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Cazin, C.  et al.: 2018 Science of Synthesis, 2016/5b: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2 DOI: 10.1055/sos-SD-224-00184
N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2

2.7.2 Covalently Immobilized N-Heterocyclic Carbene Complexes

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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

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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

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Abstract

This chapter focuses on the preparation and the catalytic performance of metal–NHC complexes immobilized on oxide supports, which are designed so that the metal–NHC complex is maintained on the support during catalysis. The major scientific contributions for the covalent immobilization of metal–NHC complexes onto various oxides are covered, with an emphasis on the most distinguished examples. Particular attention is directed toward the anchoring of metal complexes via the substituents or the backbone of the NHC ligand, or via another X/L-type ligand that is not expected to suffer from decoordination during the catalytic process.

Key words

N-heterocyclic carbene complexes - supported catalysts - grafting - immobilization - oxides - sol-gel process - catalysis
 
  • 1 Synthesis of Solid Catalysts. de Jong KP, Ed.;. Wiley-VCH; Weinheim, Germany 2009
    Google Scholar
  • 2 Ranganath KVS, Onitsuka S, Kumar AK, Inanaga J. Catal. Sci. Technol. 2013; 3: 2161
  • 3 Sommer WJ, Weck M. Coord. Chem. Rev. 2007; 25: 860
  • 4 Cazin CSJ. C. R. Chim. 2009; 12: 1173
  • 5 Monge-Marcet A, Pleixats R, Cattoën X, Wong Chi Man M. Catal. Sci. Technol. 2011; 1: 1544
  • 6 Buchmeiser MR. Chem. Rev. 2009; 109: 303
  • 7 Bergbreiter DE, Tian J, Hongfa C. Chem. Rev. 2009; 109: 530
  • 8 Park JH, Raza F, Jeon S.-J, Kim H.-I, Kang TW, Yim D, Kim J.-H. Tetrahedron Lett. 2014; 55: 3426
  • 9 Shang N, Gao S, Feng C, Zhang H, Wang C, Wang Z. RSC Adv. 2013; 3: 21863
  • 10 Movahed SK, Esmatpoursalmani R, Bazgir A. RSC Adv. 2014; 4: 14586
  • 11 Ranganath KVS, Kloesges J, Schäfer AH, Glorius F. Angew. Chem. Int. Ed. 2010; 49: 7786
  • 12 Wittmann S, Majoral J.-P, Grass RN, Stark WJ, Reiser O. Green Process. Synth. 2012; 1: 275
  • 13 Maishal TK, Alauzun J, Basset J.-M, Copéret C, Corriu RJP, Jeanneau E, Mehdi A, Reyé C, Veyre L, Thieuleux C. Angew. Chem. Int. Ed. 2008; 47: 8654
  • 14 Conley MP, Copéret C, Thieuleux C. ACS Catal. 2014; 4: 1458
  • 15 Lelli M, Gajan D, Lesage A, Caporini MA, Vitzthum V, Miéville P, Héroguel F, Rascón F, Roussey A, Thieuleux C, Boualleg M, Veyre L, Bodenhausen G, Copéret C, Emsley L. J. Am. Chem. Soc. 2011; 133: 2104
  • 16 Dastgir S, Coleman KS, Green MLH. Dalton Trans. 2011; 40: 661
  • 17 Martínez A, Krinsky JL, Peñafiel I, Castillón S, Loponov K, Lapkin A, Godard C, Claver C. Catal. Sci. Technol. 2015; 5: 310
  • 18 Ghiaci M, Zarghani M, Khojastehnezhad A, Moeinpour F. RSC Adv. 2014; 4: 15496
  • 19 Yang H, Han X, Li G, Wang Y. Green Chem. 2009; 11: 1184
  • 20 Weck M, Jones CW. Inorg. Chem. 2007; 46: 1865
  • 21 Alam MN, Sarkar SM. React. Kinet., Mech. Catal. 2011; 103: 493
  • 22 Wan L, Yu H, Cai C. J. Fluorine Chem. 2012; 140: 107
  • 23 Lee S.-M, Yoon H.-J, Kim J.-H, Chung W.-J, Lee Y.-S. Pure Appl. Chem. 2007; 79: 1553
  • 24 Tandukar S, Sen A. J. Mol. Catal. A: Chem. 2007; 268: 112
  • 25 Qiu H, Sarkar SM, Lee D.-H, Jin M.-J. Green Chem. 2008; 10: 37
  • 26 Karimi B, Enders D. Org. Lett. 2006; 8: 1237
  • 27 Aksin , Türkmen H, Artok L, Çetinkaya B, Ni C, Büyükgüngör O, Özkal E. J. Organomet. Chem. 2006; 691: 3027
  • 28 Tyrrell E, Whiteman L, Williams N. J. Organomet. Chem. 2011; 696: 3465
  • 29 Villaverde G, Corma A, Iglesias M, Sánchez F. ChemCatChem 2011; 3: 1320
  • 30 Kume Y, Qiao K, Tomida D, Yokoyama C. Catal. Commun. 2008; 9: 369
  • 31 Hou Y, Ji X, Liu G, Tang J, Zheng J, Liu Y, Zhang W, Jia M. Catal. Commun. 2009; 10: 1459
  • 32 Johnson BFG, Raynor SA, Shephard DS, Mashmeyer T, Thomas JM, Sankar G, Bromley S, Oldroyd R, Gladden L, Mantle MD. Chem. Commun. (Cambridge) 1999; 1167
  • 33 Rohlfing Y, Wöhrle D, Wark M, Schulz-Ekloff G, Rathousky J, Zukal A. Stud. Surf. Sci. Catal. 2000; 129: 295
  • 34 Krinsky JL, Martínez A, Godard C, Castillón S, Claver C. Adv. Synth. Catal. 2014; 356: 460
  • 35 Li P, Kawi S. J. Catal. 2008; 257: 23
  • 36 Yang H, Li J, Yang J, Liu Z, Yang Q, Li C. Chem. Commun. (Cambridge) 2007; 1086
  • 37 del Pozo C, Corma A, Iglesias M, Sánchez F. Organometallics 2010; 29: 4491
  • 38 Villaverde G, Corma A, Iglesias M, Sánchez F. ACS Catal. 2012; 2: 399
  • 39 Li P, Herrmann WA, Kühn FE. ChemCatChem 2013; 5: 3324
  • 40 Frey GD, Rentzsch CF, von Preysing D, Scherg T, Mühlhofer M, Herdtweck E, Herrmann WA. J. Organomet. Chem. 2006; 691: 5725
  • 41 Lázaro G, Fernández-Alvarez FJ, Iglesias M, Horna C, Vispe E, Sancho R, Lahoz FJ, Iglesias M, Pérez-Torrente JJ, Oro LA. Catal. Sci. Technol. 2014; 4: 62
  • 42 Corma A, Gutiérrez-Puebla E, Iglesias M, Monge A, Pérez-Ferreras S, Sánchez F. Adv. Synth. Catal. 2006; 348: 1899
  • 43 del Pozo C, Corma A, Iglesias M, Sánchez F. J. Catal. 2012; 291: 110
  • 44 del Pozo C, Corma A, Iglesias M, Sánchez F. Green Chem. 2011; 13: 2471
  • 45 Çetinkaya B, Gürbüz N, Seçkin T, Özdemir I. J. Mol. Catal. A: Chem. 2002; 184: 31
  • 46 Monge-Marcet A, Pleixats R, Cattoën X, Wong Chi Man M. Tetrahedron 2013; 69: 341
  • 47 Monge-Marcet A, Pleixats R, Cattoën X, Wong Chi Man M. J. Sol-Gel Sci. Technol. 2013; 65: 93
  • 48 Marciniec B, Rogalski S, Potrzebowski MJ, Pietraszuk C. ChemCatChem 2011; 3: 904
  • 49 Li L, Shi J. Adv. Synth. Catal. 2005; 347: 1745
  • 50 Lim J, Lee SS, Ying JY. Chem. Commun. (Cambridge) 2008; 4312
  • 51 Prühs S, Lehmann CW, Fürstner A. Organometallics 2004; 23: 280
  • 52 Park KH, Kim S, Chung YK. Bull. Korean Chem. Soc. 2008; 29: 2057
  • 53 Bek D, Žilková N, Dědeček J, Sedláček J, Balcar H. Top. Catal. 2010; 53: 200
  • 54 Jee J.-E, Cheong JL, Lim J, Chen C, Hong SH, Lee SS. J. Org. Chem. 2013; 78: 3048
  • 55 Dragutan I, Dragutan V, Delaude L, Demonceau A. ARKIVOC 2005),; x, 206
  • 56 Allen DP, Van Wingerden MM, Grubbs RH. Org. Lett. 2009; 11: 1261
  • 57 Karamé I, Boualleg M, Camus J.-M, Maishal TK, Alauzun J, Basset J.-M, Copéret C, Corriu RJP, Jeanneau E, Mehdi A, Reyé C, Veyre L, Thieuleux C. Chem.–Eur. J. 2009; 15: 11820
  • 58 Wang D, Guo X.-Q, Wang C.-X, Wang Y.-N, Zhong R, Zhu X.-H, Cai L.-H, Gao Z.-W, Hou X.-F. Adv. Synth. Catal. 2013; 355: 1117
  • 59 Yoon H.-J, Choi J.-W, Kang H, Kang T, Lee S.-M, Jun B.-H, Lee Y.-S. Synlett 2010; 2518
  • 60 Wang M, Li P, Wang L. Eur. J. Org. Chem. 2008; 2255
  • 61 Wan L, Cai C. Catal. Lett. 2012; 142: 1134
  • 62 Yang Y, Rioux RM. Green Chem. 2014; 16: 3916
  • 63 Corriu RJP. Eur. J. Inorg. Chem. 2001; 1109
  • 64 Mehdi A, Reyé C, Corriu R. Chem. Soc. Rev. 2011; 40: 563
  • 65 Hoffmann F, Cornelius M, Morell J, Fröba M. Angew. Chem. Int. Ed. 2006; 45: 3216
  • 66 Gajan D, Schwarzwälder M, Conley MP, Grüning WR, Rossini AJ, Zagdoun A, Lelli M, Yulikov M, Jeschke G, Sauvée C, Ouari O, Tordo P, Veyre L, Lesage A, Thieuleux C, Emsley L, Copéret C. J. Am. Chem. Soc. 2013; 135: 15459
  • 67 Samantaray MK, Alauzun J, Gajan D, Kavitake S, Mehdi A, Veyre L, Lelli M, Lesage A, Emsley L, Copéret C, Thieuleux C. J. Am. Chem. Soc. 2013; 135: 3193
  • 68 Romanenko I, Gajan D, Sayah R, Crozet D, Jeanneau E, Lucas C, Leroux L, Veyre L, Lesage A, Emsley L, Lacôte E, Thieuleux C. Angew. Chem. Int. Ed. 2015; 54: 12937
  • 69 Nguyen TP, Hesemann P, Gaveau P, Moreau JJE. J. Mater. Chem. 2009; 19: 9286
  • 70 Polshettiwar V, Hesemann P, Moreau JJE. Tetrahedron Lett. 2007; 48: 5363
  • 71 Trilla M, Pleixats R, Wong Chi Man M, Bied C, Moreau JJE. Adv. Synth. Catal. 2008; 350: 577
  • 72 Trilla M, Borja G, Pleixats R, Wong Chi Man M, Bied C, Moreau JJE. Adv. Synth. Catal. 2008; 350: 2566
  • 73 Yang H, Han X, Li G, Ma Z, Hao Y. J. Phys. Chem. C 2010; 114: 22221
  • 74 Liu G, Hou M, Wu T, Jiang T, Fan H, Yang G, Han B. Phys. Chem. Chem. Phys. 2011; 13: 2062
  • 75 Borja G, Monge-Marcet A, Pleixats R, Parella T, Cattoën X, Wong Chi Man M. Eur. J. Org. Chem. 2012; 3625
  • 76 Marion N, de Frémont P, Puijk IM, Ecarnot EC, Amoroso D, Bell A, Nolan SP. Adv. Synth. Catal. 2007; 349: 2380
  • 77 OʼBrien CJ, Kantchev EAB, Valente C, Hadei N, Chass GA, Lough A, Hopkinson AC, Organ MG. Chem.–Eur. J. 2006; 12: 4743
  • 78 Conley MP, Drost RM, Baffert M, Gajan D, Elsevier C, Franks WT, Oschkinat H, Veyre L, Zagdoun A, Rossini A, Lelli M, Lesage A, Casano G, Ouari O, Tordo P, Emsley L, Copéret C, Thieuleux C. Chem.–Eur. J. 2013; 19: 12234
  • 79 Monge-Marcet A, Pleixats R, Cattoën X, Wong Chi Man M. J. Mol. Catal. A: Chem. 2012; 357: 59
  • 80 Baffert M, Maishal TK, Mathey L, Copéret C, Thieuleux C. ChemSusChem 2011; 4: 1762
  • 81 Kavitake S, Samantaray MK, Dehn R, Deuerlein S, Limbach M, Schachner JA, Jeanneau E, Copéret C, Thieuleux C. Dalton Trans. 2011; 40: 12443
  • 82 Maishal TK, Boualleg M, Bouhrara M, Copéret C, Jeanneau E, Veyre L, Thieuleux C. Eur. J. Inorg. Chem. 2010; 5005