Download PDF
Cazin, C.  et al.: 2018 Science of Synthesis, 2016/5b: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2 DOI: 10.1055/sos-SD-224-00001
N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2

2.1.1 Historical Overview of N-Heterocyclic Carbenes in Alkene Metathesis

More Information

Book

Editors: Cazin, C. ; Nolan, S.

Authors: Basle, O.; Broggi, J.; Claver, C.; Clavier, H.; Collins, S. K.; Costabile, C.; Crevisy, C.; Crozet, D.; Davies, A.; Diesendruck, C. E.; Felten, S.; Godard, C.; Grela, K.; Holtz-Mulholland, M.; Jana, A.; Johnson, J.; Lapkin, A.; Liu, J.; Lombardía, A.; Louie, J.; Malecki, P.; Mauduit, M.; Munz, D.; Nelson, D.; Peñafiel, I.; Schmid, T.; Slugovc, C.; Smith, A. D.; Thieuleux, C.; Zhong, Y.

Title: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2

Print ISBN: 9783132414006; Online ISBN: 9783132414044; Book DOI: 10.1055/b-004-140260

1st edition © 2018 Georg Thieme Verlag KG
Georg Thieme Verlag, 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

Also available at
 


Abstract

This chapter is a short outline of the historic development of the use of N-heterocyclic carbenes as co-ligands in alkene metathesis catalysts.

Key words

alkene metathesis - N-heterocyclic carbenes - alkenes - ruthenium - molybdenum
 
  • 1 Nguyen ST, Johnson LK, Grubbs RH, Ziller JW. J. Am. Chem. Soc. 1992; 114: 3974
  • 2 Trnka TM, Grubbs RH. Acc. Chem. Res. 2001; 34: 18
  • 3 Schwab P, France MB, Ziller JW, Grubbs RH. Angew. Chem. Int. Ed. Engl. 1995; 34: 2039
  • 4 Dias EL, Nguyen ST, Grubbs RH. J. Am. Chem. Soc. 1997; 119: 3887
  • 5 Herrmann WA, Elison M, Fischer J, Köcher C, Artus GRJ. Chem.–Eur. J. 1996; 2: 772
  • 6 Herrmann WA, Schattenmann WC, Weskamp T. DE 19 815 275 A1, 1999
  • 7 Weskamp T, Schattenmann WC, Spiegler M, Herrmann WA. Angew. Chem. Int. Ed. 1998; 37: 2490
  • 8 Huang J, Stevens ED, Nolan SP, Petersen JL. J. Am. Chem. Soc. 1999; 121: 2674
  • 9 Scholl M, Trnka TM, Morgan JP, Grubbs RH. Tetrahedron Lett. 1999; 40: 2247
  • 10 Weskamp T, Kohl FJ, Herrmann WA. J. Organomet. Chem. 1999; 582: 362
  • 11 Ulman M, Grubbs RH. J. Org. Chem. 1999; 64: 7202
  • 12 Jafarpour L, Huang J, Stevens ED, Nolan SP. Organometallics 1999; 18: 3760
  • 13 Jafarpour L, Schanz H.-J, Stevens ED, Nolan SP. Organometallics 1999; 18: 5416
  • 14 Scholl M, Ding S, Lee CW, Grubbs RH. Org. Lett. 1999; 1: 953
  • 15 Garber SB, Kingsbury JS, Gray BL, Hoveyda AH. J. Am. Chem. Soc. 2000; 122: 8168
  • 16 Gessler S, Randl S, Blechert S. Tetrahedron Lett. 2000; 41: 9973
  • 17 Randl S, Gessler S, Wakamatsu H, Blechert S. Synlett 2001; 430
  • 18 Ahmed M, Arnauld T, Barrett AGM, Braddock DC, Procopiou PA. Synlett 2000; 1007
  • 19 Jafarpour L, Nolan SP. Org. Lett. 2000; 2: 4075
  • 20 Schürer SC, Gessler S, Buschmann N, Blechert S. Angew. Chem. Int. Ed. 2000; 39: 3898
  • 21 Ackermann L, Fürstner A, Weskamp T, Kohl FJ, Herrmann WA. Tetrahedron Lett. 1999; 40: 4787
  • 22 Chatterjee AK, Grubbs RH. Org. Lett. 1999; 1: 1751
  • 23 Morgan JP, Grubbs RH. Org. Lett. 2000; 2: 3153
  • 24 Fürstner A, Thiel OR, Ackermann L, Schanz H.-J, Nolan SP. J. Org. Chem. 2000; 65: 2204
  • 25 Sanford MS, Love JA, Grubbs RH. J. Am. Chem. Soc. 2001; 123: 6543
  • 26 Cavallo L. J. Am. Chem. Soc. 2002; 124: 8965
  • 27 Louie J, Bielawski CW, Grubbs RH. J. Am. Chem. Soc. 2001; 123: 11312
  • 28 Sanford MS, Love JA, Grubbs RH. Organometallics 2001; 20: 5314
  • 29 Fürstner A, Krause H, Ackermann L, Lehmann CW. Chem. Commun. (Cambridge) 2001; 2240
  • 30 Seiders TJ, Ward DW, Grubbs RH. Org. Lett. 2001; 3: 3225
  • 31 Wakamatsu H, Blechert S. Angew. Chem. Int. Ed. 2002; 41: 2403
  • 32 Grela K, Harutyunyan S, Michrowska A. Angew. Chem. Int. Ed. 2002; 41: 4038
  • 33 Slugovc C, Demel S, Stelzer F. Chem. Commun. (Cambridge) 2002; 2572
  • 34 Choi T.-L, Grubbs RH. Angew. Chem. Int. Ed. 2003; 42: 1743
  • 35 Bielawski CW, Benitez D, Grubbs RH. Science (Washington, D. C.) 2002; 297: 2041
  • 36 Sutton AE, Seigal BA, Finnegan DF, Snapper ML. J. Am. Chem. Soc. 2002; 124: 13390
  • 37 Van Veldhuizen JJ, Garber SB, Kingsbury JS, Hoveyda AH. J. Am. Chem. Soc. 2002; 124: 4954
  • 38 Chatterjee AK, Choi T.-L, Sanders DP, Grubbs RH. J. Am. Chem. Soc. 2003; 125: 11360
  • 39 Hong SH, Day MW, Grubbs RH. J. Am. Chem. Soc. 2004; 126: 7414
  • 40 Slugovc C, Perner B, Stelzer F, Mereiter K. Organometallics 2004; 23: 3622
  • 41 Romero PE, Piers WE, McDonald R. Angew. Chem. Int. Ed. 2004; 43: 6161
  • 42 Yang L, Mayr M, Wurst K, Buchmeiser MR. Chem.–Eur. J. 2004; 10: 5761
  • 43 Van Veldhuizen JJ, Campbell JE, Giudici RE, Hoveyda AH. J. Am. Chem. Soc. 2005; 127: 6877
  • 44 Galan BR, Gembicky M, Dominiak PM, Keister JB, Diver ST. J. Am. Chem. Soc. 2005; 127: 15702
  • 45 Vehlow K, Maechling S, Blechert S. Organometallics 2006; 25: 25
  • 46 Ritter T, Day MW, Grubbs RH. J. Am. Chem. Soc. 2006; 128: 11768
  • 47 Costabile C, Cavallo L. J. Am. Chem. Soc. 2004; 126: 9592
  • 48 Hillier AC, Sommer WJ, Yong BS, Petersen JL, Cavallo L, Nolan SP. Organometallics 2003; 22: 4322
  • 49 Gillingham DG, Hoveyda AH. Angew. Chem. Int. Ed. 2007; 46: 3860
  • 50 Hong SH, Grubbs RH. J. Am. Chem. Soc. 2006; 128: 3508
  • 51 Anderson DR, Lavallo V, OʼLeary DJ, Bertrand G, Grubbs RH. Angew. Chem. Int. Ed. 2007; 46: 7262
  • 52 Clavier H, Nolan SP. Chem.–Eur. J. 2007; 13: 8029
  • 53 Stewart IC, Ung T, Pletnev AA, Berlin JM, Grubbs RH, Schrodi Y. Org. Lett. 2007; 9: 1589
  • 54 Chung CK, Grubbs RH. Org. Lett. 2008; 10: 2693
  • 55 Wang D, Wurst K, Knolle W, Decker U, Prager L, Naumov S, Buchmeiser MR. Angew. Chem. Int. Ed. 2008; 47: 3267
  • 56 Vorfalt T, Leuthäußer S, Plenio H. Angew. Chem. Int. Ed. 2009; 48: 5191
  • 57 Piermattei A, Karthikeyan S, Sijbesma RP. Nat. Chem. 2009; 1: 133
  • 58 Samojłowicz C, Bieniek M, Grela K. Chem. Rev. 2009; 109: 3708
  • 59 Vougioukalakis GC, Grubbs RH. Chem. Rev. 2010; 110: 1746
  • 60 Ragone F, Poater A, Cavallo L. J. Am. Chem. Soc. 2010; 132: 4249
  • 61 Endo K, Grubbs RH. J. Am. Chem. Soc. 2011; 133: 8525
  • 62 Buchmeiser MR, Sen S, Unold J, Frey W. Angew. Chem. Int. Ed. 2014; 53: 9384