Cazin, C.  et al.: 2018 Science of Synthesis, 2016/5b: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2 DOI: 10.1055/sos-SD-224-00003
N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2

2.1.2 Ring-Closing 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

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

This chapter describes the use of ruthenium alkylidene complexes bearing N-heterocyclic carbene ligands as catalysts for the preparation of cyclic compounds (from 5- to 33-membered rings) by metathesis. Also included are examples of asymmetric metathesis using catalysts bearing chiral N-heterocyclic carbenes.

 
  • 1 Metathesis in Natural Product Synthesis. Cossy J, Arseniyadis S, Meyer C, EdS. Wiley-VCH; Weinheim, Germany 2010
  • 2 Nolan SP, Clavier H. Chem. Soc. Rev. 2010; 39: 3305
  • 3 Schmidt B, Hauke S, Krehl S, Kunz O, In Comprehensive Organic Synthesis, 2nd ed.,. Knochel P, Molander GA. Elsevier; Amsterdam 2014); Vol. . 5, p  1400.
  • 4 van Lierop BJ, Lummiss JAM, Fogg DE, In Olefin Metathesis: Theory and Practice. Grela K, Ed.;. Wiley Hoboken, NJ 2014); p ; 85
  • 5 Cossy J, In Olefin Metathesis: Theory and Practice. Grela K, Ed.;. Wiley Hoboken, NJ 2014); p ; 287
  • 6 Nguyen ST, Johnson LK, Grubbs RH, Ziller JW. J. Am. Chem. Soc. 1992; 114: 3974
  • 7 Nguyen ST, Grubbs RH, Ziller JW. J. Am. Chem. Soc. 1993; 115: 9858
  • 8 Schwab P, France MB, Ziller JW, Grubbs RH. Angew. Chem. Int. Ed. Engl. 1995; 34: 2039
  • 9 Schwab P, Grubbs RH, Ziller JW. J. Am. Chem. Soc. 1996; 118: 100
  • 10 Vougioukalakis GC, Grubbs RH. Chem. Rev. 2010; 110: 1746
  • 11 Weskamp T, Schattenmann WC, Spiegler M, Herrmann WA. Angew. Chem. Int. Ed. 1998; 37: 2490
  • 12 Vorfalt T, Leuthäußer S, Plenio H. Angew. Chem. Int. Ed. 2009; 48: 5191
  • 13 Sashuk V, Peeck LH, Plenio H. Chem.–Eur. J. 2010; 16: 3983
  • 14 Huang J, Stevens ED, Nolan SP, Petersen JL. J. Am. Chem. Soc. 1999; 121: 2674
  • 15 Scholl M, Trnka TM, Morgan JP, Grubbs RH. Tetrahedron Lett. 1999; 40: 2247
  • 16 Fürstner A, Thiel OR, Ackermann L, Schanz H.-J, Nolan SP. J. Org. Chem. 2000; 65: 2204
  • 17 Scholl M, Ding S, Lee CW, Grubbs RH. Org. Lett. 1999; 1: 953
  • 18 Occhipinti G, Bjørsvik H.-R, Jensen VR. J. Am. Chem. Soc. 2006; 128: 6952
  • 19 Fürstner A, Ackermann L, Gabor B, Goddard R, Lehmann CW, Mynott R, Stelzer F, Thiel OR. Chem.–Eur. J. 2001; 7: 3236
  • 20 Dinger MB, Mol JC. Adv. Synth. Catal. 2002; 344: 671
  • 21 Courchay FC, Sworen JC, Wagener KB. Macromolecules 2003; 36: 8231
  • 22 Vieille-Petit L, Luan X, Gatti M, Blumentritt S, Linden A, Clavier H, Nolan SP, Dorta R. Chem. Commun. (Cambridge) 2009; 3783
  • 23 Vieille-Petit L, Clavier H, Linden A, Blumentritt S, Nolan SP, Dorta R. Organometallics 2010; 29: 775
  • 24 Stewart IC, Ung T, Pletnev AA, Berlin JM, Grubbs RH, Schrodi Y. Org. Lett. 2007; 9: 1589
  • 25 Boeda F, Clavier H, Nolan SP. Chem. Commun. (Cambridge) 2008; 2726
  • 26 Fürstner A, Liebl M, Hill AF, Wilton-Ely JDET. Chem. Commun. (Cambridge) 1999; 601
  • 27 Fürstner A, Guth O, Düffels A, Seidel G, Liebl M, Gabor B, Mynott R. Chem.–Eur. J. 2001; 7: 4811
  • 28 Jafarpour L, Schanz H.-J, Stevens ED, Nolan SP. Organometallics 1999; 18: 5416
  • 29 Clavier H, Nolan SP. Chem.–Eur. J. 2007; 13: 8029
  • 30 Clavier H, Urbina-Blanco CA, Nolan SP. Organometallics 2009; 28: 2848
  • 31 Manzini S, Urbina-Blanco CA, Slawin AMZ, Nolan SP. Organometallics 2012; 31: 6514
  • 32 Bantreil X, Schmid TE, Randall RAM, Slawin AMZ, Cazin CSJ. Chem. Commun. (Cambridge) 2010; 46: 7115
  • 33 Harrity JPA, Visser MS, Gleason JD, Hoveyda AH. J. Am. Chem. Soc. 1997; 119: 1488
  • 34 Kingsbury JS, Harrity JPA, Bonitatebus Jr. PJ, Hoveyda AH. J. Am. Chem. Soc. 1999; 121: 791
  • 35 Garber SB, Kingsbury JS, Gray BL, Hoveyda AH. J. Am. Chem. Soc. 2000; 122: 8168
  • 36 Gessler S, Randl S, Blechert S. Tetrahedron Lett. 2000; 41: 9973
  • 37 Clavier H, Grela K, Kirschning A, Mauduit M, Nolan SP. Angew. Chem. Int. Ed. 2007; 46: 6786
  • 38 Wakamatsu H, Blechert S. Angew. Chem. Int. Ed. 2002; 41: 794
  • 39 Grela K, Harutyunyan S, Michrowska A. Angew. Chem. Int. Ed. 2002; 41: 4038
  • 40 Zhan Z.-Y. WO 2007 003 135, 2007
  • 41 Rix D, Caijo F, Laurent I, Boeda F, Clavier H, Nolan SP, Mauduit M. J. Org. Chem. 2008; 73: 4225
  • 42 Bieniek M, Michrowska A, Usanov DL, Grela K. Chem.–Eur. J. 2008; 14: 806
  • 43 Edwards GA, Culp PA, Chalker JM. Chem. Commun. (Cambridge) 2015; 51: 515
  • 44 Lin YA, Chalker JM, Floyd N, Bernardes GJL, Davis BG. J. Am. Chem. Soc. 2008; 130: 9642
  • 45 Hoye TR, Jeffrey CS, Tennakoon MA, Wang J, Zhao H. J. Am. Chem. Soc. 2004; 126: 10210
  • 46 Wallace DJ. Angew. Chem. Int. Ed. 2005; 44: 1912
  • 47 Guidone S, Songis O, Nahra F, Cazin CSJ. ACS Catal. 2015; 5: 2697
  • 48 Maier ME. Angew. Chem. Int. Ed. 2000; 39: 2073
  • 49 Michaut A, Rodriguez J. Angew. Chem. Int. Ed. 2006; 45: 5740
  • 50 Bourgeois D, Pancrazi A, Nolan SP, Prunet J. J. Organomet. Chem. 2002; 643–644: 247
  • 51 Paquette LA, Efremov I. J. Am. Chem. Soc. 2001; 123: 4492
  • 52 Fürstner A, Radkowski K, Wirtz C, Goddard R, Lehmann CW, Mynott R. J. Am. Chem. Soc. 2002; 124: 7061
  • 53 Fürstner A, Schlede M. Adv. Synth. Catal. 2002; 344: 657
  • 54 De Bo G, Markó IE. Eur. J. Org. Chem. 2011; 1859
  • 55 Sundararaju B, Sridhar T, Achard M, Sharma GVM, Bruneau C. Eur. J. Org. Chem. 2010; 6092
  • 56 Sundararaju B, Sridhar T, Achard M, Sharma GVM, Bruneau C. Eur. J. Org. Chem. 2013; 6433
  • 57 Cusson J.-P, Chénard E, Hanessian S. Synthesis 2015; 1317
  • 58 Brown MK, Hoveyda AH. J. Am. Chem. Soc. 2008; 130: 12904
  • 59 Prunet J. Angew. Chem. Int. Ed. 2003; 42: 2826
  • 60 Gradillas A, Pérez-Castells J. Angew. Chem. Int. Ed. 2006; 45: 6086
  • 61 Lee CW, Grubbs RH. Org. Lett. 2000; 2: 2145
  • 62 Grisi F, Costabile C, Grimaldi A, Viscardi C, Saturnino C, Longo P. Eur. J. Org. Chem. 2012; 5928
  • 63 Lee CW, Grubbs RH. J. Org. Chem. 2001; 66: 7155
  • 64 Fürstner A, Dierkes T, Thiel OR, Blanda G. Chem.–Eur. J. 2001; 7: 5286
  • 65 Wagner J, Martin Cabrejas LM, Grossmith CE, Papageorgiou C, Senia F, Wagner D, France J, Nolan SP. J. Org. Chem. 2000; 65: 9255
  • 66 Tannert R, Milroy L.-G, Ellinger B, Hu T.-S, Arndt H.-D, Waldmann H. J. Am. Chem. Soc. 2010; 132: 3063
  • 67 Arndt H.-D, Rizzo S, Nöcker C, Wakchaure VN, Milroy L.-G, Bieker V, Calderon A, Tran TTN, Brand S, Dehmelt L, Waldmann H. Chem.–Eur. J. 2015; 21: 5311
  • 68 Ghosh S, Ghosh S, Sarkar N. J. Chem. Sci. (Berlin, Ger.) 2006; 118: 223
  • 69 Díaz-Oltra S, Angulo-Pachón CA, Murga J, Carda M, Marco JA. J. Org. Chem. 2010; 75: 1775
  • 70 Fürstner A, Thiel OR, Blanda G. Org. Lett. 2000; 2: 3731
  • 71 Wang Y, Jimenez M, Hansen AS, Raiber E.-A, Schreiber SL, Young DW. J. Am. Chem. Soc. 2011; 133: 9196
  • 72 Gallenkamp D, Fürstner A. J. Am. Chem. Soc. 2011; 133: 9232
  • 73 Marx VM, Herbert MB, Keitz BK, Grubbs RH. J. Am. Chem. Soc. 2013; 135: 94
  • 74 Rosebrugh LE, Herbert MB, Marx VM, Keitz BK, Grubbs RH. J. Am. Chem. Soc. 2013; 135: 1276
  • 75 Endo K, Herbert MB, Grubbs RH. Organometallics 2013; 32: 5128
  • 76 Diaba F, Pujol-Grau C, Martínez-Laporta A, Fernández I, Bonjoch J. Org. Lett. 2015; 17: 568
  • 77 Ablialimov O, Kędziorek M, Malińska M, Woźniak K, Grela K. Organometallics 2014; 33: 2160
  • 78 Nicola T, Brenner M, Donsbach K, Kreye P. Org. Process Res. Dev. 2005; 9: 513
  • 79 Farina V, Shu C, Zeng X, Wei X, Han Z, Yee NK, Senanayake CH. Org. Process Res. Dev. 2009; 13: 250
  • 80 Kong J, Chen C, Balsells-Padros J, Cao Y, Dunn RF, Dolman SJ, Janey J, Li H, Zacuto MJ. J. Org. Chem. 2012; 77: 3820
  • 81 Guduru SKR, Jimmidi R, Deora GS, Arya P. Org. Lett. 2015; 17: 480
  • 82 Trost BM, Yang H, Thiel OR, Frontier AJ, Brindle CS. J. Am. Chem. Soc. 2007; 129: 2206
  • 83 Pérez-Balado C, Nebbioso A, Rodríguez-Graña P, Minichiello A, Miceli M, Altucci L, de Lera ÁR. J. Med. Chem. 2007; 50: 2497
  • 84 Hoveyda AH, Malcolmson SJ, Meek SJ, Zhugralin AR. Angew. Chem. Int. Ed. 2010; 49: 34
  • 85 Kress S, Blechert S. Chem. Soc. Rev. 2012; 41: 4389
  • 86 Hoveyda AH. J. Org. Chem. 2014; 79: 4763
  • 87 Fujimura O, Grubbs RH. J. Am. Chem. Soc. 1996; 118: 2499
  • 88 Alexander JB, La DS, Cefalo DR, Hoveyda AH, Schrock RR. J. Am. Chem. Soc. 1998; 120: 4041
  • 89 La DS, Alexander JB, Cefalo DR, Graf DD, Hoveyda AH, Schrock RR. J. Am. Chem. Soc. 1998; 120: 9720
  • 90 Dolman SJ, Sattely ES, Hoveyda AH, Schrock RR. J. Am. Chem. Soc. 2002; 124: 6991
  • 91 Kiely AF, Jernelius JA, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2002; 124: 2868
  • 92 Tsang WCP, Hultzsch KC, Alexander JB, Bonitatebus Jr. PJ, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2003; 125: 2652
  • 93 Sattely ES, Cortez GA, Moebius DC, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2005; 127: 8526
  • 94 Lee A.-L, Malcolmson SJ, Puglisi A, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2006; 128: 5153
  • 95 Malcolmson SJ, Meek SJ, Sattely ES, Schrock RR, Hoveyda AH. Nature (London) 2008; 456: 933
  • 96 Harvey JS, Malcolmson SJ, Dunne KS, Meek SJ, Thompson AL, Schrock RR, Hoveyda AH, Gouverneur V. Angew. Chem. Int. Ed. 2009; 48: 762
  • 97 Ogasawara M, Watanabe S, Nakajima K, Takahashi T. J. Am. Chem. Soc. 2010; 132: 2136
  • 98 Ivry E, Ben-Asuly A, Goldberg I, Lemcoff NG. Chem. Commun. (Cambridge) 2015; 51: 3870
  • 99 Seiders TJ, Ward DW, Grubbs RH. Org. Lett. 2001; 3: 3225
  • 100 Funk TW, Berlin JM, Grubbs RH. J. Am. Chem. Soc. 2006; 128: 1840
  • 101 Grisi F, Costabile C, Gallo E, Mariconda A, Tedesco C, Longo P. Organometallics 2008; 27: 4649
  • 102 Fournier P.-A, Collins SK. Organometallics 2007; 26: 2945
  • 103 Fournier P.-A, Savoie J, Stenne B, Bédard M, Grandbois A, Collins SK. Chem.–Eur. J. 2008; 14: 8690
  • 104 Tiede S, Berger A, Schlesiger D, Rost D, Lühl A, Blechert S. Angew. Chem. Int. Ed. 2010; 49: 3972
  • 105 Savoie J, Stenne B, Collins SK. Adv. Synth. Catal. 2009; 351: 1826
  • 106 Stenne B, Timperio J, Savoie J, Dudding T, Collins SK. Org. Lett. 2010; 12: 2032
  • 107 Paradiso V, Bertolasi V, Grisi F. Organometallics 2014; 33: 5932
  • 108 Kannenberg A, Rost D, Eibauer S, Tiede S, Blechert S. Angew. Chem. Int. Ed. 2011; 50: 3299
  • 109 Gawin R, Pieczykolan M, Malińska M, Woźniak K, Grela K. Synlett 2013; 24: 1250
  • 110 Van Veldhuizen JJ, Garber SB, Kingsbury JS, Hoveyda AH. J. Am. Chem. Soc. 2002; 124: 4954
  • 111 Van Veldhuizen JJ, Gillingham DG, Garber SB, Kataoka O, Hoveyda AH. J. Am. Chem. Soc. 2003; 125: 12502
  • 112 Van Veldhuizen JJ, Campbell JE, Giudici RE, Hoveyda AH. J. Am. Chem. Soc. 2005; 127: 6877
  • 113 Giudici RE, Hoveyda AH. J. Am. Chem. Soc. 2007; 129: 3824
  • 114 Endo K, Grubbs RH. J. Am. Chem. Soc. 2011; 133: 8525
  • 115 Keitz BK, Endo K, Herbert MB, Grubbs RH. J. Am. Chem. Soc. 2011; 133: 9686
  • 116 Hartung J, Dornan PK, Grubbs RH. J. Am. Chem. Soc. 2014; 136: 13029
  • 117 Grandbois A, Collins SK. Chem.–Eur. J. 2008; 14: 9323