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-224-00050
N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2

2.2 Polymerization, Oligomerization, and Telomerization Involving N-Heterocyclic Carbenes as Ligands or Initiators

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 an overview of recent developments in polymerization and oligomerization of alkenes and cyclic esters involving N-heterocyclic carbenes, both as ligands in organometallic catalysts and as organocatalysts. Telomerization reactions catalyzed by N-heterocyclic carbene–palladium complexes are also briefly discussed.

Key words

polymerization - oligomerization - telomerization - organocatalysis - ethene - styrene - norbornene - conjugated dienes - cyclic esters - N-heterocyclic carbenes
 
  • 1 Hopkinson MN, Richter C, Schedler M, Glorius F. Nature (London) 2014; 510: 485
  • 2 Zhang D, Zi G. Chem. Soc. Rev. 2015; 44: 1898
  • 3 Fèvre M, Pinaud J, Gnanou Y, Vignolle J, Taton D. Chem. Soc. Rev. 2013; 42: 2142
  • 4 Díez-González S, Marion N, Nolan SP. Chem. Rev. 2009; 109: 3612
  • 5 Naumann S, Dove AP. Polym. Chem. 2015; 6: 3185
  • 6 Resconi L, Chadwick JC, Cavallo L, In Comprehensive Organometallic Chemistry III. Crabtree RH, Mingos DMP, Eds.;. Elsevier; Oxford 2007);. Vol.  4, pp 1005.
    Google Scholar
  • 7 Makio H, Terao H, Iwashita A, Fujita T. Chem. Rev. 2011; 111: 2363
  • 8 Zhang D, Liu N. Organometallics 2009; 28: 499
  • 9 Bocchino C, Napoli M, Costabile C, Longo P. J. Polym. Sci., Part A: Polym. Chem. 2011; 49: 862
  • 10 Costabile C, Bocchino C, Napoli M, Longo P. J. Polym. Sci., Part A: Polym. Chem. 2012; 50: 3728
  • 11 Al-Batta A, Waltman AW, Grubbs RH. J. Organomet. Chem. 2011; 696: 2477
  • 12 Miyake GM, Akhtar MN, Fazal A, Jaseer EA, Daeffler CS, Grubbs RH. J. Organomet. Chem. 2013; 728: 1
  • 13 Kawai K, Fujita T. Top. Organomet. Chem. 2009; 26: 3
  • 14 Makio H, Kashiwa N, Fujita T. Adv. Synth. Catal. 2002; 344: 477
  • 15 Larocque TG, Badaj AC, Dastgir S, Lavoie GG. Dalton Trans. 2011; 40: 12705
  • 16 Abernethy CD, Cowley AH, Jones RA. J. Organomet. Chem. 2000; 596: 3
  • 17 Kelly III RA, Scott NM, Díez-González S, Stevens ED, Nolan SP. Organometallics 2005; 24: 3442
  • 18 Buchowicz W, Kozioł A, Jerzykiewicz LB, Lis T, Pasynkiewicz S, Pęcherzewska A, Pietrzykowski A. J. Mol. Catal. A: Chem. 2006; 257: 118
  • 19 Buchowicz W, Banach , Conder J, Guńka PA, Kubicki D, Buchalski P. Dalton Trans. 2014; 43: 5847
  • 20 Okada S, Park S, Matyjaszewski K. ACS Macro Lett. 2014; 3: 944
  • 21 Jung IG, Seo J, Chung YK, Shin MD, Chun S, Son SU. J. Polym. Sci., Part A: Polym. Chem. 2007; 45: 3042
  • 22 Kong Y, Ren H, Xu S, Song H, Liu B, Wang B. Organometallics 2009; 28: 5934
  • 23 Kong Y, Wen L, Song H, Xu S, Yang M, Liu B, Wang B. Organometallics 2011; 30: 153
  • 24 Dang L, Song H, Wang B. Organometallics 2014; 33: 6812
  • 25 Mainwald S, Weissenborn H, Sommer C, Müller G, Taube R. J. Organomet. Chem. 2001; 640: 1
  • 26 Barbier-Baudry D, Bonnet F, Domenichini B, Dormond M, Visseaux M. J. Organomet. Chem. 2002; 647: 167
  • 27 Wolpers J, Fuchs HB, Herrmann C, Hellermann W, Nordsiek K.-H. US 5 104 941, 1992
  • 28 Massie II JD, Hsu W.-L, Halasa AF, Sandstrom PH. US 5 356 997, 1994
  • 29 Wang B, Cui D, Lv K. Macromolecules 2008; 41: 1983
  • 30 Yao C, Liu D, Li P, Wu C, Li S, Liu B, Cui D. Organometallics 2014; 33: 684
  • 31 Yao C, Lin F, Wang M, Liu D, Liu B, Liu N, Wang Z, Long S, Wu C, Cui D. Macromolecules 2015; 48: 1999
  • 32 Dechy-Cabaret O, Martin-Vaca B, Bourissou D. Chem. Rev. 2004; 104: 6147
  • 33 Sauer A, Kapelski A, Fliedel C, Dagorne S, Kol M, Okuda J. Dalton Trans. 2013; 42: 9007
  • 34 Romain C, Heinrich B, Bellemin-Laponnaz S, Dagorne S. Chem. Commun. (Cambridge) 2012; 48: 2213
  • 35 Romain C, Brelot L, Bellemin-Laponnaz S, Dagorne S. Organometallics 2010; 29: 1191
  • 36 Zhao N, Hou G, Deng X, Zi G, Walter MD. Dalton Trans. 2014; 43: 8261
  • 37 Romain C, Fliedel C, Bellemin-Laponnaz S, Dagorne S. Organometallics 2014; 33: 5730
  • 38 Schnee G, Fliedel C, Avilés T, Dagorne S. Eur. J. Inorg. Chem. 2013; 3699
  • 39 Fliedel C, Vila-Viçosa D, Calhorda MJ, Dagorne S, Avilés T. ChemCatChem 2014; 6: 1357
  • 40 Zheng X, Zhang C, Wang Z. J. Organomet. Chem. 2015; 783: 105
  • 41 Zhang M, Ni X, Shen Z. Organometallics 2014; 33: 6861
  • 42 Connor EF, Nyce GW, Myers M, Möck A, Hedrick JL. J. Am. Chem. Soc. 2002; 124: 914
  • 43 Nyce GW, Glauser T, Connor EF, Möck A, Waymouth RM, Hedrick JL. J. Am. Chem. Soc. 2003; 125: 3046
  • 44 Csihony S, Culkin DA, Sentman AC, Dove AP, Waymouth RM, Hedrick JL. J. Am. Chem. Soc. 2005; 127: 9079
  • 45 Dove AP, Li H, Pratt RC, Lohmeijer BGG, Culkin DA, Waymouth RM, Hedrick JL. Chem. Commun. (Cambridge) 2006; 2881
  • 46 Naumann S, Schmidt FG, Frey W, Buchmeiser MR. Polym. Chem. 2013; 4: 4172
  • 47 Brown HA, Waymouth RM. Acc. Chem. Res. 2013; 46: 2585
  • 48 Jeong W, Hedrick JL, Waymouth RM. J. Am. Chem. Soc. 2007; 129: 8414
  • 49 Shin EJ, Jeong W, Brown HA, Koo BJ, Hedrick JL, Waymouth RM. Macromolecules 2011; 44: 2773
  • 50 Brown HA, Xiong S, Medvedev AG, Chang YA, Abu-Omar MM, Caruthers JM, Waymouth RM. Macromolecules 2014; 47: 2955
  • 51 Shin EJ, Brown HA, Gonzalez S, Jeong W, Hedrick JL, Waymouth RM. Angew. Chem. Int. Ed. 2011; 50: 6388
  • 52 McGuinness DS. Dalton Trans. 2009; 6915
  • 53 McGuinness DS, Gibson VC, Wass DF, Steed JW. J. Am. Chem. Soc. 2003; 125: 12716
  • 54 McGuinness DS, Gibson VC, Steed JW. Organometallics 2004; 23: 6288
  • 55 Hameury S, de Frémont P, Breuil PR, Olivier-Bourbigou H, Braunstein P. Inorg. Chem. 2014; 53: 5189
  • 56 Dagorne S, Bellemin-Laponnaz S, Romain C. Organometallics 2013; 32: 2736
  • 57 Cámpora J, de la Tabla LO, Palma P, Álvarez E, Lahoz FJ, Mereiter K. Organometallics 2006; 25: 3314
  • 58 Nielsen DJ, Cavell KJ, In N-Heterocyclic Carbenes in Synthesis Nolan SP, Ed.;. Wiley-VCH Weinheim, Germany 2006);; p 73
  • 59 Torrente-Murciano L, Lapkin A, Nielsen DJ, Fallis I, Cavell KJ. Green Chem. 2010; 12: 866
  • 60 Jackstell R, Harkal S, Jiao H, Spannenberg A, Borgmann C, Röttger D, Nierlich F, Elliot M, Niven S, Cavell K, Navarro O, Viciu MS, Nolan SP, Beller M. Chem.–Eur. J. 2004; 10: 3891
  • 61 Mesnager J, Lammel P, Jeanneau E, Pinel C. Appl. Catal., A 2009; 368: 22
  • 62 Grotevendt A, Bartolome M, Spannenberg A, Nielsen DJ, Jackstell R, Cavell KJ, Oro LA, Beller M. Tetrahedron Lett. 2007; 48: 9203