European Journal of Chemistry

Glycerol-based SO3H-Carbon Catalyst: A green recyclable catalyst for the chemoselective synthesis of pentaerythritol diacetals



Main Article Content

Chandrakala Ummadisetti
Badari Narayana Prasad Rachapudi
Lakshmi Anu Prabhavathi Devi Bethala

Abstract

Glycerol-based SO3H-functionalized carbon catalyst was demonstrated as an efficient and recyclable green catalyst for the chemoselective synthesis of pentaerythritol diacetals with aromatic aldehydes in the presence of ketones in excellent yields in toluene at 80 °C. In addition, the catalyst also has the capability for the deprotection of pentaerythritol diacetals in methanol at reflux temperature. The recovered catalyst without any pre-treatment was reused for 5 cycles without any deactivation and leaching into the reaction medium under optimum conditions.


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Ummadisetti, C.; Rachapudi, B. N. P.; Bethala, L. A. P. D. Glycerol-Based SO3H-Carbon Catalyst: A Green Recyclable Catalyst for the Chemoselective Synthesis of Pentaerythritol Diacetals. Eur. J. Chem. 2014, 5, 536-540.

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References

[1]. Taylor, P. Mechanism and Synthesis, Royal Society of Chemistry, Cambridge, UK. 2002, 32.

[2]. Brown, J.; Lenhard, R. H.; Berstein, S. J. Am. Chem. Soc. 1964, 86, 2183-2187.
http://dx.doi.org/10.1021/ja01065a016

[3]. Saniger, E.; Campos, J. M.; Entrena, A.; Marchal, J. A.; Boulaiz, H.; Aranega, A.; Gallo, M. A.; Espinosa, A. Tetrahedron 2003, 59, 8017-8026.
http://dx.doi.org/10.1016/j.tet.2003.08.016

[4]. Bruns, K.; Conrad, J.; Steigel, A. Tetrahedron 1979, 35, 2523-2530.
http://dx.doi.org/10.1016/0040-4020(79)88015-1

[5]. Marrian, S. F. Chem. Rev. 1948, 43, 149-202.
http://dx.doi.org/10.1021/cr60134a004

[6]. Zhang, Z. H.; Li, T. S.; Jin, T. S.; Li, J. T. J. Chem. Res. (S). 1998, 10, 640-641.
http://dx.doi.org/10.1039/a803046d

[7]. Perner, J.; Stork, K.; Merger, F.; Oppenlaender, K. Ger. Offen, 1978, 2707875 (Chem. Abstr. 1978, 89, 181503x).

[8]. Jin, T.; Yang, M.; Wang, X.; Feng, G.; Li, T. J. Chem. Res. 2004, 3, 203-205.
http://dx.doi.org/10.3184/0308234041640654

[9]. Jermy, B. R.; Pandurangan, A. Catal. Comm. 2006, 7, 921-925.
http://dx.doi.org/10.1016/j.catcom.2006.03.021

[10]. Deng, G.; Ren, T. J. Chem. Res. 2003, 1, 24-25.
http://dx.doi.org/10.3184/030823403103172805

[11]. Jin, T. S.; Li, T. S.; Zhang, Z. H. Synth. Commun. 1999, 29, 1601-1606.
http://dx.doi.org/10.1080/00397919908086141

[12]. Jin, T. S.; Ma, Y. R.; Li, T. S. J. Chem. Res. (S). 1999, 268-269.

[13]. Wang, G.; Song, G.; Yang, T.; Yang, L.; Suo, J. J. Mol. Catal A: Chem. 2005, 233, 121-126.
http://dx.doi.org/10.1016/j.molcata.2005.02.006

[14]. Wang, Y.; Xu, Y. N.; Wang, Z. Z.; Dai, L. Y. Chin. Chem. Lett. 2010, 21, 524-528.
http://dx.doi.org/10.1016/j.cclet.2009.12.014

[15]. Jermy, B. R.; Pandurangan, A. J. Mol. Catal A: Chem. 2006, 256, 184-192.
http://dx.doi.org/10.1016/j.molcata.2006.04.045

[16]. Shaterian, H. R.; Rigi, F. Chin. J. Chem. 2012, 30, 695-698.
http://dx.doi.org/10.1002/cjoc.201280002

[17]. Shaterian, H. R.; Azizi, K.; Fahimi, N. Chem. Sci. Trans. 2012, 1(1), 85-90.
http://dx.doi.org/10.7598/cst2012.141

[18]. Hara, M.; Yoshida, T.; Takagaki, A.; Takata, T.; Kondo, J. N.; Hayash, S.; Domen, K. Angew. Chem. Int. Ed. 2004, 43, 2955-2958.
http://dx.doi.org/10.1002/anie.200453947

[19]. Toda, M.; Takagaki, A.; Okamura, M.; Kondo, J. N.; Hayashi, S.; Dome, K.; Hara, M. Nature 2005, 438, 178-178.
http://dx.doi.org/10.1038/438178a

[20]. Takagaki, A.; Toda, M.; Okamura, M.; Kondo, J. N.; Hayashi, S.; Domen, K.; Hara, M. Catal. Today 2006, 116, 157-161.
http://dx.doi.org/10.1016/j.cattod.2006.01.037

[21]. Zong, M. H.; Duan, Z. Q.; Lou, W. Y.; Smith, T. J.; Wu, H. Green Chem. 2007, 9, 434-437.
http://dx.doi.org/10.1039/b615447f

[22]. Prabhavaeti Devi, B. L. A.; Gangadhar, K. N.; Prasad, P. S. S.; Jagannadh, B.; R. B. N. Prasad, Chem. Sus. Chem. 2009, 2, 617-620.
http://dx.doi.org/10.1002/cssc.200900097

[23]. Prabhavaeti Devi, B. L. A.; Gangadhar, K. N.; Kumar, K. L. N. S.; Sanker, K. S.; Prasad, R. B. N.; Prasad, P. S. S. J. Mol. Cat. A: Chem. 2011, 345, 96-100.
http://dx.doi.org/10.1016/j.molcata.2011.05.025

[24]. Ramesh, K.; Murthy, S. N.; Karnakar, K.; Nageswar, Y. V. D.; Vijayalakhsmi, K.; Prabhavaeti Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 1126-1129.
http://dx.doi.org/10.1016/j.tetlet.2011.12.092

[25]. Karnakar, K.; Murthy, S. N.; Ramesh, K.; Nageswar, Y. V. D.; Reddy, T. V. K.; Prabhavathi Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 1968-1973.
http://dx.doi.org/10.1016/j.tetlet.2012.02.018

[26]. Ramesh, K.; Murthy, S. N.; Karnakar, K.; Reddy, K. H. V.; Nageswar, Y. V. D.; Vijay, M.; Prabhavaeti Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 2636-2638.
http://dx.doi.org/10.1016/j.tetlet.2012.03.051

[27]. Karnakar, K.; Murthy, S. N.; Ramesh, K.; Reddy, K. H. V.; Nageswar, Y. V. D.; Chandrakala, U.; Prabhavathi Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 3497-3501.
http://dx.doi.org/10.1016/j.tetlet.2012.04.122

[28]. Rao, B. M.; Reddy, G. N.; Reddy, T. V. K.; Prabhavathi Devi, B. L. A.; Prasad, R. B. N.; Yadav, J. S.; Reddy, B. V. S.; Tetrahedron Lett. 2013, 54, 2466-2471.
http://dx.doi.org/10.1016/j.tetlet.2013.02.089

[29]. Gangadhar, K. N.; Vijay, M.; Prasad, R. B. N.; Prabhavathi Devi, B. L. A. Green Sust. Chem. 2013, 3, 122-218.

[30]. Manneganti, V.; Rachapudi, B. N. P.; Bethala, L. A. P. D. Eur. J. Chem. 2014, 5(1), 167-170.
http://dx.doi.org/10.5155/eurjchem.5.1.167-170.917

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