Abstract
The development of enantioselective processes involving the use of catalytic species covalently bonded onto polymers and nanoparticles has gained a considerable importance over the last decade, as sustainability concerns have deeply influenced the practice of chemistry. In this review, an overview is given of the different strategies followed for the covalent immobilization of ligand–metal assemblies (for metal catalysis) and catalytic organic molecules (for organocatalysis) onto organic polymers and nanoparticles, paying special attention to the factors that control catalytic activity and enantioselectivity. Efforts devoted to the development of continuous flow processes with immobilized catalysts of these types are also reviewed.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
(a) De Vos DE, Vankelecom IFJ, Jacobs PA (eds) (2000) Chiral catalyst immobilization and recycling. Wiley, Weinheim; (b) Buchmeiser MR (ed) (2003) Polymeric materials in organic synthesis and catalysis. Wiley, Weinheim; (c) Ding K, Uozumi Y (eds) Handbook of asymmetric heterogeneous catalysis. Wiley, Weinheim; (d) Benaglia M (ed) (2008) Recoverable and recyclable catalysts. Wiley, Chichester
For relevant reviews, see: (a) Fan QH, Li YM, Chan ASC (2002) Chem Rev 102:3385–3466; (b) Bräse S, Lauterwasser F, Ziegert RE (2003) Adv Synth Catal 345:869–929; (c) Trindade AF, Gois PMP, Afonso CAM (2009) Chem Rev 109:418–514
(a) Houk KN, List B (eds) (2004) Acc Chem Res 37:631–847; (b) Dalko PI, Moisan L (2004) Angew Chem Int Ed 43:5138–5175; (c) Berkessel A, Gröger H, MacMillan D (eds) (2005) Asymmetric organocatalysis. In: Biomimetic concepts to applications in asymmetric synthesis. Wiley, Weinheim; (d) Koćovský P, Malkov AV (eds) (2006) Tetrahedron 62:243–502; (e) Pellissier H (2007) Tetrahedron 63:9267–9331; (f) List B (ed) (2007) Chem Rev 107:5413–5883; (g) Dondoni A, Massi A (2008) Angew Chem Int Ed 47:4638–4660; (h) MacMillan DWC (2008) Nature 455:304–308
Reviews on supported organocatalysts: (a) Benaglia M, Puglisi A, Cozzi F (2003) Chem Rev 103:3401–3429; (b) Cozzi F (2006) Adv Synth Catal 348:1367–1390; (c) Benaglia M (2006) New J Chem 30:1525–1533; (d) Altava B, Burguete I, Luis SV (2008) Polymer-supported organocatalysts. In: Tulla-Puche J, Albericio F (eds) The power of functional resins in organic synthesis. Wiley, Weinheim
(a) Breslow R (1995) Acc Chem Res 28:146–153; (b) Murakami Y, Kikuchi JI, Hisaeda Y, Hayashida O (1996) Chem Rev 96:721–758; (c) Motherwell WB, Bingham MJ, Six Y (2001) Tetrahedron 57:4663–4686; (d) Breslow R (ed) (2005) Artificial enzymes. Wiley, Weinheim
Lu J, Toy PH (2009) Chem Rev 109:815–838
Fraile JM, García JI, Mayoral JA (2009) Chem Rev 109:360–417
Baker RT, Kobayashi S, Leitner W (2006) Adv Synth Catal 348:1317–1771
Ikegami S, Hamamoto H (2009) Chem Rev 109:583–593
Gruttadauria M, Giacalone F, Noto R (2008) Chem Soc Rev 37:1666–1688
(a) Eder U, Sauer G, Wiechert R (1971) Angew Chem Int Ed Engl 10:496–497; (b) Hajos ZG, Parrish DR (1974) J Org Chem 39:1612–1615
(a) List B, Lerner RA, Barbas III CF (2000) J Am Chem Soc 122:2395–2396; (b) Sakthivel K, Notz W, Bui T, Barbas III CF (2001) J Am Chem Soc 121:5260–5267
Benaglia M, Celentano G, Cozzi F (2001) Adv Synth Catal 343:171–17
Benaglia M, Cinquini M, Cozzi F, Puglisi A, Celentano G (2002) Adv Synth Catal 344:533–542
Benaglia M, Cinquini M, Cozzi F, Puglisi A, Celentano G (2003) J Mol Catal A Chem 204–205:157–163
Gu L, Wu Y, Zhang Y, Zhao G (2007) J Mol Catal A Chem 263(1–2):186–194
Gruttadauria M, Giacalone F, Noto R (2009) Adv Synth Catal 351:33–57
Kondo K, Yamano T, Takemoto K (1985) Makromol Chem 186:1781–1785
Font D, Jimeno C, Pericàs MA (2006) Org Lett 8:4653–4655
Font D, Bastero A, Sayalero S, Jimeno C, Pericàs MA (2007) Org Lett 9:1943–1946
Font D, Sayalero S, Bastero A, Jimeno C, Pericàs MA (2008) Org Lett 10:337–340
Alza E, Rodríguez-Escrich C, Sayalero S, Bastero A, Pericàs MA (2009) Chem Eur J 15:10167–10172
Giacalone F, Gruttadauria M, Marculescu AM, Noto R (2007) Tetrahedron Lett 48:255–259
Dondoni A (2008) Angew Chem Int Ed 47:8995–8997
Gruttadauria M, Giacalone F, Marculescu AM, Lo Meo P, Riela S, Noto R (2007) Eur J Org Chem 4688–4698
Kehat T, Portnoy M (2007) Chem Commun 2823–2825
Moad G, Solomon DH (2006) The chemistry of radical polymerization, 2nd edn. Elsevier, Amsterdam, Boston
Kristensen TE, Vestli K, Fredriksen FK, Hansen FK, Hansen T (2009) Org Lett 11:2968–2971
(a) Andreae MRM, Davis AP (2005) Tetrahedron Aymmetry 16:2487–2492; (b) Akagawa K, Sakamoto S, Kudo K (2005) Tetrahedron Lett 46:8185–8187; (c) Revell JD, Gantenbein D, Krattiger P, Wennemers H (2006) Biopolymers (Pept Sci) 84:105–113; (d) Yan J, Wang L (2008) Synthesis 2065–2072; (e) Carpenter RD, Fettinger JC, Lam KS, Kurth MJ (2008) Angew Chem Int Ed 47:6407–6410
(a) Gruttadauria M, Giacalone F, Marculescu AM, Noto R (2008) Adv Synth Catal 350:1397–1405; (b) Gruttadauria M, Salvo AMP, Giacalone F, Agrigento P, Noto R (2009) Eur J Org Chem 5437–5444
(a) Cobb AJA, Longbottom DA, Shaw DM, Ley SV (2004) Chem Commun 1808–1809; (b) Mitchell CET, Cobb AJA, Ley SV (2005) Synlett 611–614; (c) Luo S, Xu H, Mi X, Li J, Zheng X, Cheng, JP (2006) J Org Chem 71:9244–9247
Alza E, Cambeiro XC, Jimeno C, Pericàs MA (2007) Org Lett 9:3717–3720
Miao T, Wang L (2008) Tetrahedron Lett 49:2173–2176
(a) Palomo C, Mielgo A (2006) Angew Chem Int Ed 45:7876–7880; (b) Lattanzi A (2009) Chem Commun 1452–1463
(a) Varela MC, Dixon SM, Lam KZ, Schore NE (2008) Tetrahedron 64:10087–10090; (b) Röben C, Stasiak M, Janza B, Greiner A, Wendorff JH, Studer A (2008) Synthesis 2163–2168
Alza E, Pericàs MA (2009) Adv Synth Catal 351:3051–3056
(a) Liu YX, Sun YN, Tan HH, Wei L, Tao JC (2007) Tetrahedron Asym 18:2649–2656; (b) Liu Y-X, Sun Y-N, Tan H-H, Tao J-C (2008) Catal Lett 120(3–4):281–287
Luo S, Li J, Zhang L, Xu H, Cheng J-P (2008) Chem Eur J 14:1273–1281
Ahrendt KA, Borths CJ, MacMillan DWC (2000) J Am Chem Soc 122:4243–4244
(a) Lelais G, MacMillan DWC (2006) Aldrichimica Acta 39:79–87; (b) Erkkilä A, Majander I, Pihko PM (2007) Chem Rev 107:5416–5470
Benaglia M, Celentano G, Cinquini M, Puglisi A, Cozzi F (2002) Adv Synth Catal 344:149–152
Puglisi A, Benaglia M, Cinquini M, Cozzi F, Celentano G (2004) Eur J Org Chem 567–573
Selkälä SA, Tois J, Pihko PM, Koskinen AMP (2002) Adv Synth Catal 344:941–945
Haraguchi N, Takemura Y, Itsuno S (2010) Tetrahedron Lett 51:1205–1208
(a) Jacobsen EN, Pfaltz A, Yamamoto H (eds) (1999) Comprehensive asymmetric catalysis, vols I–III. Springer, Berlin; (b) Mikami K, Lautens M (eds) (2007) New frontiers in asymmetric catalysis. Wiley, Hoboken
Dai LX (2004) Angew Chem Int Ed 43:5726–5729
Dioos BML, Vankelecom IVF, Jacobs PA (2006) Adv Synth Catal 348:1413–1446
Saluzzo C, Lamouille T, Hérault D, Lemaire M (2002) Bioorg Med Chem Lett 12:1841–1844
Li Y, Li Z, Li F, Wang Q, Tao F (2005) Org Biomol Chem 3:2513–2518
Arakawa Y, Haraguchi N, Itsuno S (2006) Tetrahedron Lett 47:3229–3243
Liang Y, Jing Q, Li X, Shi L, Ding K (2005) J Am Chem Soc 127:7694–7695
Liang Y, Wang Z, Ding K (2006) Adv Synth Catal 348:1533–1538
Vidal-Ferran A, Bampos N, Moyano A, Pericàs MA, Riera A, Sanders JKM (1998) J Org Chem 63:6309–6318
Vidal-Ferran A, Moyano A, Pericàs MA, Riera A (1997) J Org Chem 62:4970–4982
Minutolo F, Pini D, Petri A, Salvadori P (1996) Tetrahedron Asymmetry 7:2293–2302
Canali L, Cowan E, Deleuze H, Gibson CL, Sherrington DC (1998) Chem Commun 2561–2562
Cho SH, Gadzikwa T, Afshari M, Nguyen ST, Hupp JT (2007) Eur J Inorg Chem 4863–4867
Nielsen M, Thomsen AH, Jensen TR, Jakobsen HJ, Skibsted J, Gothelf KV (2005) Eur J Org Chem 342–347
Song CE, Yang JW, Roh EJ, Lee SG, Ahn JH, Han H (2002) Angew Chem Int Ed 41:3852–3854
Trost BM, Pan Z, Zambrano J, Kujat C (2002) Angew Chem Int Ed 41:4691–4693
(a) Solà L, Reddy KS, Vidal-Ferran A, Moyano A, Pericàs MA, Riera A, Alvarez-Larena A, Piniella JF (1998) J Org Chem 63:7078–7082; (b) Fontes M, Verdaguer X, Solà L, Pericàs MA, Riera A (2004) J Org Chem 69:2532–2543
Pericàs MA, Castellnou D, Rodríguez I, Riera A, Solà L (2003) Adv Synth Catal 345:1305–1313
(a) Castellnou D, Solà L, Jimeno C, Fraile JM, Mayoral JA, Riera A, Pericàs MA (2005) J Org Chem 70:433–438; (b) Castellnou D, Fontes M, Jimeno C, Font D, Solà L, Verdaguer X, Pericàs MA (2005) Tetrahedron 61:12111–12120
(a) Pericàs MA, Herrerías CI, Solà L (2008) Adv Synth Catal 350:927–932; (b) Rolland J, Cambeiro XC, Rodríguez-Escrich C, Pericàs MA (2009) Beilstein J Org Chem 5:56
Fraile JM, Mayoral JA, Serrano J, Pericàs MA, Solà L, Castellnou D (2003) Org Lett 5:4333–4335
Bastero A, Font D, Pericàs MA (2007) J Org Chem 72:2460–2468
(a) Burguete MI, Díez-Barra E, Fraile JM, García JI, García-Verdugo E, González R, Herrerías CI, Luis SV, Mayoral JA (2002) Bioorg Med Chem Lett 12:1821–1824; (b) Díez-Barra E, Fraile JM, García JI, Garcia-Verdugo E, Herrerías CI, Luis SV, Mayoral JA, Sánchez-Verdú P, Tolosa J (2003) Tetrahedron Asymmetry 14:773–778; (c) Burguete MI, Fraile JM, García JI, García-Verdugo E, Luis SV, Mayoral JA (2000) Org Lett 2:3905–3908
Mandoli A, Orlandi S, Pini D, Salvadori P (2003) Chem Commun 2466–2467
Werner H, Herrerías CI, Glos M, Gissibl A, Fraile JM, Pérez I, Mayoral JA, Reiser O (2006) Adv Synth Catal 348:125–132
(a) Uozumi Y, Danjo H, Hayashi T (1998) Tetrahedron Lett 39:8303–8306; (b) Hocke H, Uozumi Y (2004) Tetrahedron 60:9297–9306
(a) Uozumi Y, Shibatomi K (2001) J Am Chem Soc 123:2919–2920; (b) Nakai Y, Uozumi Y (2005) Org Lett 7:291–293; (c) Uozumi Y, Kimura M (2006) Tetrahedron: Asymmetry 17:161–166
Uozumi Y, Tanaka H, Shibatomi K (2004) Org Lett 6:281–283
Zhao D, Sun J, Ding K (2004) Chem Eur J 10:5952–5963
Popa D, Marcos R, Sayalero S, Vidal-Ferran A, Pericàs MA (2009) Adv Synth Catal 351:1539–1556
(a) Astruc D (ed) (2007) Nanoparticles and catalysis, Wiley, Weinheim; (b) Abbet S, Heiz U (2004) In: Rao CNR, Müller A, Cheetham AK (eds) The chemistry of nanomaterials, vol 2, ch. 17. Wiley, Weinheim; (c) Klabunde KJ, Mulukutla RS (2001) In: Klabunde KJ (ed) Nanoscale materials in chemistry, ch. 7. Wiley, New York
(a) Somorjai GA, Park JY (2008) Angew Chem Int Ed 47:9212–9228; (b) Somorjai GA, Contreras AM, Montano M, Rioux RM (2006) Clusters, surfaces, and catalysis. PNAS 103:10577–10583; (c) Astruc D, Lu F, Aranzaes JR (2005) Angew Chem Int Ed 44:7852–7872; (d) Park KH, Chung YK (2005) Synlett 545–559; (e) Grunes J, Zhu J, Somorjai GA (2003) Chem Commun 2257–2260; (f) Pasquato L, Pengo P, Scrimin P (2004) J Mater Chem 14:3481–3487; (g) Moreno-Mañas M, Pleixats R (2003) Acc Chem Res 36:638–643
(a) Tang BX, Guo SM, Zhang MB, Li JH (2008) Synthesis 1707–1716; (b) Kantam ML, Yadav J, Laha S, Sreedhar B, Jha S (2007) Adv Synth Catal 349:1938–1942; (c) Rout L, Jammi S, Punniyamurthy T (2007) Org Lett 9:3397–3399
(a) Rout L, Sen TK, Punniyamurthy T (2007) Angew Chem Int Ed 46:5583–5586; (b) Ranu BC, Saha A, Jana R (2007) Adv Synth Catal 349:2690–2696
Zhang J, Zhang Z, Wang Y, Zheng X, Wang Z (2008) Eur J Org Chem 5112–5116
(a) Rossi LM, Machado G (2009) J Mol Cat A Chem 298:69–73; (b) Maity P, Basu S, Bhaduri S, Lahiri GK (2007) Adv Synth Catal 349:1955–1962
Studer M, Blaser HU, Exner C (2003) Adv Synth Catal 345:45–65
(a) Tamura M, Fujihara H (2003) J Am Chem Soc 125:15742–15743; (b) Jansat S, Gómez M, Philippot K, Muller G, Guiu E, Claver C, Castillon S, Chaudret B (2004) J Am Chem Soc 126:1592–1593; (c) Sawai K, Tatumi R, Nakahodo T, Fujihara H (2008) Angew Chem Int Ed 47:6917–6919; (d) Park KH, Chung YK (2005) Adv Synth Catal 347:854–866; (e) Choudary BM, Ranganath KVS, Pal U, Kantam ML, Sreedhar B (2005), J Am Chem Soc 127:13167–13171
For a recent review, see: Roy S, Pericàs MA (2009) Org Biomol Chem 7:2669–2677
Li H, Luk YY, Mrksich M (1999) Langmuir 15:4957–4959
Marubayashi K, Takizawa S, Kawakusu T, Arai T, Sasai H (2003) Org Lett 5:4409–4412
Belser T, Stohr M, Pfaltz A (2005) J Am Chem Soc 127:8720–8731
Ono F, Kanemasa S, Tanaka J (2005) Tetrahedron Lett 46:7623–7626
Belser T, Jacobsen EN (2008) Adv Synth Catal 350:967–971
Gardimalla HMR, Mandal D, Stevens PD, Yen M, Gao Y (2005) Chem Commun 4432–4434
Hu A, Yee GT, Lin W (2005) J Am Chem Soc 127:12486–12487
Michalek F, Lagunas A, Jimeno C, Pericàs MA (2008) J Mater Chem 18:4692–4697
(a) Pastó M, Riera A, Pericàs MA (2002) Eur J Org Chem 2337–2341; (b) Alza E, Bastero A, Jansat S, Pericàs MA (2008) Tetrahedron Asymmetry 19:374–378
Li J, Zhang Y, Han D, Gao Q, Li C (2009) J Mol Cat A Chem 298:31–35
Luo S, Zheng X, Cheng JP (2008) Chem Commun 5719–5721
Jiang Y, Guo C, Xia H, Mahmood I, Liu H (2008) Ind Eng Chem Res 47:9628–9635
Helms B, Fréchet JMJ (2006) Adv Synth Catal 348:1125–1148
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2010 Springer Netherlands
About this chapter
Cite this chapter
Jimeno, C., Sayalero, S., Pericàs, M.A. (2010). Covalent Heterogenization of Asymmetric Catalysts on Polymers and Nanoparticles. In: Barbaro, P., Liguori, F. (eds) Heterogenized Homogeneous Catalysts for Fine Chemicals Production. Catalysis by Metal Complexes, vol 33. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-3696-4_4
Download citation
DOI: https://doi.org/10.1007/978-90-481-3696-4_4
Published:
Publisher Name: Springer, Dordrecht
Print ISBN: 978-90-481-3695-7
Online ISBN: 978-90-481-3696-4
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)