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| Graphite oxide-catalyzed acetylation of alcohols and phenols |
| Yuan-Yuan Liua, Jun-Mei Qia, Li-Sha Baia, Yue-Long Xua, Ning Mab, Fei-Fei Suna,b |
a Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China;
b Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin 300072, China |
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Abstract Graphite oxide (GO) was used as a catalyst for the reactions of alcohols and phenols with acetic anhydride. The acetates of primary and secondary alcohols were prepared in good to excellent yields in short reaction time under mild conditions. Electron deficient phenols could be converted to the corresponding acetates steadily. As an efficient catalyst, GO is easily available, cheap, moderately toxic and weakly acidic.
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Received: 17 July 2015
Published: 11 January 2016
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Corresponding Authors:
Ning Ma, Fei-Fei Sun
E-mail: mntju@tju.edu.cn;sff@tju.edu.cn
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| [1] |
P.G.M. Wuts, T.W. Greene, Greene's Protective Groups in Organic Synthesis, fourth ed., John Wiley and Sons, New Jersey, 2007.
|
| [2] |
J. Otera, J. Nishikido, Esterification:Methods Reactions and Applications, second ed., WILEY-VCH Verlag GmbH & Co, Weinheim, 2010.
|
| [3] |
N.G. Khaligh, Poly(N-vinylimidazole) as an efficient catalyst for acetylation of alcohols, phenols, thiols and amines under solvent-free conditions, RSC Adv. 3(2013) 99-110.
|
| [4] |
A. Khazaei, A. Rostami, F.Mantashlo, p-Toluenesulfonyl chloride as a new and effective catalyst for acetylation and formylation of hydroxyl compounds under mild conditions, Chin. Chem. Lett. 21(2010) 1430-1434.
|
| [5] |
F. Shirini, A.R. Sakhaei, M. Abedini, V(HSO4)3 catalyzed chemoselectivity acetylation of alcohols and phenols in solution and under solvent-free conditions, Chin. Chem. Lett. 20(2009) 439-443.
|
| [6] |
F. Rajabi, A heterogeneous cobalt(Ⅱ) Salen complex as an efficient and reusable catalyst for acetylation of alcohols and phenols, Tetrahedron Lett. 50(2009) 395-397.
|
| [7] |
D. Chen, H.B. Feng, J.H. Li, Graphene oxide:preparation, functionalization, and electrochemical applications, Chem. Rev. 112(2012) 6027-6053.
|
| [8] |
D.R. Dreyer, S. Park, C.W. Bielawski, R.S. Ruoff, The chemistry of graphene oxide, Chem. Soc. Rev. 39(2010) 228-240.
|
| [9] |
D.R. Dreyer, A.D. Todd, C.W. Bielawski, Harnessing the chemistry of graphene oxide, Chem. Soc. Rev. 43(2014) 5288-5301.
|
| [10] |
C.K. Chua, M. Pumera, Carbocatalysis:the state of "metal-free" catalysis, Chem. Eur. J. 21(2015) 12550-12562.
|
| [11] |
S. Navalon, A. Dhakshinamoorthy, M. Alvaro, H. Garcia, Carbocatalysis by graphene-based materials, Chem. Rev. 114(2014) 6179-6212.
|
| [12] |
D.R. Dreyer, H.P. Jia, C.W. Bielawski, Graphene oxide:a convenient carbocatalyst for facilitating oxidation and hydration reactions, Angew. Chem. Int. Ed. 49(2010) 6813-6816.
|
| [13] |
D.R. Dreyer, H.P. Jia, A.D. Todd, J.X. Geng, C.W. Bielawski, Graphite oxide:a selective and highly efficient oxidant of thiols and sulfides, Org. Biomol. Chem. 9(2011) 7292-7295.
|
| [14] |
S. Kumari, A. Shekhar, H.P. Mungse, O.P. Khatri, D.D. Pathak, Metal-free one-pot synthesis of amides using graphene oxide as an efficient catalyst, RSC Adv. 4(2014) 41690-41695.
|
| [15] |
A. Dhakshinamoorthy, M. Alvaro, P. Concepción, V. Forné s, H. Garcia, Graphene oxide as an acid catalyst for the room temperature ring opening of epoxides, Chem. Commun. 48(2012) 5443-5445.
|
| [16] |
H.L. Wang, T.S. Deng, Y.X. Wang, et al., Graphene oxide as a facile acid catalyst for the one-pot conversion of carbohydrates into 5-ethoxymethylfurfural, Green Chem. 15(2013) 2379-2383.
|
| [17] |
X.Q. Gao, S.H. Zhu, Y.W. Li, Graphene oxide as a facile solid acid catalyst for the production of bioadditives from glycerol esterification, Catal. Commun. 62(2015) 48-51.
|
| [18] |
S. Verma, H.P. Mungse, N. Kumar, et al., Graphene oxide:an efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes, Chem. Commun. 47(2011) 12673-12675.
|
| [19] |
S. Khodabakhshi, B. Karami, K. Eskandari, S. Jafar Hoseinia, A. Rashidib, Graphene oxide nanosheets promoted regioselective and green synthesis of new dicoumarols, RSC Adv. 4(2014) 17891-17895.
|
| [20] |
C.L. Su, R. Tandiana, J. Balapanuru, et al., Tandem catalysis of amines using porous graphene oxide, J. Am. Chem. Soc. 137(2015) 685-690.
|
| [21] |
J.M. Qi, Y.L. Xu, N. Ma, F.F. Sun, Graphite oxide-catalyzed esterification and transesterification, Chin. J. Org. Chem. 33(2013) 1839-1846.
|
| [22] |
L. Xu, A.W. Yang, N. Ma, Graphite oxide as an efficient and reusable catalyst for tetrahydropyranylation/depyranylation of alcohols and phenols, Chin. J. Org. Chem. 33(2013) 2004-2009.
|
| [23] |
Y.L. Xu, J.M. Qi, F.F. Sun, N. Ma, Carbocatalysis:reduced graphene oxide-catalyzed Boc protection of hydroxyls and graphite oxide-catalyzed deprotection, Tetrahedron Lett. 56(2015) 2744-2748.
|
| [24] |
W.S. Hummers Jr., R.E. Offeman, Preparation of graphitic oxide, J. Am. Chem. Soc. 80(1958) 1339.
|
| [25] |
A.M. Dimiev, L.B. Alemany, J.M. Tour, Graphene oxide Origin of acidity, its instability in water, and a new dynamic structural model, ACS Nano 7(2013) 576-588.
|
|
|
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