Cazin, C.  et al.: 2017 Science of Synthesis, 2016/5a: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1 DOI: 10.1055/sos-SD-223-00001
N-Heterocyclic Carbenes in Catalytic Organic Synthesis

1.1.1 Historic Perspectives on Carbenes

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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 provides a brief overview of the historical development of N-heterocyclic carbenes, from inception to isolation of the first stable aminocarbene, followed by the early applications of N-heterocyclic carbene–metal complexes as catalysts.

 
  • 1 Tschugajeff, L, Skanawy-Grigorjewa, M, Posnjak, A. Z. Anorg. Allg. Chem.. 1925; 148: 37
  • 2 In ref 1, the authors mention the following reference as a preliminary communication: Tschugajeff, L. Skanawy-Grigorjewa, M. J. Russ. Chem. Ges. 1915 47 776 This article was subsequently cited as Tschugajeff, L. Skanawy-Grigorjewa, M. J. Russ. Chem. Soc. 1915 47 776 Chugaev, L. Skanavy-Grigorieva, M. J. Russ. Chem. Soc. 1915 47 776 Chugaev, L. Skanavy-Grigorizeva, M. J. Russ. Chem. Soc. 1915 47 776
  • 4 Burke, A, Balch, AL, Enemark, JH. J. Am. Chem. Soc.. 1970; 92: 2555
  • 5 Butler, WM, Enemark, JH, Parks, J, Balch, AL. Inorg. Chem.. 1973; 12: 451
  • 6 Stork, JR, Olmstead, MM, Balch, AL. Inorg. Chem.. 2004; 43: 7508
  • 7 Wanzlick, H.-W, Kleiner, H.-J. Angew. Chem.. 1961; 73: 493
  • 8 Wanzlick, H.-W. Angew. Chem.. 1962; 74: 129 Angew. Chem. Int. Ed. Engl.. 1962; 1: 75
  • 9 Wanzlick, H.-W, Schönherr, H.-J. Angew. Chem.. 1968; 80: 154 Angew. Chem. Int. Ed. Engl.. 1968; 7: 141
  • 11 Cardin, DJ, Çetinkaya, B, Lappert, MF, Manojlović-Muir, , Muir, KW. J. Chem. Soc. D. 1971; 400
  • 12 Cardin, DJ, Çetinkaya, B, Lappert, MF. Chem. Rev.. 1972; 72: 545
  • 14 Igau, A, Grutzmacher, H, Baceiredo, A, Bertrand, G. J. Am. Chem. Soc.. 1988; 110: 6463
  • 15 Arduengo, III AJ, Harlow, RL, Kline, M. J. Am. Chem. Soc.. 1991; 113: 361
  • 16 Herrmann, WA, Elison, M, Fischer, J, Köcher, C, Artus, GRJ. Angew. Chem.. 1995; 107: 2602 Angew. Chem. Int. Ed. Engl.. 1995; 34: 2371
  • 17 N-Heterocyclic Carbenes: Effective Tools for Organometallic Synthesis. Nolan, SP. Ed.. Wiley-VCH; Weinheim, Germany 2014
  • 19 Fortman, GC, Nolan, SP. Chem. Soc. Rev.. 2011; 40: 5151
  • 20 Chartoire, A, Nolan, SP, In New Trends in Cross-Coupling: Theory and Applications. Colacot, TJ. Ed. RSC Cambridge, UK 2014; 139
  • 21 Green, JC, Scurr, RG, Arnold, PL, Cloke, FGN. Chem. Commun. (Cambridge). 1997; 1963
  • 22 Hopkinson, MN, Richter, C, Schedler, M, Glorius, F. Nature (London). 2014; 510: 485; and references cited therein.
  • 23 Trnka, TM, Grubbs, RH. Acc. Chem. Res.. 2001; 34: 18
  • 24 Handbook of Metathesis. Grubbs, RH. Ed.. Wiley-VCH; Weinheim, Germany 2003. 1–3.
  • 25 Huang, J, Stevens, ED, Nolan, SP, Petersen, JL. J. Am. Chem. Soc.. 1999; 121: 2674
  • 26 Scholl, M, Ding, S, Lee, CW, Grubbs, RH. Org. Lett.. 1999; 1: 953
  • 27 Weskamp, T, Kohl, FJ, Herrmann, WA. J. Organomet. Chem.. 1999; 582: 362
  • 28 Vougioukalakis, GC, Grubbs, RH. Chem. Rev.. 2010; 110: 1746
  • 29 Olefin Metathesis: Theory and Practice. Grela, K. Ed.. Wiley; Hoboken, NJ 2014
  • 30 Trimmel, G, Slugovc, C. Monatsh. Chem.. 2015; 146: 1031
  • 31 Bantreil, X, Cazin, CSJ. Monatsh. Chem.. 2015; 146: 1043
  • 32 N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis. Cazin, CSJ. Ed.. Springer; London 2011
  • 33 Marion, N, Díez-González, S, Nolan, SP. Angew. Chem.. 2007; 119: 3046 Angew. Chem. Int. Ed.. 2007; 46: 2988