1.1. 3 Synthesis of N-Heterocyclic Carbenes and Their Precursors
Book
Editors: Cazin, C. ; Nolan, S.
Title: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1
Print ISBN: 9783132012813; Online ISBN: 9783132407633; Book DOI: 10.1055/b-004-132254
1st edition © 2017. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
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.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Type: Multivolume Edition
Abstract
An overview of common methodologies for the preparation of free N-heterocyclic carbenes (NHCs) and their respective precursors is given. In addition to classical five-membered NHCs, examples of less-explored non-classical NHCs, including mesoionic and ring-expanded species, are also described. Experimental procedures reported in the primary literature are included for selected key compounds.
Key words
N-heterocyclic carbenes - carbene dimers - carbene precursors - azolium salts - cyclic thioureas- 7 Rostovtsev, VV, Green, LG, Fokin, VV, Sharpless, KB. Angew. Chem.. 2002; 114: 2708 Angew. Chem. Int. Ed.. 2002; 41: 2596
- 12 Arduengo, III AJ, Krafczyk, R, Schmutzler, R, Craig, HA, Goerlich, JR, Marshall, WJ, Unverzagt, M. Tetrahedron. 1999; 55: 14523
- 13 Thomson, JE, Campbell, CD, Concellón, C, Duguet, N, Rix, K, Slawin, AMZ, Smith, AD. J. Org. Chem.. 2008; 73: 2784
- 15 Iglesias, M, Beetstra, DJ, Stasch, A, Horton, PN, Hursthouse, MB, Coles, SJ, Cavell, KJ, Dervisi, A, Fallis, IA. Organometallics. 2007; 26: 4800
- 16 Bildstein, B, Malaun, M, Kopacka, H, Ongania, K.-H, Wurst, K. J. Organomet. Chem.. 1999; 572: 177
- 24 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
- 26 Otto, M, Conejero, S, Canac, Y, Romanenko, VD, Rudzevitch, V, Bertrand, G. J. Am. Chem. Soc.. 2004; 126: 1016
- 27 Guisado-Barrios, G, Bouffard, J, Donnadieu, B, Bertrand, G. Angew. Chem.. 2010; 122: 4869 Angew. Chem. Int. Ed.. 2010; 49: 4759
- 29 Denk, MK, Thadani, A, Hatano, K, Lough, AJ. Angew. Chem.. 1997; 109: 2719 Angew. Chem. Int. Ed. Engl.. 1997; 36: 2607
- 34 Alder, RW, Blake, ME, Bortolotti, C, Bufali, S, Butts, CP, Linehan, E, Oliva, JM, Orpen, AG, Quayle, MJ. Chem. Commun. (Cambridge). 1999; 241
- 35 Aldeco-Perez, E, Rosenthal, AJ, Donnadieu, B, Parameswaran, P, Frenking, G, Bertrand, G. Science (Washington, D. C.). 2009; 326: 556
- 41 Lavallo, V, Dyker, CA, Donnadieu, B, Bertrand, G. Angew. Chem.. 2008; 120: 5491 Angew. Chem. Int. Ed.. 2008; 47: 5411
- 44 Enders, D, Breuer, K, Raabe, G, Runsink, J, Teles, JH, Melder, J.-P, Ebel, K, Brode, S. Angew. Chem.. 1995; 107: 1119 Angew. Chem. Int. Ed. Engl.. 1995; 34: 1021
- 46 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
- 49 Voutchkova, AM, Feliz, M, Clot, E, Eisenstein, O, Crabtree, RH. J. Am. Chem. Soc.. 2007; 129: 12834
- 50 Azouri, M, Andrieu, J, Picquet, M, Richard, P, Hanquet, B, Tkatchenko, I. Eur. J. Inorg. Chem.. 2007; 4877