Versatile Methods for the Synthesis of Si(OR)3-Functionalised Imidazolium Salts, Potential Precursors for Heterogeneous NHC Catalysts and Composite Materials

Catherine S. J. Cazin; Michael Veith; Pierre Braunstein; Robin B. Bedford

doi:10.1055/s-2005-861784

PAPER

Versatile Methods for the Synthesis of Si(OR)₃-Functionalised Imidazolium Salts, Potential Precursors for Heterogeneous NHC Catalysts and Composite Materials

Catherine S. J. Cazin^a,b, Michael Veith*^a, Pierre Braunstein*^c, Robin B. Bedford*^b
^a Universität des Saarlandes, Anorganische Chemie, Geb. 23.1, Postfach 151150, 66041 Saarbrücken, Germany
Fax: +49(681)3023995; e-Mail: veith@mx.uni-saarland.de;
^b Department of Chemistry, University of Exeter, Exeter EX4 4QD, UK
^c Laboratoire de Chimie de Coordination, UMR 7513 CNRS, Université Louis Pasteur, 4 rue Blaise Pascal, 67070 Strasbourg, France

Abstract

Alle Artikel dieser Rubrik

Abstract

Versatile methodologies for the synthesis of N-alkyl and N-aryl, and alkoxysilyl-functionalised mono- and bis-imidazolium salts are discussed. Such salts could find applications for heterogeneous N-heterocyclic catalysts and sol-gel materials.

Key words

ionic liquids - carbenes - supported catalysis - imidazolium salts - alkoxysilyl

Volltext

Referenzen

References

For recent reviews on ionic liquids, see:

<A NAME="RZ17204SS-1A">1a</A> Holbrey JD. Seddon KR. Clean Prod. Process 1999, 1: 223

<A NAME="RZ17204SS-1B">1b</A> Welton T. Chem. Rev. 1999, 99: 2071

<A NAME="RZ17204SS-1C">1c</A> Wasserscheid P. Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772

<A NAME="RZ17204SS-1D">1d</A> Gordon CM. Appl. Catal., A 2001, 222: 101

<A NAME="RZ17204SS-1E">1e</A> Sheldon R. Chem. Commun. 2001, 2399

<A NAME="RZ17204SS-1F">1f</A> Zhao D. Wu M. Kou Y. Min E. Catal. Today 2002, 74: 157

<A NAME="RZ17204SS-1G">1g</A> Tzschucke CC. Markert C. Bannwarth W. Roller S. Hebel A. Haag R. Angew. Chem. Int. Ed. 2002, 41: 3964

<A NAME="RZ17204SS-1H">1h</A> Olivier-Bourbigou H. Magna L. J. Mol. Catal. A: Chem. 2002, 182-183: 419

<A NAME="RZ17204SS-1I">1i</A> Dupont J. de Souza RF. Suarez PAZ. Chem. Rev. 2002, 102: 3667

<A NAME="RZ17204SS-2">2</A> Peng J. Deng Y. Tetrahedron Lett. 2001, 42: 5917

<A NAME="RZ17204SS-3">3</A> Le Boulaire V. Grée R. Chem. Commun. 2000, 2195

<A NAME="RZ17204SS-4">4</A> Laali KK. Gettwert VJ. J. Fluorine Chem. 2001, 107: 31

<A NAME="RZ17204SS-5">5</A> Song CE. Shim WH. Roh EJ. Lee S.-G. Choi JH. Chem. Commun. 2001, 1122

<A NAME="RZ17204SS-6A">6a</A> Song CE. Shim WH. Roh EJ. Choi JH. Chem. Commun. 2000, 1695

<A NAME="RZ17204SS-6B">6b</A> Stark A. MacLean BL. Singer RD. J. Chem. Soc., Dalton Trans. 1999, 63

<A NAME="RZ17204SS-7">7</A> Earle MJ. McCormac PB. Seddon KR. Chem. Commun. 1998, 2245

<A NAME="RZ17204SS-8">8</A> Wheeler C. West KN. Liotta CL. Eckert CA. Chem. Commun. 2001, 887

<A NAME="RZ17204SS-9">9</A> Gordon CM. McCluskey A. Chem. Commun. 1999, 1431

<A NAME="RZ17204SS-10">10</A> Kabalka GW. Malladi RR. Chem. Commun. 2000, 2191

<A NAME="RZ17204SS-11A">11a</A> Dubreuil JF. Bazureau JP. Tetrahedron Lett. 2000, 41: 7351

<A NAME="RZ17204SS-11B">11b</A> Peng J. Deng Y. New J. Chem. 2001, 25: 639

<A NAME="RZ17204SS-12">12</A> Brasse CC. Englert U. Salzer A. Waffenschmidt H. Wasserscheid P. Organometallics 2000, 19: 3818

<A NAME="RZ17204SS-13">13</A> Mizushima E. Hayashi T. Tanaka M. Green Chem. 2001, 3: 76

<A NAME="RZ17204SS-14">14</A> Ross J. Chen W. Xu L. Xiao J. Organometallics 2001, 20: 138

<A NAME="RZ17204SS-15A">15a</A> Mathews CJ. Smith PJ. Welton T. Chem. Commun. 2000, 1249

<A NAME="RZ17204SS-15B">15b</A> Sirieix J. Oßberger M. Betzemeier B. Knochel P. Synlett 2000, 1613

<A NAME="RZ17204SS-16">16</A> Xu L. Chen W. Xiao J. Organometallics 2000, 19: 1123

<A NAME="RZ17204SS-17A">17a</A> Brown RA. Pollet P. McKoon E. Eckert CA. Liotta CL. Jessop PG. J. Am. Chem. Soc. 2001, 123: 1254

<A NAME="RZ17204SS-17B">17b</A> Chauvin Y. Mussmann L. Olivier H. Angew. Chem., Int. Ed. Engl. 1996, 34: 2698

<A NAME="RZ17204SS-18">18</A> Zim D. De Souza RF. Dupont J. Monteiro AL. Tetrahedron Lett. 1998, 39: 7071

<A NAME="RZ17204SS-19">19</A> Kubisa P. Prog. Polym. Sci. 2004, 29: 3

<A NAME="RZ17204SS-20">20</A> Sémeril D. Olivier-Bourbigou H. Bruneau C. Dixneuf PH. Chem. Commun. 2002, 146

<A NAME="RZ17204SS-21A">21a</A> Schöfer SH. Kaftzik N. Wasserscheid P. Kragl U. Chem. Commun. 2001, 425

<A NAME="RZ17204SS-21B">21b</A> Madeira Lau R. van Rantwijk F. Seddon KR. Sheldon RA. Org. Lett. 2000, 2: 4189

Reviews on NHCs:

<A NAME="RZ17204SS-22A">22a</A> Herrmann WA. Köcher C. Angew. Chem., Int. Ed. Engl. 1997, 36: 2162

<A NAME="RZ17204SS-22B">22b</A> Weskamp T. Böhm VPW. Herrmann WA. J. Organomet. Chem. 2000, 600: 12

<A NAME="RZ17204SS-22C">22c</A> Jafarpour L. Nolan SP. Adv. Organomet. Chem. 2000, 46: 181

<A NAME="RZ17204SS-22D">22d</A> Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290

<A NAME="RZ17204SS-23">23</A> Hillier AC. Grasa GA. Viciu MS. Man Lee H. Yang C. Nolan SP. J. Organomet. Chem. 2002, 653: 69

<A NAME="RZ17204SS-24">24</A> Çetinkaya B. Özdemir I. Bruneau C. Dixneuf PH. J. Mol. Catal. A: Chem. 1997, 118: L1

<A NAME="RZ17204SS-25">25</A> Çetinkaya B. Özdemir I. Dixneuf PH. J. Organomet. Chem. 1997, 534: 153

<A NAME="RZ17204SS-26">26</A> Poyatos M. Mas-Marzá E. Mata JA. Sanaú M. Peris E. Eur. J. Inorg. Chem. 2003, 1215

<A NAME="RZ17204SS-27">27</A> Perry MC. Burgess K. Tetrahedron: Asymmetry 2003, 14: 951

<A NAME="RZ17204SS-28">28</A> Gardiner MG. Herrmann WA. Reisinger C.-P. Schwarz J. Spiegler M. J. Organomet. Chem. 1999, 572: 239

<A NAME="RZ17204SS-29">29</A> Sémeril D. Bruneau C. Dixneuf PH. Adv. Synth. Catal. 2002, 344: 585

<A NAME="RZ17204SS-30">30</A> Fürstner A. Ackermann L. Beck K. Hori H. Koch D. Langemann K. Liebl M. Six C. Leitner W. J. Am. Chem. Soc. 2001, 123: 9000

<A NAME="RZ17204SS-31A">31a</A> Schwarz J. Böhm VPW. Gardiner MG. Grosche M. Herrmann WA. Hieringer W. Raudaschl-Sieber G. Chem. Eur. J. 2000, 6: 1773

<A NAME="RZ17204SS-31B">31b</A> Schürer SC. Gessler S. Buschmann N. Blechert S. Angew. Chem. Int. Ed. 2000, 39: 3898

<A NAME="RZ17204SS-31C">31c</A> Byun J.-W. Lee Y.-S. Tetrahedron Lett. 2004, 45: 1837

<A NAME="RZ17204SS-32A">32a</A> Mayr M. Buchmeiser MR. Wurst K. Adv. Synth. Catal. 2002, 344: 712

<A NAME="RZ17204SS-32B">32b</A> Prühs S. Lehmann CW. Fürstner A. Organometallics 2004, 23: 280

<A NAME="RZ17204SS-32C">32c</A> Çetinkaya B. Gürbüz N. Seçkin T. Özdemir I. J. Mol. Catal. A: Chem. 2002, 184: 31

<A NAME="RZ17204SS-33">33</A> Seddon KR. Stark A. Torres M.-J. Pure Appl. Chem. 2000, 72: 2275

For ¹H NMR data of salts with structures related to those of compounds 3-5, see:

<A NAME="RZ17204SS-34A">34a</A> Herrmann WA. Köcher C. Gooβen LJ. Artus GRJ. Chem. Eur. J. 1996, 2: 1627

<A NAME="RZ17204SS-34B">34b</A> Mata JA. Chianese AR. Miecznikowski JR. Poyatos M. Peris E. Faller JW. Crabtree RH. Organometallics 2004, 23: 1253

<A NAME="RZ17204SS-34C">34c</A> Magill AM. McGuiness DS. Cavell KJ. Britovsek GJP. Gibson VC. White AJP. Williams DJ. White AH. Skelton BW. J. Organomet. Chem. 2001, 617-618: 546

<A NAME="RZ17204SS-34D">34d</A> Dzyuba SV. Bartsch RA. Chem. Commun. 2001, 1466

<A NAME="RZ17204SS-34E">34e</A> Varma RS. Namboodiri VV. Pure Appl. Chem. 2001, 73: 1309

<A NAME="RZ17204SS-34F">34f</A> Yoshida H. Sugiura S. Kunai A. Org. Lett. 2002, 4: 2767

<A NAME="RZ17204SS-35">35</A> Juliá S. Sala P. delMazo J. Sancho M. Ochoa C. Elguero J. Fayet J.-P. Vertut M.-C. J. Heterocycl. Chem. 1982, 19: 1141

<A NAME="RZ17204SS-36">36</A> Note added in proof: A related paper has appeared recently: Gadenne B. Hesemann P. Moreau JJE. Chem. Commun. 2004, 1768