Skip to main content

Chemoselective and Enantioselective Hydrogenations on Immobilized Complexes

  • Chapter
  • First Online:
Heterogenized Homogeneous Catalysts for Fine Chemicals Production

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 33))

Abstract

Homogeneous catalysts, which are mixed with the reactants at the molecular level, typically show the highest activity and selectivity as they offer chemically well-defined active sites and are not limited by heat and mass transport. However, an inherent disadvantage of the homogeneous catalysis is the need to separate the catalyst from a product after the reaction. Therefore, solid or immobilized homogeneous catalysts are preferred in industry. In this contribution we pay attention to chemoselectivity, regioselectivity and enantioselectivity in the synthesis of fine chemicals by means of hydrogenation reactions with immobilised homogeneous complexes. Preferential hydrogenation of one functional group in a molecule over another is the chemoselective process, while regioselective hydrogenation is the preferential formation of one constitutional isomer of the product in a reaction in which other isomers may also be formed, and the stereoselective hydrogenation is the formation of an excess of one stereoisomer over others. Homogeneous and heterogeneous catalytic transfer hydrogenations (CTH) were additionally introduced as alternative methods to the classical hydrogenation processes. They utilise a different hydrogen source from molecular hydrogen and can find their use for reduction of any type of groups.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Gallezot P, Richard D (1998) Catal Rev-Sci Eng 40:81–126

    Article  CAS  Google Scholar 

  2. Fache E, Mercier C, Pagnier N et al (1993) J Mol Catal A Chem 79:117–131

    CAS  Google Scholar 

  3. James BR, Morris RH (1978) J Chem Soc. Chem Commun 21:929–930

    Google Scholar 

  4. Joó F, Kovács J, Bényei A et al (1998) Angew Chem Int Ed 37:969–970

    Article  Google Scholar 

  5. Zsigmond A, Balatoni I, Bogár K et al (2004) J Catal 227:428–435

    Article  CAS  Google Scholar 

  6. Augustine RL, Tanielyan SK, Mahata N et al (2003) Appl Catal. A 256:69–76

    CAS  Google Scholar 

  7. End N, Schoning KU (2004) Top. Curr Chem 242:241–271

    Article  CAS  Google Scholar 

  8. Augustine RL, Tanielyan SK, Anderson S et al (1999) Chem Commun 13:1257–1258

    Article  Google Scholar 

  9. Ghosh A, Kumar R (2005) Microporous Mesoporous Mater 87:33–44

    Article  CAS  Google Scholar 

  10. Sephard DS, Zhou W, Maschmeyer T et al (1998) Angew Chem Int Ed 37:2719–2723

    Article  Google Scholar 

  11. Thomas JM, Raja R (2004) J Organomet Chem 689:4110–4124

    Article  CAS  Google Scholar 

  12. Noyori R, Ohkuma T (2001) Angew Chem Int Ed 40:40–73

    Article  CAS  Google Scholar 

  13. Nunes RMD, Fernandes TF, Carvalho GA et al (2009) J Mol Catal A Chem 307:115–120

    Article  CAS  Google Scholar 

  14. Guoyu Y, Ailing S, Wenfeng Z, Hainin Z, Denggao J (2007) Catal Lett 118:275–279

    Article  CAS  Google Scholar 

  15. Ernst S, Disteldorf H, Yang X (1998) Microporous Mesoporous Mater 22:457–464

    Article  CAS  Google Scholar 

  16. Arstad E, Barrett AGM, Tedeschi L (2003) Tetrahedron Lett 44:2703–2707

    Article  CAS  Google Scholar 

  17. Buchmeiser MR (2000) Chem Rev 100:1565–1604

    Article  CAS  Google Scholar 

  18. Barrett AGM, Hopkins BT, Kobberling J (2002) Chem Rev 102:3301–332

    Article  CAS  Google Scholar 

  19. Barrett AGM, Hopkins BT, Kobberling J (2002) J Org Letters 4:1975–1977

    Article  CAS  Google Scholar 

  20. Horvath HH, Papp G, Csajagi C et al (2007) Catal Commun 8:442–446

    Article  CAS  Google Scholar 

  21. Horvath HH, Joo F (2005) React Kinet Catal Lett 85:355–360

    Article  CAS  Google Scholar 

  22. Zsigmond A, Undrala S (2007) Notheisz, Papp G, Joo F. Catal Lett 15:163–168

    Article  CAS  Google Scholar 

  23. Burke SD, Danheiser RL (1999) Handbook of reagents for organic synthesis. Wiley, New York

    Google Scholar 

  24. Ohkuma T, Ooka H, Hashiguchi S et al (1995) J Am Chem Soc 117:2675–2676

    Article  CAS  Google Scholar 

  25. Baratta W, Herdtweck E, Siega K et al (2005) Organometallics 24:1660–1669

    Article  CAS  Google Scholar 

  26. Choualeb A, Lough AJ, Gusev DG (2007) Organometallics 26:5224–5229

    Article  CAS  Google Scholar 

  27. Schrock RR, Osborn JA (1970) Chem Commun 9:567–568

    Google Scholar 

  28. Deshmukh AA, Kinage AK, Kumar R (2008) Catal Lett 120:257–260

    Article  CAS  Google Scholar 

  29. Steines S, Englert U, Driessen-Hoelscher B (2000) Chem Commun 3:217–218

    Article  Google Scholar 

  30. Leitmannova E, Cerveny L (2007) J Mol Catal A Chem 261:242–245

    Article  CAS  Google Scholar 

  31. Sahoo S, Kumar P, Lefebvre F et al (2007) J Mol Catal A Chem 273:102–108

    Article  CAS  Google Scholar 

  32. Bronowski J (1973) The ascent of man. British Broadcasting Corporation Publishers Series, London

    Google Scholar 

  33. Cerna I, Kluson P, Drobek M et al (2007) Chem Listy 101:994–1001

    CAS  Google Scholar 

  34. Noyori R (1994) Asymmetric catalysis in organic synthesis. Wiley-Interscience, New York

    Google Scholar 

  35. Von Moos R, Stolz R, Cerny T et al (2003) Swiss Med Weekly 133:77–87

    Google Scholar 

  36. Monteiro AL, Zinn FK, De Souza RF et al (1997) Tetrahedron Asym 8:177–179

    Article  CAS  Google Scholar 

  37. Pino P, Consiglio G (1979) Fundam Res Homogen Catal 3:519–536

    Article  CAS  Google Scholar 

  38. Fan Q-H, Chen Y-M, Chen X-M et al (2000) Chem Commun 789–790

    Google Scholar 

  39. Noyori R (1994) Tetrahedron 50:4259–4292

    Article  CAS  Google Scholar 

  40. Akutagawa S (1995) Appl Catal A 128:171–207

    Article  CAS  Google Scholar 

  41. Fry SE, Pienta NJ (1985) J Am Chem Soc 107:6399–6400

    Article  CAS  Google Scholar 

  42. Noyori R (2001) Les Prix Nobel, 186 (http://nobelprizes.com/nobel/)

  43. Knowles WS (2001) Prix Nobel, 160 (http://nobelprizes.com/nobel/)

  44. Sharpless KB (2001) Prix Nobel, 225 (http://nobelprizes.com/nobel/)

  45. Onitsuka K, Ajioka Y, Matsushima Y et al (2001) Organometallics 20:3274–3282

    Article  CAS  Google Scholar 

  46. Sugimura T (1999) Catal Surv Jpn 3:37–42

    Article  CAS  Google Scholar 

  47. Shimazu S, Ro K, Sento T, Ichikuni N, Uematsu T (1996) J Mol Catal A 107:297–303

    Article  CAS  Google Scholar 

  48. Blaser HU (1991) Tetrahedron Asym 2:843–849

    Article  CAS  Google Scholar 

  49. Keane MA (1994) Can J Chem 72:372–380

    Article  CAS  Google Scholar 

  50. Nitta Y, Imanaka T, Teranishi S (1983) J Catal 80:31–39

    Article  CAS  Google Scholar 

  51. Osawa T, Mita S, Iwai A et al (2000) J Mol Catal A Chem 157:207–216

    Article  CAS  Google Scholar 

  52. Yasumori I, Yokozeki M, Inoue Y (1981) Faraday Discuss Chem Soc 72:385–396

    Article  Google Scholar 

  53. Osawa T, Harada T (1984) Bull Chem Soc Jpn 57:1518–1521

    Article  CAS  Google Scholar 

  54. Izumi Y, Imaida M, Fukawa H et al (1963) Bull Chem Soc Jpn 21

    Google Scholar 

  55. Keane MA (1994) Langmuir 10:4560–4565

    Article  CAS  Google Scholar 

  56. Bennett A, Christie S, Keane MA et al (1991) Catal Today 10:363–370

    Article  CAS  Google Scholar 

  57. Tani K, Yamagata T, Otsuka S et al (1989) Org Synth 67:33–43

    CAS  Google Scholar 

  58. Noe CR, Weigand A, Pirker S et al (1997) Monatsh Chem 128:301–316

    Article  CAS  Google Scholar 

  59. Noe CR, Weigand A, Pirker S (1996) Monatsh Chem 127:1081–1097

    Article  CAS  Google Scholar 

  60. Carrea G, Colonna S, Meek AD et al (2004) Tetrahedron Asym 15:2945–2949

    Article  CAS  Google Scholar 

  61. Benhamza R, Amrani Y, Sinou D (1985) J Organomet Chem 288:C37–C39

    Article  CAS  Google Scholar 

  62. Jessop PG, Morris RH (1992) Coord Chem Rev 121:155–284

    Article  CAS  Google Scholar 

  63. Brunner H, Muschiol M, Wischert T et al (1990) Tetrahedron Asym 1:159–162

    Article  CAS  Google Scholar 

  64. Osawa T, Harada T, Tai A et al (1997) Stud Surf Sci Catal 108:199–206

    Article  CAS  Google Scholar 

  65. Keane MA, Webb G (1992) J Catal 136:1–15

    Article  CAS  Google Scholar 

  66. Tani K, Yamagata T, Otsuka S et al (1982) J Chem Soc, Chem Commun 600–601

    Google Scholar 

  67. Tani K, Yamagata T, Akutagawa S et al (1984) J Am Chem Soc 106:5208–5217

    Article  CAS  Google Scholar 

  68. Otsuka S, Tani K (1985) Asymmetric Synth 5:171–191

    CAS  Google Scholar 

  69. Genet JP (2003) Acc Chem Res 36:908

    Article  CAS  Google Scholar 

  70. Noyori R, Kitamura M (1989) Modern Synthetic Methods 5:115

    Article  CAS  Google Scholar 

  71. Noyori R (2003) Adv Synth Catal 345:15–32

    Article  CAS  Google Scholar 

  72. Sharpless KB (1985) Chemtech 15:692–700

    CAS  Google Scholar 

  73. Sharpless KB (2002) Angew Chem. Int Ed 41:2024–2032

    Article  CAS  Google Scholar 

  74. Abdur-Rashid K, Faatz M, Lough AJ et al (2001) J Am Chem Soc 123:7473–7474

    Article  CAS  Google Scholar 

  75. Shao L, Takeuchi K, Ikemoto M et al (1992) J Organomet Chem 435:133–147

    Article  CAS  Google Scholar 

  76. Chauvin Y, Commereuc D, Stern R (1978) J Organomet Chem 146:311–318

    Article  CAS  Google Scholar 

  77. De Araujo MP, Valle EMA, Ellena J et al (2004) Polyhedron 23:3163–3172

    Article  CAS  Google Scholar 

  78. Hobbs CF, Knowles WS (1981) J Org Chem 46:4422–4427

    Article  CAS  Google Scholar 

  79. Noyori R, Ohta M, Hsiao Y et al (1986) J Am Chem Soc 108:7117–7119

    Article  CAS  Google Scholar 

  80. Kitamura M, Tokunaga M, Noyori R (1992) J Org Chem 57:4053–4054

    Article  CAS  Google Scholar 

  81. Takaya H, Ohta T, Inoue S-I (1995) Org Synth 72:74–85

    CAS  Google Scholar 

  82. Ohta T, Takaya H, Noyori R (1990) Tetrahedron Lett 31:7189–7192

    Article  CAS  Google Scholar 

  83. Pu L (1998) Tetrahedron Asym 9:1457–1461

    Article  CAS  Google Scholar 

  84. Halpern J (1983) Pure Appl Chem 55:99–106

    Article  CAS  Google Scholar 

  85. Knowles WS (2003) Adv Synth Catal 345:3–13

    Article  CAS  Google Scholar 

  86. Miyashita A, Yasuda A, Takaya H et al (1980) J Am Chem Soc 102:7932–7934

    Article  CAS  Google Scholar 

  87. Miyashita A, Takaya H, Souchi T et al (1984) Tetrahedron 40:1245–1253

    Article  CAS  Google Scholar 

  88. Brown KJ, Berry MS, Waterman KC et al (1984) J Am Chem Soc 106:4717–4723

    Article  CAS  Google Scholar 

  89. Takaya H, Mashima K, Koyano K et al (1986) J Org Chem 51:629–635

    Article  CAS  Google Scholar 

  90. Knowles WS, Sabacky MJ (1968) Chem Commun 22:1445–1446

    Google Scholar 

  91. Osborn JA, Jardine FH, Young JF et al (1966) J Chem Soc A Inorg Phys Theoret 1711–1732

    Google Scholar 

  92. Richards CJ, Locke AJ (1998) Tetrahedron Asym 9:2377–2381

    Article  CAS  Google Scholar 

  93. Korpiun O, Mislow K (1967) J Am Chem Soc 89:4784–4786

    Article  CAS  Google Scholar 

  94. Knowles WS, Sabacky MJ, Vineyard BD (1970) Ann N Y Acad Sci 172:232–237

    Article  CAS  Google Scholar 

  95. Morrison JD, Burnett RE, Aguiar AM et al (1971) J Am Chem Soc 93:1301–1303

    Article  CAS  Google Scholar 

  96. Knowles WS, Sabacky MJ, Vineyard BD (1977) (Monsanto Co., USA). Int. Pat. Appl.: US 75-602484/4005127; Chem Abstr AN 1977:190463

    Google Scholar 

  97. Perry MC, Burgess K (2003) Tetrahedron Asym 14:951–956

    Article  CAS  Google Scholar 

  98. Taber DF, Silverberg LJ (1991) Tetrahedron Lett 32:4227–4230

    Article  CAS  Google Scholar 

  99. Hoke JB, Hollis LS, Stern EW (1993) J Organomet Chem 455:193–196

    Article  CAS  Google Scholar 

  100. Ikariya T, Ishii Y, Kawano H et al (1985) J Chem Soc. Chem Commun 13:922–924

    Google Scholar 

  101. King SA, Thompson AS, King AO et al (1992) J Org Chem 57:6689–6691

    Article  CAS  Google Scholar 

  102. Kawano H, Ishii Y, Ikariya T et al (1987) Tetrahedron Lett 28:1905–1908

    Article  CAS  Google Scholar 

  103. Abdur-Rashid K, Lough AJ, Morris RH (2001) Organometallics 20:1047–1049

    Article  CAS  Google Scholar 

  104. Ohkuma T, Koizumi M, Doucet H et al (1998) J Am Chem Soc 120:13529–13530

    Article  CAS  Google Scholar 

  105. Wolfson A, Vankelecom IFJ, Geresh S et al (2003) J Mol Catal A Chem 198:39–45

    Article  CAS  Google Scholar 

  106. Mashima K, Kusano K-H, Sato N et al (1994) J Org Chem 59:3064–3076

    Article  CAS  Google Scholar 

  107. Pavlov VA, Starodubtseva EV, Vinogradov MG et al (2000) Russ Chem Bull 49:725–728

    Article  Google Scholar 

  108. Wolfson A, Vankelecom IFJ, Geresh S et al (2004) J Mol Catal A Chem 217:21–26

    Article  CAS  Google Scholar 

  109. Bartek L, Drobek M, Kuzma M et al (2005) Catal Commun 6:61–65

    Article  CAS  Google Scholar 

  110. Cornils B, Herrmann WA (1996) Appl Homogen Catal Organomet Compounds 2:575–601

    CAS  Google Scholar 

  111. Palmer MJ (1999) Will M 10:2045–2049

    CAS  Google Scholar 

  112. Sellner H, Faber C, Rheiner PB et al (2000) Chem-Eur J 6:3692–3705

    Article  CAS  Google Scholar 

  113. Itsuno S, Frechet JMJ (1987) J Org Chem 52:4140–4142

    Article  CAS  Google Scholar 

  114. Herrmann WA, Cornils B (1996) Appl Homogen Catal Organomet Compounds 2:1167–1197

    Article  CAS  Google Scholar 

  115. Wynberg H (1982) Chemtech 12:116–121

    CAS  Google Scholar 

  116. Annis DA, Jacobsen EN (1999) J Am Chem Soc 121:4147–4154

    Article  CAS  Google Scholar 

  117. Nagel U, Kinzel E (1986) J Chem Soc Chem Commun 14:1098–1099

    Article  Google Scholar 

  118. Pugin B (1996) J Mol Catal A Chem 107:273–279

    Article  CAS  Google Scholar 

  119. Mollmann E, Tomlinson P, Holderich WF (2003) J Mol Catal A Chem 206:253–259

    Article  CAS  Google Scholar 

  120. De Vos DE, Jacobs PA (2000) Catal Today 57:105–114

    Article  Google Scholar 

  121. De Vos DE, Sels BF, Jacobs PA (2001) Adv Catal 46:1–87

    Article  Google Scholar 

  122. Sabater MJ, Corma A, Domenech A et al (1997) Chem Commun 14:1285–1286

    Article  Google Scholar 

  123. Adima A, Moreau JJE, Man MWC (1997) J Mater Chem 7:2331–2333

    Article  CAS  Google Scholar 

  124. Vankelecom IFJ, Tas D, Parton RF et al (1996) Angew Chem. Int Ed 35:1346–1348

    Article  CAS  Google Scholar 

  125. Tas D, Thoelen C, Vankelecom IFJ (1997) Chem Commun 23:2323–2324

    Article  Google Scholar 

  126. Bayston DJ, Fraser JL, Ashton MR et al (1998) Org Chem 63:3137–3140

    Article  CAS  Google Scholar 

  127. Ohkuma T, Takeno H, Honda Y et al (2001) Adv Synth Catal 343:369–375

    Article  CAS  Google Scholar 

  128. Q-h F, C-y R, C-h Y et al (1999) J Am Chem Soc 121:7407–7408

    Article  CAS  Google Scholar 

  129. Fan Q-H, Chen Y-M, Chen X-M et al (2000) Chem Commun 9:789–790

    Article  Google Scholar 

  130. Fan QH, Deng GJ, Lin CC et al (2001) Tetrahedron Asym 12:1241–1247

    Article  CAS  Google Scholar 

  131. Yu H-B, Hu Q-S, Pu L (2000) Tetrahedron Lett 41:1681–1685

    Article  CAS  Google Scholar 

  132. Ohkuma T, Doucet H, Pham T et al (1998) J Am Chem Soc 120:1086–1087

    Article  CAS  Google Scholar 

  133. Lamouille T, Saluzzo C, ter Halle R et al (2001) Tetrahedron Lett 42:663–664

    Article  CAS  Google Scholar 

  134. Lemaire M, Ter Halle R, Schulz E, Colasson B, Spagnol M, Saluzzo C, Lamouille T (2000) (Rhodia Chimie, Fr.; Centre National de la Recherche Scientifique (C.N.R.S.)). Int Pat Appl: WO 2000-FR82/2000052081; Chem Abstr AN 2000:628204

    Google Scholar 

  135. Wan KT, Davis ME (1995) J Catal 152:25–30

    Article  CAS  Google Scholar 

  136. Van Brussel W, Renard M, Tas D, Rane VH, Parton R, Jacobs PA (1997) (K.U. Leuven Research & Development, Belg.; Van Brussel, Willy; Renard, Michel; Tas, Diedrik; Rane, Vilas Hare; Parton, Rudy; Jacobs, Pierre A.). Int Pat Appl: WO 96-BE108/9714500; Chem Abstr AN 1997:380998

    Google Scholar 

  137. Tas D, Jeanmart D, Parton RF et al (1997) Stud Surf Sci Catal 108:493–500

    Article  CAS  Google Scholar 

  138. Tanielyan SK, Augustine RL (1998) Chem Ind 75:101–1107

    CAS  Google Scholar 

  139. Barnard FJCh, Rouzaud J, Stevenson SH (2005) Org Process Res Dev 9:164–167

    Article  CAS  Google Scholar 

  140. Augustine RL, Goel P, Mahata N et al (2004) J Mol Catal A Chem 216:189–197

    Article  CAS  Google Scholar 

  141. Bartek L, Kluson P (2004) Chem Listy 98:157–167

    Google Scholar 

  142. Bartek L, Kluson P – unpublished results

    Google Scholar 

  143. Floris T, Kluson P, Pelantova H et al (2009) Appl Catal. A 366:160–165

    CAS  Google Scholar 

  144. Reichardt C (1988) Solvents and solvent effects in organic chemistry, 2nd edn. VCH Verlagsgesellschaft, Weinheim

    Google Scholar 

  145. Senapati S, Chandra A (2001) J Phys Chem B 105:5106–5109

    Article  CAS  Google Scholar 

  146. Zhu K, He H, Xie S et al (2003) Chem Phys Lett 377:317–321

    Article  CAS  Google Scholar 

  147. Welton T (2004) Coord Chem Rev 248:2459–2477

    Article  CAS  Google Scholar 

  148. Welton T (1999) Chem Rev 99:2071–2084

    Article  CAS  Google Scholar 

  149. Wasserscheid P, Gordon CM, Hilgers C (2001) Chem Commun 13:1186–1187

    Article  Google Scholar 

  150. Welton T (2008) Green Chem 10:483

    Article  CAS  Google Scholar 

  151. Welton T (2004) Phys Chem Chem Phys 6:3280–3285

    Article  CAS  Google Scholar 

  152. Hintermair U, Gutel T, Slawin AMZ et al (2008) J Organomet Chem 693:2407–2414

    Article  CAS  Google Scholar 

  153. Ochsner E, Etzold B, Junge K et al (2009) Adv Synth Catal 351:235–245

    Article  CAS  Google Scholar 

  154. Gabriel S (1888) Ber Deutsch Chem Ges 21:566

    Article  CAS  Google Scholar 

  155. Walden P (1914) Bull Acad Sci St. Petersburg 405–422

    Google Scholar 

  156. Earle MJ, McCormac PB, Seddon KR (1999) Green Chem 1:23–25

    Article  CAS  Google Scholar 

  157. Chen X, Li X, Hu A et al (2008) Tetrahedron Asym 19:1–14

    Article  CAS  Google Scholar 

  158. Ni B, Headley AD et al (2006) Tetrahedron Lett 47:7331–7334

    Article  CAS  Google Scholar 

  159. Luo SP, Xu DQ, Yue HD (2006) Tetrahedron Asym 17:2028–2023

    Article  CAS  Google Scholar 

  160. Ding J, Armstrong DW (2005) Chirality 17:281–292

    Article  CAS  Google Scholar 

  161. Jodry JJ, Mikami K (2004) Tetrahedron Lett 45:4429–4431

    Article  CAS  Google Scholar 

  162. Ishida Y, Miyauchi H, Saigo K (2002) Chem Commun 2240–2241

    Google Scholar 

  163. Ghatee MH, Zolghadr AR (2008) Fluid Phase Equilib 263:168–175

    Article  CAS  Google Scholar 

  164. Pârvulescu VI, Hardacre C (2007) Chem Rev 107:2615–2665

    Article  CAS  Google Scholar 

  165. Wilkes JS, Zaworotko MJ (1992) J Chem Soc Chem Commun 965–966

    Google Scholar 

  166. Weyershausen B, Lehmann K (2005) Green Chem 7:15–19

    Article  CAS  Google Scholar 

  167. Wilkes JS (2002) Green Chem 4:73–80

    Article  CAS  Google Scholar 

  168. Greaves TL, Drummond CJ (2008) Chem Rev 108:206–237

    Article  CAS  Google Scholar 

  169. Ohta T, Takaya H, Kitamura M, Nagai K, Noyori R (1987) J Org Chem 52:3174–3176

    Article  CAS  Google Scholar 

  170. Wasserscheid P, Keim W (2000) Angew Chem. Int Ed 39:3772–3789

    CAS  Google Scholar 

  171. Baudequin C, Baudoux J, Levillain J et al (2003) Tetrahedron Asym 14:3081–3093

    Article  CAS  Google Scholar 

  172. Boon JA, Levisky JA, Pflug JL et al (1986) J Org Chem 51:480–483

    Article  CAS  Google Scholar 

  173. Chauvin Y, Gilbert B, Guibard I (1990) J Chem Soc. Chem Commun 23:1715–1716

    Google Scholar 

  174. Guernik S, Wolfson A, Herskowitz M et al (2001) Chem Commun 22:2314–2315

    Article  CAS  Google Scholar 

  175. Berger A, de Souza RF, Delgado MR et al (2001) Tetrahedron Asym 12:1825–1828

    Article  CAS  Google Scholar 

  176. Liu F, Abrams MB, Baker RT et al (2001) Chem Commun 5:433–434

    Article  CAS  Google Scholar 

  177. Brown RA, Pollet P, McKoon E et al (2001) J Am Chem Soc 123:1254–1255

    Article  CAS  Google Scholar 

  178. Jessop PG, Stanley RR, Brown RA et al (2003) Green Chem 5:123–128

    Article  CAS  Google Scholar 

  179. Wolfson A, Vankelecom IFJ, Jacobs PA (2003) Tetrahedron Lett 44:1195–1198

    Article  CAS  Google Scholar 

  180. Burk MJ, Feng S, Gross MF et al (1995) J Am Chem Soc 117:8277–8278

    Article  CAS  Google Scholar 

  181. Xiao J, Nefkens SCA, Jessop PG (1996) Tetrahedron Lett 37:2813–2816

    Article  CAS  Google Scholar 

  182. Uemura T, Zhang X, Matsumura K et al (1996) J Org Chem 61:5510–5516

    Article  CAS  Google Scholar 

  183. Jessop PG, Ikariya T, Noyori R (1999) Chem Rev 99:475–493

    Article  CAS  Google Scholar 

  184. Sheldon R (2001) Chem Commun 23:2399–2407

    Article  CAS  Google Scholar 

  185. Finotello A, Bara JE, Narayan S et al (2008) J Phys Chem B 112:2335–2339

    Article  CAS  Google Scholar 

  186. Olivier-Bourbigou H, Magna L (2002) J Mol Catal A Chem 182:419–437

    Article  Google Scholar 

  187. McLean AJ, Muldoon MJ, Gordon CM et al (2002) Chem Commun 17:1880–1881

    Article  CAS  Google Scholar 

  188. Anthony JL, Maginn EJ, Brennecke JF (2002) J Phys Chem B 106:7315–7320

    Article  CAS  Google Scholar 

  189. Talaty ER, Raja S, Storhaug VJ et al (2004) J Phys Chem B 108:13177–13184

    Article  CAS  Google Scholar 

  190. Chaudhari RV, Bhanage BM, Deshpande RM et al (1995) Nature 373:501–503

    Article  CAS  Google Scholar 

  191. Gordon CM (2001) Appl Catal A 222:101–117

    Article  CAS  Google Scholar 

  192. Cammarata L, Kazarian SG, Salter PA et al (2001) Phys Chem Chem Phys 3:5192–5200

    Article  CAS  Google Scholar 

  193. Wolfson A, Vankelecom IFJ, Jacobs PA (2005) J Organomet Chem 690:3558–3566

    Article  CAS  Google Scholar 

  194. Crosthwaite JM, Muldoon MJ, Aki SNVK et al (2006) J Phys Chem B 110:9354–9361

    Article  CAS  Google Scholar 

  195. Driessen-Hölscher B (1998) Adv Catal 42:473–505

    Article  Google Scholar 

  196. Horvath I, Rabai J (1994) Science 266:72–75

    Article  CAS  Google Scholar 

  197. Suarez PAZ, Dullius JEL, Einloft S et al (1996) Polyhedron 15:1217–1219

    Article  CAS  Google Scholar 

  198. Wagner M (2004) Chim Oggi 22:17–21

    CAS  Google Scholar 

  199. Floris T, Kluson P, Muldoon MJ et al (2009) Catal Lett doi:10.1007/s10562-009-0233-3

    Google Scholar 

  200. Floris T, Kluson P, unpublished results

    Google Scholar 

  201. Hashiguchi S, Fujii A, Takehara J et al (1995) J Am Chem Soc 117:7562–7563

    Article  CAS  Google Scholar 

  202. Xiaohua H, Jackie Y (2007) Chem Commun 18:1825–1827

    Google Scholar 

  203. Ying JY (2006) Chem Eng Sci 61:1540–1548

    Article  CAS  Google Scholar 

  204. Badley RD, Ford WT (1989) J Org Chem 54:5437–5443

    Article  CAS  Google Scholar 

  205. Schmidt-Winkel P, Lukens WW Jr, Zhao D et al (1999) J Am Chem Soc 121:254–255

    Article  CAS  Google Scholar 

  206. Samec JSM, Bäckvall J-E, Andersson PG et al (2006) Chem Soc Rev 35:237–248

    Article  CAS  Google Scholar 

  207. Noyori R, Hashiguchi S (1997) Acc Chem Res 30:97–102

    Article  CAS  Google Scholar 

  208. Halpern J, Harrod JF, James BR (1966) J Am Chem Soc 88:5150–5155

    Article  CAS  Google Scholar 

  209. Basu B, Mandal B, Das S et al (2008) Beilstein J Org Chem 4:53

    Article  CAS  Google Scholar 

  210. Isaeva V, Sharf V, Nifant’ev N et al (1998) Stud Surf Sci 118:237–243

    CAS  Google Scholar 

  211. Parambadath S, Singh AP (2009) Catal Today 141:161–167

    Article  CAS  Google Scholar 

  212. Zhao D, Feng J, Huo Q et al (1998) Science 279:548–552

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Authors wish to express their thanks to the Czech – Hungarian bilateral project Mobility Contact “Advanced Catalytic Reactions for Fine Chemicals” No. MEB 040802.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Agnes Zsigmond .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer Netherlands

About this chapter

Cite this chapter

Zsigmond, A., Notheisz, F., Kluson, P., Floris, T. (2010). Chemoselective and Enantioselective Hydrogenations on Immobilized Complexes. 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_9

Download citation

Publish with us

Policies and ethics