Cazin, C.  et al.: 2017 Science of Synthesis, 2016/5a: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1 DOI: 10.1055/sos-SD-223-00028
N-Heterocyclic Carbenes in Catalytic Organic Synthesis

1.1.4 Synthesis of N-Heterocyclic Carbene Complexes

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Book

Editors: Cazin, C. ; Nolan, S.

Authors: Albrecht, M.; Baudrenghien, L.; Bielawski, C.; Biffis, A.; Cavallo, L.; Cazin, C. ; César, V.; Chetcuti, M.; Cuenca, A.; de Frémont, P.; Elie, M.; Fairlamb, I.; Falivene, L.; Fernandez Gutierrez, M. E.; Gagné, M. R.; Gaillard, S.; Huynh, H.; Kalck, P.; Kuwano, R.; Lastovickova, D.; Lavigne, G.; Makida, Y.; Marko, I.; Martin, A.; Nahra, F. ; Nakao, Y.; Ogasawara, M. ; Payne, P.; Renaud, J.; Ronson, T.; Ruamps, M.; Segarra Almela, C.; Teator, A.; Trzeciak, A.; Tubaro, C.; Urrutigoity, M.; Vummaleti, S.; Whittlesey, M.; Yuan, D.

Title: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1

Print ISBN: 9783132012813; Online ISBN: 9783132407633; Book DOI: 10.1055/b-004-132254

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

 


Abstract

This chapter describes the main synthetic pathways to access N-heterocyclic carbene–metal complexes. Routes covered include the complexation of free carbenes, metal-induced decomposition of carbene adducts, in situ generation of carbenes in the presence of metals, transmetalation, and templated synthesis from isocyanides.

 
  • 1 Wanzlick, H.-W, Schönherr, H.-J. Angew. Chem. Int. Ed. Engl.. 1968; 7: 141
  • 4 Arduengo, III AJ, Harlow, RL, Kline, M. J. Am. Chem. Soc.. 1991; 113: 361
  • 5 Herrmann, WA, Elison, M, Fischer, J, Köcher, C, Artus, GRJ. Angew. Chem. Int. Ed. Engl.. 1995; 34: 2371
  • 6 Hudnall, TW, Bielawski, CW. J. Am. Chem. Soc.. 2009; 131: 16039
  • 7 Soleilhavoup, M, Bertrand, G. Acc. Chem. Res.. 2014; 48: 256
  • 8 Lavallo, V, Canac, Y, Präsang, C, Donnadieu, B, Bertrand, G. Angew. Chem. Int. Ed.. 2005; 44: 5705
  • 9 Lavallo, V, Canac, Y, DeHope, A, Donnadieu, B, Bertrand, G. Angew. Chem. Int. Ed.. 2005; 44: 7236
  • 10 Frey, GD, Donnadieu, B, Soleilhavoup, M, Bertrand, G. Chem.–Asian J.. 2011; 6: 402
  • 11 Frey, GD, Dewhurst, RD, Kousar, S, Donnadieu, B, Bertrand, G. J. Organomet. Chem.. 2008; 693: 1674
  • 12 Frey, GD, Masuda, JD, Donnadieu, B, Bertrand, G. Angew. Chem. Int. Ed.. 2010; 49: 9444
  • 13 Trnka, TM, Morgan, JP, Sanford, MS, Wilhelm, TE, Scholl, M, Choi, T.-L, Ding, S, Day, MW, Grubbs, RH. J. Am. Chem. Soc.. 2003; 125: 2546
  • 14 Enders, D, Breuer, K, Raabe, G, Runsink, J, Teles, JH, Melder, J.-P, Ebel, K, Brode, S. Angew. Chem. Int. Ed. Engl.. 1995; 34: 1021
  • 15 Teles, JH, Melder, J.-P, Ebel, K, Schneider, R, Gehrer, E, Harder, W, Brode, S, Enders, D, Breuer, K, Raabe, G. Helv. Chim. Acta. 1996; 79: 61
  • 16 Voutchkova, AM, Appelhans, LN, Chianese, AR, Crabtree, RH. J. Am. Chem. Soc.. 2005; 127: 17624
  • 18 Bellemin-Laponnaz, S, Dagorne, S. Chem. Rev.. 2014; 114: 8747
  • 19 Romain, C, Brelot, L, Bellemin-Laponnaz, S, Dagorne, S. Organometallics. 2010; 29: 1191
  • 20 Romain, C, Heinrich, B, Bellemin-Laponnaz, S, Dagorne, S. Chem. Commun. (Cambridge). 2012; 48: 2213
  • 21 Dagorne, S, Bellemin-Laponnaz, S, Romain, C. Organometallics. 2013; 32: 2736
  • 23 OʼBrien, CJ, Kantchev, EAB, Valente, C, Hadei, N, Chass, GA, Lough, A, Hopkinson, AC, Organ, MG. Chem.–Eur. J.. 2006; 12: 4743
  • 24 Marion, N, Ecarnot, EC, Navarro, O, Amoroso, D, Bell, A, Nolan, SP. J. Org. Chem.. 2006; 71: 3816
  • 26 Kelly, III RA, Scott, NM, Díez-González, S, Stevens, ED, Nolan, SP. Organometallics. 2005; 24: 3442
  • 27 Santoro, O, Collado, A, Slawin, AMZ, Nolan, SP, Cazin, CSJ. Chem. Commun. (Cambridge). 2013; 49: 10483
  • 28 Gibard, C, Ibrahim, H, Gautier, A, Cisnetti, F. Organometallics. 2013; 32: 4279
  • 29 de Frémont, P, Scott, NM, Stevens, ED, Ramnial, T, Lightbody, OC, Macdonald, CLB, Clyburne, JAC, Abernethy, CD, Nolan, SP. Organometallics. 2005; 24: 6301
  • 30 Visbal, R, Laguna, A, Gimeno, MC. Chem. Commun. (Cambridge). 2013; 49: 5642
  • 31 Collado, A, Gómez-Suárez, A, Martin, AR, Slawin, AMZ, Nolan, SP. Chem. Commun. (Cambridge). 2013; 49: 5541
  • 32 Wang, HMJ, Lin, IJB. Organometallics. 1998; 17: 972
  • 33 Lin, JCY, Huang, RTW, Lee, CS, Bhattacharyya, A, Hwang, WS, Lin, IJB. Chem. Rev.. 2009; 109: 3561
  • 34 Larsen, AO, Leu, W, Nieto Oberhuber, C, Campbell, JE, Hoveyda, AH. J. Am. Chem. Soc.. 2004; 126: 11130
  • 35 Van Veldhuizen, JJ, Garber, SB, Kingsbury, JS, Hoveyda, AH. J. Am. Chem. Soc.. 2002; 124: 4954
  • 36 Furst, MRL, Cazin, CSJ. Chem. Commun. (Cambridge). 2010; 46: 6924
  • 37 Michelin, RA, Pombeiro, AJL, Guedes da Silva, MFC. Coord. Chem. Rev.. 2001; 218: 75
  • 38 Riedel, D, Wurm, T, Graf, K, Rudolph, M, Rominger, F, Hashmi, ASK. Adv. Synth. Catal.. 2015; 357: 1515
  • 39 Hashmi, ASK, Yu, Y, Rominger, F. Organometallics. 2012; 31: 895
  • 40 Hashmi, ASK, Lothschütz, C, Graf, K, Häffner, T, Schuster, A, Rominger, F. Adv. Synth. Catal.. 2011; 353: 1407
  • 41 Manzano, R, Rominger, F, Hashmi, ASK. Organometallics. 2013; 32: 2199
  • 42 Hashmi, ASK, Riedel, D, Rudolph, M, Rominger, F, Oeser, T. Chem.–Eur. J.. 2012; 18: 3827
  • 43 Schmidtendorf, M, Pape, T, Hahn, FE. Angew. Chem. Int. Ed.. 2012; 51: 2195