scholar 

  31. Crabtree RH, Faller JW (2002) Organometallics 21:3596–3604

    Google Scholar 

  32. Peris E, Mas-Marza E, Sanau M (2005) Inorg Chem 44:9961–9967

    Google Scholar 

  33. Stylianides N, Danopoulos AA, Tsoureas N (2005) J Organomet Chem 690:5948–5958

    CAS  Google Scholar 

  34. Wang CY, Fu CF, Liu YH, Peng SM, Liu ST (2007) Inorg Chem 46:5779–5786

    CAS  Google Scholar 

  35. Turkmen H, Pape T, Hahn FE, Cetinkaya B (2008) Eur J Inorg Chem 5418–5423

    Google Scholar 

  36. Yang L, Kruger A, Neels A, Albrecht M (2008) Organometallics 27:3161–3171

    CAS  Google Scholar 

  37. Danopoulos AA, Fiddy SG, Evans J, Neisius T, Newton MA, Tsoureas N, Tulloch AAD (2007) Chem Eur J 13:3652–3659

    Google Scholar 

  38. Miecznikowski JR, Crabtree RH (2004) Organometallics 23:629–631

    CAS  Google Scholar 

  39. Kuhl S, Schneider R, Fort Y (2003) Organometallics 22:4184–4186

    CAS  Google Scholar 

  40. Peris E, da Costa AP, Viciano M, Sanau M, Merino S, Tejeda J, Royo B (2008) Organometallics 27:1305–1309

    Google Scholar 

  41. Guillena G, Ramon DJ, Yus M (2007) Angew Chem Int Ed 46:2358–2364

    CAS  Google Scholar 

  42. Crabtree RH, Faller JW (2002) Organometallics 21:3596–3604

    Google Scholar 

  43. Castarlenas R, Esteruelas MA, Onate E (2008) Organometallics 27:3240–3247

    CAS  Google Scholar 

  44. Berthon-Gelloz G, Buisine O, Briere JF, Michaud G, Sterin S, Mignani G, Tinant B, Declercq JP, Chapon D, Marko IE (2005) J Organomet Chem 690:6156–6168

    CAS  Google Scholar 

  45. Sprengers JW, Mars MJ, Duin MA, Cavell KJ, Elsevier CJ (2003) J Organomet Chem 679:149–152

    CAS  Google Scholar 

  46. De Bo G, Berthon-Gelloz G, Tinant B, Marko IE (2006) Organometallics 25:1881–1890

    Google Scholar 

  47. Poyatos M, Mas-Marza E, Mata JA, Sanau M, Peris E (2003) Eur J Inorg Chem 1215–1221

    Google Scholar 

  48. Mas-Marza E, Sanau M, Peris E (2005) Inorg Chem 44:9961–9967

    CAS  Google Scholar 

  49. Jimenez MV, Perez-Torrente JJ, Bartolome MI, Gierz V, Lahoz FJ, Oro LA (2008) Organometallics 27:224–234

    CAS  Google Scholar 

  50. Chaulagain MR, Mahandru GM, Montgomery J (2006) Tetrahedron 62:7560–7566

    CAS  Google Scholar 

  51. Díez-González S, Nolan SP (2008) Acc Chem Res 41:349–358

    Google Scholar 

  52. Díez-González S, Scott NM, Nolan SP (2006) Organometallics 25:2355–2358

    Google Scholar 

  53. Kaur H, Zinn FK, Stevens ED, Nolan SP (2004) Organometallics 23:1157–1160

    CAS  Google Scholar 

  54. Díez-González S, Stevens ED, Scott NM, Petersen JL, Nolan SP (2008) Chem Eur J 14:158–168

    Google Scholar 

  55. Faller JW, Fontaine P (2006) Organometallics 25:5887–5893

    CAS  Google Scholar 

  56. Cesar V, Bellemin-Laponnaz S, Wadepohl H, Gade LH (2005) Chem Eur J 11:2862–2873

    CAS  Google Scholar 

  57. Schneider N, Kruck M, Bellemin-Laponnaz S, Wadepohl H, Gade LH (2009) Eur J Inorg Chem 493–500

    Google Scholar 

  58. Thomas RL, Souza FES, Marder TB (2001) J Chem Soc Dalton Trans 1650–1656

    Google Scholar 

  59. Mann G, John KD, Baker RT (2000) Org Lett 2:2105–2108

    CAS  Google Scholar 

  60. Baker RT, Nguyen P, Marder TB, Westcott SA (1995) Angew Chem Int Ed 34:1336–1338

    CAS  Google Scholar 

  61. Dai C, Robins EG, Scott AJ, Clegg W, Yufit DS, Howard JAK, Marder TB (1998) Chem Commun 1983–1984

    Google Scholar 

  62. Ramirez J, Corberan R, Sanau M, Peris E, Fernandez E (2005) Chem Commun 3056–3058

    Google Scholar 

  63. Corberan R, Ramirez J, Poyatos M, Peris E, Fernandez E (2006) Tetrahedron Asymm 17:1759–1762

    CAS  Google Scholar 

  64. Lillo V, Mata J, Ramirez J, Peris E, Fernandez E (2006) Organometallics 25:5829–5831

    CAS  Google Scholar 

  65. Lillo V, Mas-Marza E, Segarra AM, Carbo JJ, Bo C, Peris E, Fernandez E (2007) Chem Commun 3380–3382

    Google Scholar 

  66. Peris E, Corberan R, Lillo V, Mata J, Fernandez E (2007) Organometallics 26:4350–4353

    Google Scholar 

  67. Laitar DS, Tsui EY, Sadighi JP (2006) Organometallics 25:2405–2408

    CAS  Google Scholar 

  68. Lillo V, Fructos MR, Ramirez JB, Maseras F, Diaz-Requejo MM, Perez PJ, Fernandez E (2007) Chem Eur J 13:2614–2621

    CAS  Google Scholar 

  69. Lillo V, Mata JA, Segarra AM, Peris E, Fernandez E (2007) Chem Commun 2184–2186

    Google Scholar 

  70. Khramov DM, Rosen EL, Vu PD, Lynch VM, Bielawski CW (2008) Tetrahedron 64:6853–6862

    CAS  Google Scholar 

  71. Lee Y, Hoveyda AH (2009) J Am Chem Soc 131:3160–3161

    CAS  Google Scholar 

  72. Beller M, Seayad J, Tillack A, Jiao H (2004) Angew Chem Int Ed 43:3368–3398

    CAS  Google Scholar 

  73. Muller TE, Yus M, Mizuki T (2008) Chem Rev 108:3795–3892

    Google Scholar 

  74. Takaki K, Koizumi S, Yamamoto Y, Komeyama K (2007) Tetrahedron Lett 48:4643–4644

    CAS  Google Scholar 

  75. Field LD, Messerle BA, Vuong KQ, Turner P (2005) Organometallics 24:4241–4250

    CAS  Google Scholar 

  76. Burling S, Field LD, Li HL, Messerle BA, Turner P (2003) Eur J Inorg Chem 3179–3184

    Google Scholar 

  77. Bauer EB, Andavan GTS, Hollis TK, Rubio RJ, Cho J, Kuchenbeiser GR, Helgert TR, Letko CS, Tham FS (2008) Org Lett 10:1175–1178

    CAS  Google Scholar 

  78. Cho J, Hollis TK, Helgert TR, Valente EJ (2008) Chem Commun 5001–5003

    Google Scholar 

  79. Gischig S, Togni A (2005) Eur J Inorg Chem 4745–4754

    Google Scholar 

  80. Houghton J, Dyson G, Douthwaite RE, Whitwood AC, Kariuki BM (2007) Dalton Trans 3065–3073

    Google Scholar 

  81. Munro-Leighton C, Delp SA, Blue ED, Gunnoe TB (2007) Organometallics 26:1483–1493

    CAS  Google Scholar 

  82. Munro-Leighton C, Delp SA, Alsop NM, Blue ED, Gunnoe TB (2008) Chem Commun 111–113

    Google Scholar 

  83. Kinder RE, Zhang Z, Widenhoefer RA (2008) Org Lett 10:3157–3159

    CAS  Google Scholar 

  84. Malyshev DA, Scott NM, Marion N, Stevens ED, Ananikov VP, Beletskaya IP, Nolan SP (2006) Organometallics 25:4462–4470

    CAS  Google Scholar 

  85. Delp SA, Munro-Leighton C, Goj LA, Ramirez MA, Gunnoe TB, Petersen JL, Boyle PD (2007) Inorg Chem 46:2365–2367

    CAS  Google Scholar 

  86. Zhang Z, Widenhoefer RA (2008) Org Lett 10:2079–2081

    CAS  Google Scholar 

  87. Marion N, Ramon RS, Nolan SP (2009) J Am Chem Soc 13:448–449

    Google Scholar 

  88. De Fremont P, Singh R, Stevens ED, Petersen JL, Nolan SP (2007) Organometallics 26:1376–1385

    Google Scholar 

  89. Zhang Z, Du Lee S, Fisher AS, Widenhoefer RA (2009) Tetrahedron 65:1794–1798

    CAS  Google Scholar 

  90. Viciu MS, Stevens ED, Petersen JL, Nolan SP (2004) Organometallics 23:3752–3755

    CAS  Google Scholar 

  91. Biffis A, Tubaro C, Buscemi G, Basato M (2008) Adv Synth Catal 350:189–196

    CAS  Google Scholar 

  92. Marion N, Diez-Gonzalez S, de Fremont P, Noble AR, Nolan SP (2006) Angew Chem Int Ed 45:3647–3650

    CAS  Google Scholar 

  93. Sato Y, Yoshin T, Mori M (2003) Org Lett 31–33

    Google Scholar 

  94. Sato Y, Yoshino T, Mori M (2005) J Organomet Chem 690:5753–5758

    CAS  Google Scholar 

  95. Visentin F, Togni A (2007) Organometallics 26:3746–3754

    CAS  Google Scholar 

  96. Rosenblade SJ, Ros A, Monge D, Alcarazo M, Alvarez E, Lassaletta JM, Fernandez R (2007) Organometallics 26:2570–2578

    Google Scholar 

  97. Bonnet LG, Douthwaite RE, Kariuki BM (2003) Organometallics 22:4187–4189

    CAS  Google Scholar 

  98. Toselli N, Martin D, Buono G (2008) Org Lett 10:1453–1456

    CAS  Google Scholar 

  99. Lee K, Brown MK, Hird AW, Hoveyda AH (2006) J Am Chem Soc 128:7182–7184

    CAS  Google Scholar 

  100. Van Veldhuizen JJ, Campbell JE, Giudici RE, Hoveyda AH (2005) J Am Chem Soc 127:6877–6882

    Google Scholar 

  101. Lee Y, Akiyama K, Gillingham DG, Brown MK, Hoveyda AH (2008) J Am Chem Soc 130:446–447

    CAS  Google Scholar 

  102. Yasar S, Ozdemir I, Cetinkaya B, Renaud JL, Bruneau C (2008) Eur J Org Chem 2142–2149

    Google Scholar 

  103. Plietker B, Dieskau A, Moews K, Jatsch A (2008) Angew Chem Int Ed 47:198–201

    CAS  Google Scholar 

  104. Barczak NT, Grote RE, Jarvo ER (2007) Organometallics 26:4863–4865

    CAS  Google Scholar 

  105. Fraser PK, Woodward S (2001) Tetrahedron Lett 42:2747–2749

    CAS  Google Scholar 

  106. Winn CL, Guillen F, Pytkowicz J, Roland S, Mangeney P, Alexakis A (2005) J Organomet Chem 690:5672–5695

    CAS  Google Scholar 

  107. Arnold PL, Rodden M, Davis KM, Scarisbrick AG, Blake AJ, Wilson C (2004) Chem Commun 1612–1613

    Google Scholar 

  108. Clavier H, Coutable L, Toupet L, Guillemin J-C, Mauduit M (2005) J Organomet Chem 690:5237–5254

    CAS  Google Scholar 

  109. Lee K, Hoveyda AH (2009) J Org Chem 74:4455–4462

    CAS  Google Scholar 

  110. Lee K, Brown MK, Hird AW, Hoveyda AH (2006) J Am Chem Soc 128:7183–7184

    Google Scholar 

  111. Martin D, Kehrli S, d’Augustin M, Clavier H, Mauduit M, Alexakis A (2006) J Am Chem Soc 128:8416–8417

    CAS  Google Scholar 

  112. Matsumoto Y, Yamada K, Tomioka K (2008) J Org Chem 73:4578–4581

    CAS  Google Scholar 

  113. Zhang T, Shi M (2008) Chem Eur J 14:3759–3764

    CAS  Google Scholar 

  114. Lillo V, Prieto A, Bonet A, Diaz-Requejo MM, Ramirez J, Perez PJ, Fernandez E (2009) Organometallics 28:659–662

    CAS  Google Scholar 

  115. Hua R, Shimada S, Tanaka M (1998) J Am Chem Soc 120:12365–12366

    CAS  Google Scholar 

  116. Sim H, Baek JY (2008) Synlett 551–554

    Google Scholar 

  117. Iwai T, Fujihara T, Terao J, Tsuji Y (2009) J Am Chem Soc 131:6668–6669

    CAS  Google Scholar 

  118. For a recent review on Late Transition Metal-NHC complexes and catalysis see: Díez-González S, Marion N, Nolan SP (2009) Chem Rev 109:3612–3676

    Google Scholar 

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Correspondence to Andreas A. Danopoulos .

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Danopoulos, A.A. (2010). N-Heterocyclic Carbene Complexes in Additions to Multiple Bonds. In: Cazin, C. (eds) N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis. Catalysis by Metal Complexes, vol 32. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-2866-2_2

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