Skip to main content
SpringerLink
Log in

Hydroformylation in Aqueous Biphasic Media Assisted by Molecular Receptors

  • Chapter
  • First Online:
Hydroformylation for Organic Synthesis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 342))

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 229.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 299.99
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

Abbreviations

3-α-1:

2,3-Dimethyl-6-(3-sulfonato-n-propyl)-α-cyclodextrin potassium salt

3-β-1:

2,3-Dimethyl-6-(3-sulfonato-n-propyl)-β-cyclodextrin potassium salt

4-α-1:

2,3-Dimethyl-6-(3-sulfonato-n-butyl)-α-cyclodextrin potassium salt

4-β-1:

2,3-Dimethyl-6-(3-sulfonato-n-butyl)-β-cyclodextrin potassium salt

4-β-2:

2,3-Diethyl-6-(3-sulfonato-n-propyl)-β-cyclodextrin potassium salt

acac:

Acetylacetonate

AC-β-CD:

2,6-Diacetyl-β-cyclodextrin

BiphTS:

Tris(p-sulfonatobiphenyl)phosphine trisodium salt

CRYSME-β-CD:

Randomly methylated-β-cyclodextrin (substitution degree = 5)

DIME-α-CD:

2,6-Dimethyl-α-cyclodextrin

DIME-β-CD:

2,6-Dimethyl-β-cyclodextrin

h:

Hour(s)

HP-α-CD:

Hydroxypropyl-α-cyclodextrin

HP-β-CD:

Hydroxypropyl-β-cyclodextrin

HTMAP-α-CD:

O-(2-Hydroxy-3-trimethylammonio-n-propyl)-α-cyclodextrin chloride

HTMAP-β-CD:

O-(2-Hydroxy-3-trimethylammonio-n-propyl)-β-cyclodextrin chloride

L:

Liter(s)

Me:

Methyl

min:

Minute(s)

mol:

Mole(s)

MTMAP/ME-α-CD:

O-(2-Methoxy-3-trimethylammonio-n-propyl)-α-cyclodextrin

Ph:

Phenyl

polyNAS:

Poly(N-acryloyloxysuccinimide)

RAME-α-CD:

Randomly methylated α-cyclodextrin (substitution degree = 10.8)

RAME-β-CD:

Randomly methylated-β-cyclodextrin (substitution degree = 12.6)

RASBE/ME-β-CD:

Randomly methylsulfobutylether-β-cyclodextrin

RASBE-β-CD:

Randomly sulfobutylated-β-CD

SBE-β-CD:

Sulfobutylether-β-cyclodextrin

SULFA-β-CD:

Sulfated-β-cyclodextrin

t-Bu:

tert-Butyl

TPPMS:

m-Monosulfonatophenyldiphenylphosphine sodium salt

TPPTS:

Tris(m-sulfonatophenyl)phosphine trisodium salt

TRIME-β-CD:

2,3,6-Trimethyl-β-cyclodextrin

α-CD:

α-Cyclodextrin

α-D-GluP:

α-d-Glucopyranose

β-CD:

β-Cyclodextrin

γ-CD:

γ-Cyclodextrin

References

  1. Anastas PT, Warner JC (1998) Green chemistry theory and practice. Oxford University Press, New York

    Google Scholar 

  2. van Leeuwen PWNM, Claver C (2000) Rhodium catalyzed hydroformylation. Kluwer, Dordrecht

    Google Scholar 

  3. Kohlpaintner CW, Fischer RW, Cornils B (2001) Appl Catal A 221:219–225

    Article  CAS  Google Scholar 

  4. Bahrmann H, Bogdanovic S, van Leeuwen PWNM (2004) In: Cornils B, Herrmann WA (eds) Aqueous-phase organometallic catalysis. Wiley-VCH, Weinheim, pp 391–409

    Google Scholar 

  5. Liu S, Xiao J (2007) J Mol Catal A Chem 270:1–43

    Article  CAS  Google Scholar 

  6. Wachsen O, Himmler K, Cornils B (1998) Catal Today 42:373–379

    Article  CAS  Google Scholar 

  7. Kalck P, Dessoudeix M (1999) Coord Chem Rev 192:1185–1198

    Article  Google Scholar 

  8. Purwanto P, Delmas H (1995) Catal Today 24:135–140

    Article  CAS  Google Scholar 

  9. Gimenez-Pedros M, Aghmiz A, Claver C, Masdeu-Bultó AM, Sinou D (2003) J Mol Catal A Chem 200:157–163

    Article  CAS  Google Scholar 

  10. Li M, Li YZ, Chen H, He YE, Li XJ (2003) J Mol Catal A Chem 194:13–17

    Article  CAS  Google Scholar 

  11. Riisager A, Hanson BE (2002) J Mol Catal A Chem 189:195–202

    Article  CAS  Google Scholar 

  12. Wang L, Chen H, He Y, Li Y, Li M, Li X (2003) Appl Catal A 242:85–88

    Article  CAS  Google Scholar 

  13. Yang C, Bi X, Mao Z (2002) J Mol Catal A Chem 187:35–46

    Article  CAS  Google Scholar 

  14. Barros HJV, Hanson BE, Gusevskaya EV, Dos Santos EN (2004) Applied Catal A 278:57–63

    Article  CAS  Google Scholar 

  15. Fu H, Li M, Chen H, Li X (2006) J Mol Catal A Chem 259:156–160

    Article  CAS  Google Scholar 

  16. Desset SL, Cole-Hamilton DJ, Foster DF (2007) Chem Commun 1933–1935

    Google Scholar 

  17. Miyagawa CC, Kupka J, Schumpe A (2005) J Mol Catal A Chem 234:9–17

    Article  CAS  Google Scholar 

  18. Peng Q, Yang Y, Wang C, Liao X, Yuan Y (2003) Catal Lett 88:219–225

    Article  CAS  Google Scholar 

  19. Ding H, Hanson BE, Bartik T, Bartik B (1994) Organometallics 13:3761–3763

    Article  CAS  Google Scholar 

  20. Hanson BE, Ding H, Kohlpaintner CW (1998) Catal Today 42:421–429

    Article  CAS  Google Scholar 

  21. Goedheijt MS, Hanson BE, Reek JNH, Kamer PCJ, van Leeuwen PWNM (2000) J Am Chem Soc 122:1650–1657

    Article  CAS  Google Scholar 

  22. Bortenschlager M, Schöllhorn N, Wittmann A, Weberskirch R (2007) Chemistry 13:520–528

    Article  CAS  Google Scholar 

  23. Kunna K, Müller C, Loos J, Vogt D (2006) Angew Chem Int Ed 45:7289–7292

    Article  CAS  Google Scholar 

  24. Monflier E, Fremy G, Castanet Y, Mortreux A (1995) Angew Chem Int Ed 34:2269–2271

    Article  CAS  Google Scholar 

  25. Szejtli J (1998) Chem Rev 98:1743–1753

    Article  CAS  Google Scholar 

  26. Hedges AR (1998) Chem Rev 98:2035–2044

    Article  CAS  Google Scholar 

  27. Monflier E, Komiyama M (2006) In: Dodziuk H (ed) Cyclodextrins and their complexes: chemistry, analytical methods, applications. Wiley-VCH, Weinheim, pp 93–105

    Google Scholar 

  28. Lee JT, Alper H (1990) Tetrahedron Lett 31:4101–4104

    Article  CAS  Google Scholar 

  29. Zahalka HA, Januszkiewicz K, Alper H (1986) J Mol Catal 35:249–253

    Article  CAS  Google Scholar 

  30. Harada A, Hu Y, Takahashi S (1986) Chem Lett 2083–2084

    Google Scholar 

  31. Karakhanov EA, Filippova TY, Martynova SA, Maximov AL, Predeina VV, Topchieva IN (1998) Catal Today 44:189–198

    Article  CAS  Google Scholar 

  32. Lee JT, Alper H (1990) Tetrahedron Lett 31:1941–1942

    Article  CAS  Google Scholar 

  33. Pinel C, Gendreau-Diaz N, Bréhéret A, Lemaire M (1996) J Mol Catal A Chem 112:L157–L161

    Article  CAS  Google Scholar 

  34. Lee JT, Alper H (1990) J Org Chem 55:1854–1856

    Article  CAS  Google Scholar 

  35. Zahalka H, Alper H (1986) Organometallics 5:1909–1911

    Article  CAS  Google Scholar 

  36. Benyei A, Joo F (1990) J Mol Catal 58:151–163

    Article  CAS  Google Scholar 

  37. Anderson JR, Campi EM, Jackson WR (1991) Catal Lett 9:55–58

    Article  CAS  Google Scholar 

  38. Monflier E, Blouet E, Barbaux Y, Mortreux A (1994) Angew Chem Int Ed Engl 33:2100–2102

    Article  Google Scholar 

  39. Monflier E, Tilloy S, Bertoux F, Castanet Y, Mortreux A (1997) New J Chem 21:857–859

    CAS  Google Scholar 

  40. Lacroix T, Bricout H, Tilloy S, Monflier E (1999) Eur J Org Chem 3127–3129

    Google Scholar 

  41. Tilloy S, Bricout H, Monflier E (2002) Green Chem 4:188–193

    Article  CAS  Google Scholar 

  42. Torque C, Bricout H, Hapiot F, Monflier E (2004) Tetrahedron 60:6487–6493

    Article  CAS  Google Scholar 

  43. Hapiot F, Lyskawa J, Bricout H, Tilloy S, Monflier E (2004) Adv Synth Catal 346:83–89

    Article  CAS  Google Scholar 

  44. Blach P, Landy D, Fourmentin S, Surpateanu G, Bricout H, Ponchel A, Hapiot F, Monflier E (2005) Adv Synth Catal 347:1301–1307

    Article  CAS  Google Scholar 

  45. Takeo K, Mitoh H, Uemura K (1989) Carbohydr Res 187:203–221

    Article  CAS  Google Scholar 

  46. Kenichi Y, Atsushi M, Yukio T, Mitsukatsu S, Yoshiaki Y, Tomoyuki I (1996) JP Patent 8,333,406

    Google Scholar 

  47. Deratani A, Lelièvre G, Maraldo T, Sébille B (1989) Carbohydr Res 192:215–222

    Article  CAS  Google Scholar 

  48. Sueur B, Leclercq L, Sauthier M, Castanet Y, Mortreux A, Bricout H, Tilloy S, Monflier E (2005) Chemistry 11:6228–6236

    Article  CAS  Google Scholar 

  49. Kirschner D, Jaramillo M, Green T, Hapiot F, Leclercq L, Bricout H, Monflier E (2008) J Mol Catal A 286:11–20

    Article  CAS  Google Scholar 

  50. Blach P (2005) PhD thesis, University of Littoral Côte d'Opale, France

    Google Scholar 

  51. Tilloy S, Bertoux F, Mortreux A, Monflier E (1999) Catal Today 48:245–253

    Article  CAS  Google Scholar 

  52. Monflier E, Tilloy S, Fremy G, Castanet Y, Mortreux A (1995) Tetrahedron Lett 36:9481–9484

    Article  CAS  Google Scholar 

  53. Dessoudeix M, Urrutigoïty M, Kalck P (2001) Eur J Inorg Chem 1797–1800

    Google Scholar 

  54. Mathivet T, Méliet C, Castanet Y, Mortreux A, Caron L, Tilloy S, Monflier E (2001) J Mol Catal A Chem 176:105–116

    Article  CAS  Google Scholar 

  55. Ferreira M, Legrand FX, Machut C, Bricout H, Tilloy S, Monflier M (2012) Dalton Trans 41:8643–8647

    Article  CAS  Google Scholar 

  56. Dabbawala AA, Parmar JN, Jasra RV, Bajaj HC, Monflier E (2009) Catal Commun 10:1808–1812

    Article  CAS  Google Scholar 

  57. Potier J, Menuel S, Fournier D, Fourmentin S, Woisel P, Monflier E, Hapiot F (2012) ACS Catal 2:1417–1420

    Article  CAS  Google Scholar 

  58. Fourmentin S, Outirite M, Blach P, Landy D, Ponchel A, Monflier E, Surpateanu G (2007) J Hazard Mater 141:92–97

    Article  CAS  Google Scholar 

  59. Sieffert N, Wipff G (2007) Chemistry 13:1978–1990

    Article  CAS  Google Scholar 

  60. Sieffert N, Wipff G (2006) J Phys Chem B 110:4125–4134

    Article  CAS  Google Scholar 

  61. Leclercq L, Bricout H, Tilloy S, Monflier E (2007) J Colloid Interface Sci 307:481–487

    Article  CAS  Google Scholar 

  62. Kirschner D, Green T, Hapiot F, Tilloy S, Leclercq L, Bricout H, Monflier E (2006) Adv Synth Catal 348:379–386

    Article  CAS  Google Scholar 

  63. Monflier E, Tilloy S, Méliet C, Mortreux A, Landy D, Fourmentin S, Surpateanou G (1999) New J Chem 23:469–472

    Article  CAS  Google Scholar 

  64. Caron L, Tilloy S, Monflier E, Wieruszeski JM, Lippens G, Landy D, Fourmentin S, Surpateanu G (2000) J Incl Phenom 38:361–379

    Article  CAS  Google Scholar 

  65. Da Costa A, Monflier E, Landy D, Fourmentin S, Surpateanou G (2001) Surf Sci 470:275–283

    Article  Google Scholar 

  66. Hapiot F, Leclercq L, Azaroual N, Fourmentin S, Tilloy S, Monflier E (2008) Curr Org Synth 5:162–172

    Article  CAS  Google Scholar 

  67. Leclercq L, Sauthier M, Castanet Y, Mortreux A, Bricout H, Monflier E (2005) Adv Synth Catal 347:55–59

    Article  CAS  Google Scholar 

  68. Monflier E, Bricout H, Hapiot F, Tilloy S, Aghmiz A, Masdeu-Bultó AM (2004) Adv Synth Catal 346:425–431

    Article  CAS  Google Scholar 

  69. Reetz MT (1997) Top Catal 4:187–200

    Article  Google Scholar 

  70. Reetz MT, Waldvogel SR (1997) Angew Chem Int Ed Engl 36:865–867

    Article  CAS  Google Scholar 

  71. Reetz MT (1998) Catal Today 42:399–411

    Article  CAS  Google Scholar 

  72. Reetz MT (1998) J Heterocycl Chem 35:1065–1073

    Article  CAS  Google Scholar 

  73. Armspach D, Matt D (1999) Chem Commun 1073–1074

    Google Scholar 

  74. Machut-Binkowski C, Legrand FX, Azaroual N, Tilloy S, Monflier E (2010) Chemistry 16:10195–10201

    Article  CAS  Google Scholar 

  75. Legrand FX, Six N, Slomianny C, Bricout H, Tilloy S, Monflier E (2011) Adv Synth Catal 353:1325–1334

    Article  CAS  Google Scholar 

  76. Tran DN, Legrand FX, Menuel S, Bricout H, Tilloy S, Monflier E (2012) Chem Commun 48:753–755

    Article  CAS  Google Scholar 

  77. Tilloy S, Crowyn G, Monflier E, van Leeuwen PWNM, Reek JNH (2006) New J Chem 30:377–383

    Article  CAS  Google Scholar 

  78. Hapiot F, Tilloy S, Monflier E (2006) Chem Rev 106:767–781

    Article  CAS  Google Scholar 

  79. Leclercq L, Hapiot F, Tilloy S, Ramkisoensing K, Reek JNH, van Leeuwen PWNM, Monflier E (2005) Organometallics 24:2070–2075

    Article  CAS  Google Scholar 

  80. Dabbawala AA, Bajaj HC, Bricout H, Monflier E (2012) Appl Catal A Gen 413–414:273–279

    Article  Google Scholar 

  81. Legrand FX, Hapiot F, Tilloy S, Guerriero A, Peruzzini M, Gonsalvi L, Monflier E (2009) Appl Catal A Gen 362:62–66

    Article  CAS  Google Scholar 

  82. Tilloy S, Genin E, Hapiot F, Landy D, Fourmentin S, Genêt JP, Michelet V, Monflier E (2006) Adv Synth Catal 348:1547–1552

    Article  CAS  Google Scholar 

  83. Ding H, Hanson BE, Glass TE (1995) Inorg Chim Acta 229:329–333

    Article  CAS  Google Scholar 

  84. Six N, Guerriero A, Landy D, Peruzzini M, Gonsalvi L, Hapiot F, Monflier E (2011) Catal Sci Technol 1:1347–1353

    Article  CAS  Google Scholar 

  85. Ferreira M, Bricout H, Azaroual N, Landy D, Tilloy S, Hapiot F, Monflier E (2012) Adv Synth Catal 354:1337–1346

    Article  CAS  Google Scholar 

  86. Gutsche CD (2008) Calixarenes: an introduction. RSC, Cambridge

    Google Scholar 

  87. Homden DM, Redshaw C (2008) Chem Rev 108:5086–5130

    Article  CAS  Google Scholar 

  88. Li ZY, Chen JW, Liu Y, Xia W, Wang L (2011) Curr Org Chem 15:39–61

    Article  CAS  Google Scholar 

  89. Shimizu S, Shirakawa S, Suzuki T (2001) Tetrahedron 57:6169–6173

    Article  CAS  Google Scholar 

  90. Karakhanov EE, Maksimov AL, Runova EA, Kardasheva YS, Terenina MV, Buchneva TS, Gushkova AY (2003) Macromol Symp 204:159–173

    Article  CAS  Google Scholar 

  91. Monnereau L, Sémeril D, Matt D, Toupet L (2009) Adv Synth Catal 351:1629–1636

    Article  CAS  Google Scholar 

  92. Cobley CJ, Pringle PG (2011) Catal Sci Technol 1:239–242

    Article  CAS  Google Scholar 

  93. Shimizu S, Sasaki Y, Hirai C (2000) Angew Chem Int Ed 39:1256–1259

    Article  CAS  Google Scholar 

  94. Shirakawa S, Shimizu S, Sasaki Y (2001) New J Chem 25:777–779

    Article  CAS  Google Scholar 

  95. Machut C, Patrigeon J, Tilloy S, Bricout H, Hapiot F, Monflier E (2007) Angew Chem Int Ed 46:3040–3042

    Article  CAS  Google Scholar 

  96. Patrigeon J, Hapiot F, Canipelle M, Menuel S, Monflier E (2010) Organometallics 29:6668–6674

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Unité de Catalyse et de Chimie du Solide, CNRS UMR 8181, Faculté des Sciences Jean Perrin, Eric Monflier, Université d’Artois, SP18, 62307, Lens Cedex, France

    Frédéric Hapiot, Hervé Bricout, Sébastien Tilloy & Eric Monflier

Authors
  1. Frédéric Hapiot
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hervé Bricout
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sébastien Tilloy
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Eric Monflier
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Eric Monflier .

Editor information

Editors and Affiliations

  1. Dipartimento Farmaco Chimico Tecnologico, University of Siena, Siena, Italy

    Maurizio Taddei

  2. Laboratoire d'Innovation Thérapeutique, CNRS-Université de STRASBOURG, Illkirch, France

    André Mann

Rights and permissions

Reprints and permissions

Copyright information

© 2013 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Hapiot, F., Bricout, H., Tilloy, S., Monflier, E. (2013). Hydroformylation in Aqueous Biphasic Media Assisted by Molecular Receptors. In: Taddei, M., Mann, A. (eds) Hydroformylation for Organic Synthesis. Topics in Current Chemistry, vol 342. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2013_431

Download citation

Publish with us

Policies and ethics

Search

Navigation