10.1186/2228-5326-3-3

Sulfonic acid-functionalized ordered nanoporous Na+-montmorillonite as an efficient, eco-benign, and water-tolerant nanoreactor for chemoselective oxathioacetalization of aldehydes

  1. Department of Chemistry, Faculty of Science, University of Guilan, Rasht, 0098, IR
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Published in Issue 2013-01-16

How to Cite

Shirini, F., Atghia, S. V., & Mamaghani, M. (2013). Sulfonic acid-functionalized ordered nanoporous Na+-montmorillonite as an efficient, eco-benign, and water-tolerant nanoreactor for chemoselective oxathioacetalization of aldehydes. International Nano Letters, 3(1 (December 2013). https://doi.org/10.1186/2228-5326-3-3

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Abstract

Abstract Sulfonic acid-functionalized ordered nanoporous sodium montmorillonite has been found to be a mild and efficient solid acid catalyst for the chemoselective protection of a variety of carbonyl compounds as oxathiolanes in good to excellent yields. The present method offers several advantages such as short reaction times, high yields, simple procedure and mild conditions. Also, the catalyst could be recycled and reused at least for five times without noticeably decreasing the catalytic activity.

Keywords

  • Nanoreactor,
  • Oxathioacetalization,
  • SANM,
  • Na+-montmorillonite,
  • Solid acid catalyst

References

  1. Greene and Wuts (1999) Wiley https://doi.org/10.1002/0471220574
  2. Lynch and Eliel (1984) Asymmetric syntheses based on 1,3-oxathianes. 2. Synthesis of chiral tertiary alpha-hydroxy aldehydes, alpha-hydroxy acids, glycols [R1R2C(OH)CH2OH], and carbinols [R1R2C(OH)Me] in high enantiomeric purity (pp. 2943-2948) https://doi.org/10.1021/ja00322a034
  3. Utimoto et al. (1990) Highly diastereoselective reactions of ytterbium-mediated alkynyllithium and alkynylmagnesium reagents with chiral 2-acyl-1,3-oxathianes: reversal of diastereoselectivity (pp. 8189-8190) https://doi.org/10.1021/ja00178a066
  4. De (2005) K: Ruthenium(III) chloride-catalyzed thioacetalization of carbonyl compounds: scope, selectivity, and limitations (pp. 673-676) https://doi.org/10.1002/adsc.200404323
  5. Fuji et al. (1985) Chemistry of carbanions stabilized by sulfur. 1. Chemistry of 1,3-oxathianes. Synthesis and conformation of 2-substituted 1,3-oxathianes (pp. 657-661) https://doi.org/10.1021/jo00205a020
  6. Fuji et al. (1983) 2-Lithio-2-trimethylsilyl-1,3-oxathian: a possible acyl dianion equivalent (pp. 49-50) https://doi.org/10.1039/c39830000049
  7. Karimi and Seradj (2000) Zirconium tetrachloride (ZrCl4) as an efficient and chemoselective catalyst for conversion of carbonyl compounds to 1,3-oxathiolanes 2000(6) (pp. 805-806) https://doi.org/10.1055/s-2000-6692
  8. Karimi and Ma’mani (2003) Scandium(III) triflate as an efficient and recyclable catalyst for chemo-selective conversion of carbonyl compounds to 1,3-oxathiolanes (pp. 2503-2506) https://doi.org/10.1055/s-2003-42436
  9. Kazahaya et al. (2002) Indium trifluoromethanesulfonate as a mild and chemoselective catalyst for the conversion of carbonyl compounds into 1,3-oxathiolanes 2002(9) (pp. 1535-1537) https://doi.org/10.1055/s-2002-33541
  10. Yadav et al. (2001) LiBF4 catalyzed chemoselective conversion of aldehydes to 1,3-oxathiolanes and 1, 3-dithianes 2001(2) (pp. 238-239)
  11. Adibi and Jafari (2007) Facile protection of carbonyl compounds as oxathiolanes and transoxathioacetalization of oxyacetals promoted by iron(III) trifluoroacetate or trifluoromethanesulfonate as chemoselective and recyclable catalysts (pp. 679-682) https://doi.org/10.1016/j.jfluchem.2007.04.002
  12. Wilson et al. (1968) Facile synthesis of 1,3-oxathiolanes from ketones and 2-mercaptoethanol (pp. 2133-2134) https://doi.org/10.1021/jo01269a103
  13. Yadav and Fallis (1988) Cyclopentane synthesis and annulation: intramolecular radical cyclization of acetals (pp. 897-900) https://doi.org/10.1016/S0040-4039(00)82476-4
  14. Rana et al. (2003) A mild and efficient method for the protection of carbonyl compounds as oxathiolanes, dithiolanes and dithianes catalyzed by molybdenyl acetylacetonate (pp. 8597-8599) https://doi.org/10.1016/j.tetlet.2003.09.146
  15. Garlaschelli and Vidari (1990) Anhydrous lanthanum trichloride, a mild and convenient reagent for thioacetalization (pp. 5815-5816) https://doi.org/10.1016/S0040-4039(00)97967-X
  16. Bao et al. (2010) Efficient procedure for oxathioacetalization using the novel ionic liquid (pp. 2119-2122) https://doi.org/10.1002/cjoc.201090351
  17. Yadav et al. (2003) Eco-friendly and highly chemoselective 1,3-oxathio- and 1,3-dithioacetalization of aldehydes using ionic liquids (pp. 672-673) https://doi.org/10.1246/cl.2003.672
  18. Kamal et al. (2002) Oxathioacetalization, thioacetalization and transthioacetalization of carbonyl compounds by N-bromosuccinimide: selectivity and scope (pp. 6947-6951) https://doi.org/10.1016/S0040-4039(02)01610-6
  19. Mondal et al. (2002) A useful and convenient synthetic protocol for interconversion of carbonyl compounds to the corresponding 1,3-oxathiolanes and vice versa employing organic ammonium tribromide (OATB) (pp. 2843-2846) https://doi.org/10.1016/S0040-4039(02)00345-3
  20. Liang et al. (2008) Highly efficient procedure for the oxathioacetalization of carbonyl compounds under solvent-free conditions (pp. 156-159) https://doi.org/10.1016/j.catcom.2008.08.008
  21. Firouzabadi et al. (2006) Tungstophosphoric acid supported on silica gel (H3PW12O40/SiO2) as an eco-friendly, reusable and heterogeneous catalyst for chemoselective oxathioacetalization of carbonyl compounds in solution or under solvent-free conditions (pp. 14-18) https://doi.org/10.1016/j.molcata.2005.10.018
  22. Gogoi et al. (2004) Montmorillonite K-10 clay as an efficient solid catalyst for chemoselective protection of carbonyl compounds as oxathiolanes with 2-mercaptoethanol 2004(9) (pp. 1592-1594)
  23. Ballini et al. (2001) Amberlyst® 15 as a mild, chemoselective and reusable heterogeneous catalyst for the conversion of carbonyl compounds to 1,3-oxathiolanes 2001(12) (pp. 1826-1829) https://doi.org/10.1055/s-2001-17532
  24. Aoyama et al. (2004) Silica gel-supported polyphosphoric acid (PPA/SiO2) as an efficient and reusable catalyst for conversion of carbonyl compounds into oxathioacetals and dithioacetals 2004(13) (pp. 2307-2310) https://doi.org/10.1055/s-2004-832812
  25. Shirini and Albadi (2010) Melamine trisulfonic acid as a new, efficient and reusable catalyst for the chemoselective oxathioacetalyzation of aldehydes (pp. 1119-1120) https://doi.org/10.5012/bkcs.2010.31.5.1119
  26. Shirini et al. (2009) Silica sulfuric acid: a versatile reagent for oxathioacetalyzation of carbonyl compounds and deprotection of 1,3-oxathiolanes (pp. 1457-1460) https://doi.org/10.1016/j.cclet.2009.07.006
  27. Giannelis et al. (1999) Polymer-silica nanocomposites: model systems for confined polymers and polymer brushes (pp. 108-147)
  28. Shirini et al. (2011) Sulfonic acid-functionalized ordered nanoporous Na+-montmorillonite (SANM): a novel, efficient and recyclable catalyst for the chemoselective N-Boc protection of amines in solventless media (pp. 1088-1094) https://doi.org/10.1016/j.catcom.2011.03.030
  29. Shirini et al. (2012) A mild and efficient method for the chemoselective trimethylsilylation of alcohols and phenols and deprotection of silyl ethers using sulfonic acid-functionalized ordered nanoporous Na+-montmorillonite (pp. 67-72) https://doi.org/10.1016/j.clay.2012.01.014