PDF herunterladen
Synlett 2011(5): 659-662  
DOI: 10.1055/s-0030-1259690
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Rasta Resin-DMAP and its Use as a Recyclable Catalyst for the Addition of Carbon Dioxide to Epoxides

Jinni Lu, Patrick H. Toy*
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. of China
Fax: +85228571586; e-Mail: phtoy@hku.hk;
Weitere Informationen

Publikationsverlauf

Received 19 December 2010
Publikationsdatum:
25. Februar 2011 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

Rasta resin-DMAP, a new heterogeneous polystyrene-based amine, has been synthesized and used as a catalyst in addition reactions of carbon dioxide to epoxides to afford cyclic carbonate products. This new material was found to be a more efficient catalyst than divinyl benzene cross-linked polystyrene-supported DMAP, and was readily recovered and reused without significant loss of catalytic activity.

Key words

polymer-supported organocatalyst - polystyrene - DMAP - carbon dioxide - cyclic carbonate

    References and Notes

  • 1 Lu J. Toy PH. Chem. Rev.  2009,  109:  815 
    CrossrefSuche in Google Scholar
  • 2 Hodges JC. Harikrishnan LS. Ault-Justus S. J. Comb. Chem.  2000,  2:  80 
    CrossrefPubMedSuche in Google Scholar
  • 3a Lindsley CW. Hodges JC. Filzen GF. Watson BM. Geyer AG. J. Comb. Chem.  2000,  2:  550 
    Suche in Google Scholar
  • 3b McAlpine SR. Lindsley CW. Hodges JC. Leonard DM. Filzen GF. J. Comb. Chem.  2001,  3:  1 
    Suche in Google Scholar
  • 3c Wisnoski DD. Leister WH. Strauss KA. Zhao Z. Lindsley CW. Tetrahedron Lett.  2003,  44:  4321 
    Suche in Google Scholar
  • 3d Fournier D. Pascual S. Montembault V. Haddleton DM. Fontaine L. J. Comb. Chem.  2006,  8:  522 
    Suche in Google Scholar
  • 3e Fournier D. Pascual S. Montembault V. Fontaine L. J. Polym. Sci., Part A: Polym. Chem.  2006,  44:  5316 
    Suche in Google Scholar
  • 3f Pawluczyk JM. McClain RT. Denicola C. Mulhearn JJ. Rudd DJ. Lindsley CW. Tetrahedron Lett.  2007,  48:  1497 
    Suche in Google Scholar
  • 3g Chen G. Tao L. Mantovani G. Geng J. Nystroem D. Haddleton DM. Macromolecules  2007,  40:  7513 
    Suche in Google Scholar
  • 4 Leung PS.-W. Teng Y. Toy PH. Synlett  2010,  1997 
    Thieme Connect
  • 5 Leung PS.-W. Teng Y. Toy PH. Org. Lett.  2010,  12:  4996 
    CrossrefPubMedSuche in Google Scholar
  • For our work regarding cross-linked polymers, see:
  • 7a Kwok M. Choi W. He HS. Toy PH. J. Org. Chem.  2003,  68:  9831 
    Suche in Google Scholar
  • 7b Zhao LJ. He HS. Shi M. Toy PH. J. Comb. Chem.  2004,  6:  680 
    Suche in Google Scholar
  • 7c Zhao L.-J. Kwong CK.-W. Shi M. Toy PH. Tetrahedron  2005,  61:  12026 
    Suche in Google Scholar
  • For our work regarding noncross-linked polymers, see:
  • 8a Harned AM. He HS. Toy PH. Flynn DL. Hanson PR. J. Am. Chem. Soc.  2005,  127:  52 
    Suche in Google Scholar
  • 8b He HS. Yan JJ. Shen R. Zhuo S. Toy PH. Synlett  2006,  563 
  • 8c Kwong CK.-W. Fu MY. Law HC.-H. Toy PH. Synlett  2010,  2617 
  • 9 Chung CWY. Toy PH. J. Comb. Chem.  2007,  9:  155 
    Suche in Google Scholar
  • 10 Kwong CK.-W. Huang R. Zhang M. Shi M. Toy PH. Chem. Eur. J.  2007,  13:  2369 
    CrossrefPubMedSuche in Google Scholar
  • For selected reviews regarding the addition of carbon dioxide to epoxides to form cyclic carbonates, see:
  • 11a Dai W.-L. Luo S.-L. Yin S.-F. Au C.-T. Appl. Catal., A  2009,  366:  2 
    Suche in Google Scholar
  • 11b Sakakura T. Kohno K. Chem. Commun.  2009,  1312 
  • 11c North M. Pasquale R. Young C. Green Chem.  2010,  12:  1514 
    Suche in Google Scholar
  • For the organocatalytic addition of carbon dioxide to epoxides, see:
  • 12a Shiels RA. Jones CW. J. Mol. Catal. A: Chem.  2007,  261:  160 ; and references cited therein
    Suche in Google Scholar
  • 12b Qi C. Jiang H. Wang Z. Zou B. Yang S. Synlett  2007,  255 
  • 12c Barkakaty B. Morino K. Sudo A. Endo T. Green Chem.  2010,  12:  42 
    Suche in Google Scholar
  • For selected reviews regarding polymer-supported organocatalysts, see:
  • 13a Benaglia M. Puglisi A. Cozzi F. Chem. Rev.  2003,  103:  3401 
    Suche in Google Scholar
  • 13b Benaglia M. New J. Chem.  2006,  30:  1525 
    Suche in Google Scholar
  • 13c Cozzi F. Adv. Synth. Catal.  2006,  348:  1367 
    Suche in Google Scholar
  • 13d Gruttadauria M. Giacalone F. Noto R. Chem. Soc. Rev.  2008,  37:  1666 
    Suche in Google Scholar
  • 13e Kristensen TE. Hansen T. Eur. J. Org. Chem.  2010,  3179 
  • For the use of polymer-supported organocatalysts in the addition of carbon dioxide to epoxides, see:
  • 14a Xie H. Duan H. Li S. Zhang S. New J. Chem.  2005,  29:  1199 
    Suche in Google Scholar
  • 14b Du Y. Wang J.-Q. Chen J.-Y. Cai F. Tian J.-S. Kong D.-L. He L.-N. Tetrahedron Lett.  2006,  47:  1271 
    Suche in Google Scholar
  • 14c Jagtap SR. Raje VP. Samant SD. Bhanage BM. J. Mol. Catal. A: Chem.  2007,  266:  69 
    Suche in Google Scholar
  • 14d Qi C.-R. Jiang H.-F. Wang Z.-Y. Zou B. Chin. J. Chem.  2007,  25:  1051 
    Suche in Google Scholar
  • 14e Qi C. Ye J. Zeng W. Jiang H. Adv. Synth. Catal.  2010,  352:  1925 
    Suche in Google Scholar
  • For the use of other polymers, such as ion-exchange resins, polyaniline salts, and immobilized ionic liquids, to catalyze the addition of carbon dioxide to epoxides, see:
  • 15a Du Y. Cai F. Kong D.-L. He L.-N. Green Chem.  2005,  7:  518 
    Suche in Google Scholar
  • 15b He J. Wu T. Zhang Z. Ding K. Han B. Xie Y. Jiang T. Liu Z. Chem. Eur. J.  2007,  13:  6992 
    Suche in Google Scholar
  • 15c Xie Y. Zhang Z. Jiang T. He J. Han B. Wu T. Ding K. Angew. Chem. Int. Ed.  2007,  46:  7255 
    Suche in Google Scholar
  • 16a Toy PH. Janda KD. Tetrahedron Lett.  1999,  40:  6329 
    Suche in Google Scholar
  • 16b Toy PH. Reger TS. Janda KD. Aldrichimica Acta  2000,  33:  87 
    Suche in Google Scholar
  • 16c Toy PH. Reger TS. Garibay P. Garno JC. Malikayil JA. Liu G.-Y. Janda KD.
    J. Comb. Chem.  2001,  3:  117 
    Suche in Google Scholar
  • 16d Choi MKW. Toy PH. Tetrahedron  2004,  60:  2903 
    Suche in Google Scholar
  • 19 Yue Y. Yu X.-Q. Pu L. Chem. Eur. J.  2009,  15:  5104 
    CrossrefPubMedSuche in Google Scholar
  • 20a Bollini M. González M. Bruno AM. Tetrahedron Lett.  2009,  50:  1507 
    Suche in Google Scholar
  • 20b Ko K. Nakano K. Watanabe S. Ichikawa Y. Kotsuki H. Tetrahedron Lett.  2009,  50:  4025 
    Suche in Google Scholar
  • 20c Deb I. Shanbhag P. Mobin SM. Namboothiri INN. Eur. J. Org. Chem.  2009,  4091 
  • 20d Mhasni O. Rezgui F. Tetrahedron Lett.  2010,  51:  586 
    Suche in Google Scholar
  • 20e Naidu KC. Babu GR. Gangaiah L. Mukkanti K. Madhusudhan G. Tetrahedron Lett.  2010,  51:  1226 
    Suche in Google Scholar
  • 20f Angelini T. Fringuelli F. Lanari D. Pizzo F. Vaccaro L. Tetrahedron Lett.  2010,  51:  1566 
    Suche in Google Scholar
  • 20g Goncalves S. Nicolas M. Wagner A. Baati R. Tetrahedron Lett.  2010,  51:  2348 
    Suche in Google Scholar
  • 20h Aoki S. Kotani S. Sugiura M. Nakajima M. Tetrahedron Lett.  2010,  51:  3547 
    Suche in Google Scholar
  • 20i Hudhomme P. Synlett  2010,  1331 
  • 20j Vuluga D. Legros J. Crousse B. Bonnet-Delpon D. Chem. Eur. J.  2010,  16:  1776 
    Suche in Google Scholar
  • 20k Helou M. Miserque O. Brusson J.-M. Carpentier J.-F. Guillaume SM. Chem. Eur. J.  2010,  16:  13805 
    Suche in Google Scholar
6

Teng, Y.; Toy, P. H. Synlett 2011, 551.

17

See Supporting Information for details.

18

General Procedure for CO 2 Addition Reactions
Epoxide 7a-j (22.4 mmol), CH2Cl2 (0.5 mmol), and 4 (0.224 mmol) were placed in a 25 mL stainless-steel autoclave. Carbon dioxide was then introduced into the reactor at an initial pressure of 20 bar at r.t. The reactor was then heated to 120 ˚C, and the pressure was adjusted to 30 bar. The reaction mixture was stirred under these conditions for the indicated time, and then the autoclave was cooled using an ice bath. After releasing the pressure, compound 4 was filtered off and washed with CH2Cl2. The filtrate was concentrated in vacuo to afford the product 8a-j. The identity of the products was confirmed by ¹H NMR.