SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 9: 2004 - 2009

DOI: https://doi.org/10.6023/cjoc201303033

Notes

Graphite Oxide as an Efficient and Reusable Catalyst for Tetrahydropyranylation/Depyranylation of Alcohols and Phenols

  • Xu Liang ,
  • Yang Anwei ,
  • Ma Ning
Expand
  • Department of Chemistry, School of Science, Tianjin University, Tianjin 300072

Received date: 2013-03-22

  Revised date: 2013-05-03

  Online published: 2013-05-09

Supported by

Project supported by the National Natural Science Foundation of China (No. 20802049)

Fold

Abstract

Graphite oxide serves as an efficient, lowly toxic, easily available, weakly acidic and reusable catalyst for tetrahydropyranyl protection and deprotection of alcohols and phenols. Various alcohols and phenols, including the unsaturated ones, were steadily tetrahydropyranylated and subsequently depyranylated into the corresponding products at room temperature during short reaction time in good to quantitative yields. Graphite oxide could be reused at least four times. This method is convenient, safe, economical and environmentally benign.

Key words： graphite oxide; catalyst; tetrahydropyranylation; alcohol; phenol

Cite this article

Xu Liang , Yang Anwei , Ma Ning . Graphite Oxide as an Efficient and Reusable Catalyst for Tetrahydropyranylation/Depyranylation of Alcohols and Phenols[J]. Chinese Journal of Organic Chemistry, 2013 , 33(9) : 2004 -2009 . DOI: 10.6023/cjoc201303033

References

[1] Wuts, P. G. M.; Greene, T. W. Greene’s Protective Groups in Organic Synthesis, 4th ed., John Wiley and Sons, New Jersey, 2007, p. 24.
[2] Bartoli, G.; Giovannini, R.; Giuliani, A.; Marcantoni, E.; Massaccesi, M.; Melchiorre, P.; Paoletti, M.; Sambri, L. Eur. J. Org. Chem. 2006, 1476.
[3] Rahmatpour, A. Polyhedron 2012, 44, 66.
[4] Wang R.; Sun, M.-Z.; Jiang, H. Res. Chem. Intermed. 2011, 37, 61.
[5] Stephens, J. R.; Butler, P. L.; Clow, C. H.; Oswald, M. C.; Smith, R. C.; Mohan, R. S. Eur. J. Org. Chem. 2003, 3827.
[6] Varala, R.; Adapa, S. R. Can. J. Chem. 2006, 84, 1174.
[7] Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Mohammadpoor-Baltork, I.; Gharaati, S. Inorg. Chim. Acta 2010, 363, 1523.
[8] Gharib, A.; Jahangia, M. J. Serb. Chem. Soc. 2012, 77, 287.
[9] Reddy, T. S.; Ravinder, K.; Suryakiran, N.; Narasimhulu, M.; Mahesh, K. C.; Venkateswarlu, Y. Tetrahedron Lett. 2006, 47, 2341.
[10] Hajipour, A. R.; Kargosha, M.; Ruoho, A. E. Synth. Commun. 2009, 39, 1084.
[11] Yang, J. H.; Zhang, X.; Liu, W. Y. Chin. Chem. Lett. 2008, 19, 893.
[12] Wang, M.; Song, Z.-G.; Jiang, H.; Gong, H. Chin. J. Org. Chem. 2008, 28, 1629 (in Chinese).
(王敏, 宋志国, 姜恒, 宫红, 有机化学, 2008, 28, 1629.)
[13] Wang, Y.-G.; Wu, X.-X.; Jiang, Z.-Y. Tetrahedron Lett. 2004, 45, 2973.
[14] Chen, D.; Feng, H.; Li, J. Chem. Rev. 2012, 112, 6027.
[15] Dreyer, D. R.; Jia, H. P.; Bielawski, C. W. Angew. Chem., Int. Ed. 2010, 49, 6813.
[16] Huang, H.; Huang, J.; Liu, Y.-M.; He, H.-Y.; Cao, Y.; Fan, K.-N. Green Chem. 2012, 14, 930.
[17] Verma, S.; Mungse, H. P.; Kumar, N.; Choudhary, S.; Jain, S. L. Chem. Commun. 2011, 47, 12673.
[18] Dhakshinamoorthy, A.; Alvaro, M.; Concepción, P.; Fornés, V.; Garcia, H. Chem. Commun. 2012, 48, 5443.
[19] Zhang, X.; Xu, L.; Wang, X.; Ma, N.; Sun, F. Chin. J. Chem. 2012, 30, 1525.
[20] Qi, J. M.; Xu, Y. L.; Ma, N.; Sun, F. F. Chin. J. Org. Chem. 2013, 33, 1839 (in Chinese).
(齐俊梅, 许跃龙, 马宁, 孙菲菲, 有机化学, 2013, 33, 1839.)
[21] Marcano, D. C.; Kosynkin, D. V.; Berlin, J. M.; Sinitskii, A.; Sun, Z.; Slesarev, Z.; Alemany, L. B.; Lu, W.; Tour, J. M. ACS Nano 2010, 4, 4806.
[22] Park, S.; An, J.; Potts, J. R.; Velamakanni, A.; Murali, S.; Ruoff, R. S. Carbon 2011, 49, 3019.
[23] Szabó, T.; Tombácz, E.; Illés, E.; Dékány, I. Carbon 2006, 44, 537.
[24] Narender, N.; Reddy, K. S. K.; Kumar, M. A.; Rohitha, C. N.; Kulkarni, S. J. Catal. Lett. 2010, 134, 175.
[25] Khan, A. T.; Mondal, E.; Borah, B. M.; Ghosh, S. Eur. J. Org. Chem. 2003, 4113.
[26] Khan, A. T.; Ghosh, S.; Choudhury, L. H. Eur. J. Org. Chem. 2005, 4891.
[27] Hon, Y.-S.; Lee, C.-F.; Chen, R.-J.; Szu, P.-H. Tetrahedron 2001, 57, 5991.
[28] Hajipour, A. R.; Nasresfahani, Z. Synth. Commun. 2012, 42, 1995.
[29] Ouedraogo, A.; Lessard, J. Can. J. Chem. 1991, 69, 474.
[30] Molander, G. A.; Calvacanti, L. N. J. Org. Chem. 2011, 76, 623.
Options
Outlines

/

〈 〉