SIOC English
有机化学
高级检索

有机化学 >

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

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

研究简报

氧化石墨催化醇和酚的四氢吡喃化保护与脱保护

  • 徐亮 ,
  • 杨安卫 ,
  • 马宁
展开
  • 天津大学理学院化学系 天津 300072

收稿日期: 2013-03-22

  修回日期: 2013-05-03

  网络出版日期: 2013-05-09

基金资助

国家自然科学基金(No. 20802049)资助项目

收起

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

摘要

氧化石墨作为一种高效、低毒、易得、可重复使用的弱酸性催化剂用于醇和酚的四氢吡喃化保护与脱保护反应. 反应在室温下短时间内即可完成, 产物收率高, 分子中的碳碳不饱和键不受影响, 氧化石墨可重复使用至少4次. 该方法具有操作简便、安全、经济、环境友好等优点.

关键词： 氧化石墨; 催化剂; 四氢吡喃化; 醇; 酚

本文引用格式

徐亮 , 杨安卫 , 马宁 . 氧化石墨催化醇和酚的四氢吡喃化保护与脱保护[J]. 有机化学, 2013 , 33(9) : 2004 -2009 . DOI: 10.6023/cjoc201303033

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

参考文献

[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
文章导航

/

〈 〉