Cazin, C. S. J. et al.: 2017 Science of Synthesis, 2016/5a: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1 DOI: 10.1055/sos-SD-223-00003
N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1

1.1.2 Types of N-Heterocyclic Carbenes

More Information

Book

Editors: Cazin, C. S. J.; Nolan, S. P.

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

Science of Synthesis Reference Libraries



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. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

 


Abstract

This chapter discusses the different types of N-heterocyclic carbenes (NHCs) and is organized according to ring size. The terminology for describing NHCs as normal or abnormal (mesoionic) and remote or nonremote is outlined. The pertinent properties of these different NHCs are compiled, in particular the 13C NMR spectroscopic and crystallographic parameters, as well as steric and electronic effects, which provides insights into the donor properties of the various classes of NHCs.

 
  • 4 Kuhn N, Kratz T. Synthesis 1993; 561
  • 5 Arduengo III AJ, Bock H, Chen H, Denk M, Dixon DA, Green JC, Herrmann WA, Jones NL, Wagner M, West R. J. Am. Chem. Soc. 1994; 116: 6641
  • 6 Arduengo III AJ, Dias HVR, Dixon DA, Harlow RL, Klooster WT, Koetzle TF. J. Am. Chem. Soc. 1994; 116: 6812
  • 8 Arduengo III AJ, Davidson F, Dias HVR, Goerlich JR, Khasnis D, Marshall WJ, Prakasha TK. J. Am. Chem. Soc. 1997; 119: 12742
  • 9 Arduengo III AJ, Goerlich JR, Krafczyk R, Marshall WJ. Angew. Chem. Int. Ed. 1998; 37: 1963
  • 10 Arduengo III AJ, Krafczyk R, Schmutzler R, Craig HA, Goerlich JR, Marshall WJ, Unverzagt M. Tetrahedron 1999; 55: 14523
  • 11 Niehues M, Kehr G, Erker G, Wibbeling B, Fröhlich R, Blacque O, Berke H. J. Organomet. Chem. 2002; 663: 192
  • 12 Saravanakumar S, Kindermann MK, Heinicke J, Köckerling M. Chem. Commun. (Cambridge) 2006; 640
  • 15 Iglesias M, Beetstra DJ, Knight JC, Ooi L.-L, Stasch A, Coles S, Male L, Hursthouse MB, Cavell KJ, Dervisi A, Fallis IA. Organometallics 2008; 27: 3279
  • 17 Korotkikh NI, Raenko GF, Pekhtereva TM, Shvaika OP, Cowley AH, Jones JN. Russ. J. Org. Chem. (Engl. Transl.) 2006; 42: 1822
  • 18 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
  • 19 Korotkikh NI, Rayenko GF, Shvaika OP, Pekhtereva TM, Cowley AH, Jones JN, Macdonald CLB. J. Org. Chem. 2003; 68: 5762
  • 23 Gründemann S, Kovacevic A, Albrecht M, Faller JW, Crabtree RH. Chem. Commun. (Cambridge) 2001; 2274
  • 29 Meyer WH, Deetlefs M, Pohlmann M, Scholz R, Esterhuysen MW, Julius GR, Raubenheimer HG. Dalton Trans. 2004; 413
  • 30 Schneider SK, Julius GR, Loschen C, Raubenheimer HG, Frenking G, Herrmann WA. Dalton Trans. 2006; 1226
  • 33 Calò V, Del Sole R, Nacci A, Schingaro E, Scordari F. Eur. J. Org. Chem. 2000; 869
  • 35 Fränkel R, Kernbach U, Bakola-Christianopoulou M, Plaia U, Suter M, Ponikwar W, Nöth H, Moinet C, Fehlhammer WP. J. Organomet. Chem. 2001; 617: 530
  • 37 Back O, Henry-Ellinger M, Martin CD, Martin D, Bertrand G. Angew. Chem. Int. Ed. 2013; 52: 2939
  • 43 Albrecht M. Chem. Commun. (Cambridge) 2008; 3601
  • 46 Aldeco-Perez E, Rosenthal AJ, Donnadieu B, Parameswaran P, Frenking G, Bertrand G. Science (Washington, D. C.) 2009; 326: 556
  • 47 Lewis WG, Green LG, Grynszpan F, Radić Z, Carlier PR, Taylor P, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 1053
  • 48 Guisado-Barrios G, Bouffard J, Donnadieu B, Bertrand G. Angew. Chem. Int. Ed. 2010; 49: 4759
  • 49 Bouffard J, Keitz BK, Tonner R, Guisado-Barrios G, Frenking G, Grubbs RH, Bertrand G. Organometallics 2011; 30: 2617
  • 51 Kelly III RA, Clavier H, Giudice S, Scott NM, Stevens ED, Bordner J, Samardjiev I, Hoff CD, Cavallo L, Nolan SP. Organometallics 2008; 27: 202
  • 53 Han Y, Huynh HV. Chem. Commun. (Cambridge) 2007; 1089
  • 56 Anderson DR, Ung T, Mkrtumyan G, Bertrand G, Grubbs RH, Schrodi Y. Organometallics 2008; 27: 563
  • 59 Alder RW, Blake ME, Bortolotti C, Bufali S, Butts CP, Linehan E, Oliva JM, Orpen AG, Quayle MJ. Chem. Commun. (Cambridge) 1999; 241
  • 60 Yasui M, Yoshida S, Kakuma S, Shimamoto S, Matsumura N, Iwasaki F. Bull. Chem. Soc. Jpn. 1996; 69: 2739
  • 61 Otto M, Conejero S, Canac Y, Romanenko VD, Rudzevitch V, Bertrand G. J. Am. Chem. Soc. 2004; 126: 1016
  • 63 Fraser PJ, Roper WR, Stone FGA. J. Chem. Soc., Dalton Trans. 1974; 760
  • 64 Lavorato D, Terlouw JK, Dargel TK, Koch W, McGibbon GA, Schwarz H. J. Am. Chem. Soc. 1996; 118: 11898
  • 65 Lalrempuia R, McDaniel ND, Müller-Bunz H, Bernhard S, Albrecht M. Angew. Chem. Int. Ed. 2010; 49: 9765
  • 66 Iglesias M, Beetstra DJ, Stasch A, Horton PN, Hursthouse MB, Coles SJ, Cavell KJ, Dervisi A, Fallis IA. Organometallics 2007; 26: 4800