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Improved aqueous Cannizzaro reaction in presence of cyclodextrin

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Abstract

An aqueous hydroxypropyl-β-cyclodextrin solution has been used to increase the conversion of 4-biphenylcarboxaldehyde into the corresponding alcoholic and carboxylic substrates, by means of a Cannizzaro reaction. The observed enhancement has been ascribed to a partial solubilization of 4-biphenylcarboxaldehyde. In addition, as the main part of the organic substrates still remains insoluble, synthesized products are easily recovered by filtration. As a consequence, the basic cyclodextrin solution might also be reused for a new synthetic cycle, without significant loss of conversion. Aqueous solid–liquid biphasic reaction in presence of cyclodextrins thus seems to be a promising tool in the green chemistry field.

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Abbreviations

HPBCD:

Hydroxypropyl-β-cyclodextrin

References

  1. Szejtli, J.: Chemistry, physical and biological properties of cyclodextrins. Compr. Supramol. Chem. 3, 5–40 (1996)

    CAS  Google Scholar 

  2. Del Valle, E.M.M.: Cylodextrins and their uses: a review. Process Biochem. 39(9), 1033–1046 (2004)

    Article  CAS  Google Scholar 

  3. Uekama, K., Hirayama, F., Irie, T.: Cyclodextrin drug carrier systems. Chem. Rev. 98(5), 2045–2076 (1998)

    Article  CAS  Google Scholar 

  4. Dabbawala, A.A., Parmar, J.N., Jasra, R.V., Bajaj, H.C., Monflier, E.: Cobalt catalyzed hydroformylation of higher olefins in the presence of chemically modified cyclodextrins. Catal. Commun. 10(14), 1808–1812 (2009)

    Article  CAS  Google Scholar 

  5. Hapiot, F., Leclercq, L., Azaroual, N., Fourmentin, S., Tilloy, S., Monflier, E.: Rhodium-catalyzed hydroformylation promoted by modified cyclodextrins: current scope and future developments. Curr. Org. Synth. 5(2), 162–172 (2008)

    Article  CAS  Google Scholar 

  6. Bhosale, S.V., Bhosale, S.V.: β-Cyclodextrin as a catalyst in organic synthesis. Mini Rev. Org. Chem. 4(3), 231–242 (2007)

    Article  CAS  Google Scholar 

  7. Kunishima, M., Watanabe, Y., Terao, K., Tani, S.: Substrate-specific amidation of carboxylic acids in a liquid–liquid two-phase system using cyclodextrins as inverse phase-transfer catalysts. Eur. J. Org. Chem. 22, 4535–4540 (2004)

    Article  Google Scholar 

  8. Tilloy, S., Bricout, H., Monflier, E.: Cyclodextrins as inverse phase transfer catalysts for the biphasic catalytic hydrogenation of aldehydes: a green and easy alternative to conventional mass transfer promoters. Green Chem. 4(3), 188–193 (2002)

    Article  CAS  Google Scholar 

  9. Kalck, P., Miquel, L., Dessoudeix, M.: Various approaches to transfers improvement during biphasic catalytic hydroformylation of heavy alkenes. Catal. Today 42(4), 431–440 (1998)

    Article  CAS  Google Scholar 

  10. Bowden, K., El-Kaissi, F.A., Ranson, R.J.: Intramolecular catalysis. Part 5. The intramolecular Cannizzaro reaction of o-phthalaldehyde and [α, α′-2H2]-o-phthalaldehyde. J. Chem. Soc., Perkin Trans. 2 12, 2089–2092 (1990)

    Article  Google Scholar 

  11. Basavaiah, D., Sharada, D.S., Veerendhar, A.: Organo-base mediated Cannizzaro reaction. Tetrahedron Lett. 47(32), 5771–5774 (2006)

    Article  CAS  Google Scholar 

  12. Yang, X., Guo, J., Zou, G.: Lanthanide-catalysed cross-Cannizzaro reduction of aromatic aldehydes with formaldehyde. Lett. Org. Chem. 2(2), 145–147 (2005)

    Article  CAS  Google Scholar 

  13. Bikbaeva, G.G., Kislina, I.S., Vinnik, M.I.: Kinetics of the cross Cannizzaro reaction of anisic aldehyde with formaldehyde in aqueous solutions of KOH. Bull. Acad. Sci. USSR CH+ 23(12), 2616–2620 (1975)

    Article  Google Scholar 

  14. Abbaszadeh, M.R., Bowden, K.: Intramolecular catalysis. Part 4. The intramolecular Cannizzaro reaction of biphenyl-2,2-dicarbaldehyde, [α,α’-2H2]biphenyl-2,2′-dicarbaldehyde and 4,4′-or 5,5′- or 6,6′-disubstituted biphenyl-2,2′-dicarbaldehydes. J. Chem. Soc. Perkin Trans. 12(2), 2081–2087 (1990)

    Google Scholar 

  15. Bowden, K., Butt, A.M., Streater, M.: Intramolecular catalysis. Part 8. The intramolecular Cannizzaro reaction of naphthalene-1,8-dicarbaldehyde and [αα′-2H2]naphthalene-1,8-dicarbaldehyde. J. Chem. Soc., Perkin Trans. 2 4, 567–571 (1992)

    Article  Google Scholar 

  16. Morooka, S., Wakai, C., Matubayasi, N., Nakahara, M.: Noncatalytic Cannizzaro-type reaction of acetaldehyde in supercritical water. Chem. Lett. 32, 310–311 (2003)

    Article  Google Scholar 

  17. Sharifi, A., Mojtahedi, M.M., Saidi, M.R.: Microwave irradiation techniques for the Cannizzaro reaction. Tetrahedron Lett. 40(6), 1179–1180 (1999)

    Article  CAS  Google Scholar 

  18. Mohamadi, F., Richards, N.G.J., Guida, W.C., Liskamp, R., Lipton, M., Caufield, C., Chang, G., Hendrickson, T., Still, W.C.: MacroModel—an integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J. Comput. Chem. 11, 440–467 (1990)

    Article  CAS  Google Scholar 

  19. Cheng, A., Best, S.A., Merz Jr, K.M., Reynolds, C.H.: GB/SA water model for the Merck molecular force field (MMFF). J. Mol. Graph. Model. 18(3), 273–282 (2000)

    Article  CAS  Google Scholar 

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Acknowledgement

Authors wish to thank IRENI for financial support.

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Authors and Affiliations

  1. Univ Lille Nord de France, 59000, Lille, France

    M. Canipelle, D. Landy & S. Fourmentin

  2. ULCO, LSOE, 59140, Dunkerque, France

    M. Canipelle, D. Landy & S. Fourmentin

Authors
  1. M. Canipelle
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  2. D. Landy
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  3. S. Fourmentin
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Correspondence to D. Landy.

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Canipelle, M., Landy, D. & Fourmentin, S. Improved aqueous Cannizzaro reaction in presence of cyclodextrin. J Incl Phenom Macrocycl Chem 69, 349–353 (2011). https://doi.org/10.1007/s10847-010-9747-y

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  • DOI: https://doi.org/10.1007/s10847-010-9747-y

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