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

doi:10.6023/cjoc201303033

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (9): 2004-2009.DOI: 10.6023/cjoc201303033 Previous Articles Next Articles

Notes

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

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 发布日期:2013-05-09
通讯作者: 马宁 E-mail:mntju@tju.edu.cn
基金资助:
国家自然科学基金(No. 20802049)资助项目

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

Xu Liang, Yang Anwei, Ma Ning

Department of Chemistry, School of Science, Tianjin University, Tianjin 300072

Received:2013-03-22 Revised:2013-05-03 Published:2013-05-09
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20802049)

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]. Chin. J. Org. Chem., 2013, 33(9): 2004-2009.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

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.

氧化石墨催化醇和酚的四氢吡喃化保护与脱保护

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

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jie Liu, Feng Han, Shuangyan Li, Tianyu Chen, Jianhui Chen, Qing Xu. Transition Metal-Free Selective Aerobic Olefination of Methyl N-Heteroarenes with Alcohols [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 573-583.
[2]	Hong'en Tong, Hongyu Guo, Rong Zhou. Progress on Visible-Light Promoted Addition Reactions of Inert C—H Bonds to Carbonyls [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 54-69.
[3]	Jianghu Dong, Liangming Xuan, Chi Wang, Chenxi Zhao, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 111-136.
[4]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[5]	Hongqiong Zhao, Miao Yu, Dongxue Song, Qi Jia, Yingjie Liu, Yubin Ji, Ying Xu. Progress on Decarboxylation and Hydroxylation of Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 70-84.
[6]	Boyu Yan, Jieliang Wu, Jinfei Deng, Dan Chen, Xiushen Ye, Qiuli Yao. Recent Progress in Light-Driven Direct Dehydroxylation and Derivation of Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3055-3066.
[7]	Lu Liu, Shuguang Zhang, Renwei Hu, Xiaoxiao Zhao, Jingnan Cui, Weitao Gong. Synthesis and Properties of Phenolic Resin Polymers Based on Pillar[5]arene [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2808-2814.
[8]	Suzhen Zhang, Wenwen Zhang, Hui Yang, Qing Gu, Shuli You. Rhodium-Catalyzed Enantioselective Spiroannulation of 2-Alkenylphenols with Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2926-2933.
[9]	Xiaoyu Zhang, Xinyan Li, Bing Cui, Zhihui Shao, Mingqin Zhao. Design, Synthesis and Antioxidant Activity of Tetrahydro-β-carbolines [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2885-2894.
[10]	Xinqiang Chen, Jing Zhang. Progress in the Study of Dehydroxymethylation of Primary Alcohol [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2711-2719.
[11]	Yanhua Gao, Yinpan Zhang, Yan Zhang, Tao Song, Yong Yang. Visible-Light-Induced Aerobic Oxidation of Alcohols over Surface Oxygen Vacancies-Enriched Nb₂O₅ [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2572-2579.
[12]	Xiaojing Hu, Feixiang Guo, Runqing Zhu, Bingqi Zhou, Tao Zhang, Lizhen Fang. Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2239-2244.
[13]	Kai Lu, Haoqi Qu, Xi Chen, Hui Qiu, Jing Zheng, Mengtao Ma. Catalyst-Free and Solvent-Free Hydroboration of Alkynes and Alkenes with Catecholborane [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2197-2205.
[14]	Baichuan Mo, Chunxia Chen, Jinsong Peng. Research Progress in Application of Lignin and Its Derivatives Supported Metal Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1215-1240.
[15]	Haiqing Wang, Shuang Yang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 974-999.