Chinese Journal of Organic Chemistry >
Synthesis of Phenols under Mild Conditions in Water Using Recyclable Chitosan@Copper as Catalyst
Received date: 2015-10-23
Revised date: 2015-11-16
Online published: 2015-12-10
Supported by
Project supported by the National Natural Science Foundation of China (No. 21402103), the Scientific Research Foundation of Shandong Province Outstanding Young Scientist Award (No. BS2013YY024), and the Postdoctoral Science Foundationof China (No. 150030).
A green and efficient protocol for the synthesis of phenols using recyclable chitosan@copper as catalyst was developed. Phenols can be obtained in moderate to excellent yields. The catalyst can be recycled and reused for five times without significant loss of its catalytic activity.
Key words： chitosan@copper; recyclable; phenylboronic acid; water
Zhao Suyan , Wang Zuli . Synthesis of Phenols under Mild Conditions in Water Using Recyclable Chitosan@Copper as Catalyst[J]. Chinese Journal of Organic Chemistry, 2016 , 36(4) : 862 -866 . DOI: 10.6023/cjoc201510027
[1] Rappoport, Z. The Chemistry of Phenols, Wiley-VCH, Weinheim,Germany, 2003.
[2] Zhang, R. X.; Zhang, X. D. Chemical Industry 2008, 26, 47 (in Chinese). (张日新, 张晓东, 化学工业, 2008, 26, 47.)
[3] (a) Anderson, K. W.; Ikawa, T. R.; Tundel, E. S.; Buchwald, L. J. Am. Chem. Soc.2006, 128, 10694.
(b) Willis, M. C. Angew. Chem., Int. Ed. 2007, 46, 3402.
(c) Sergeev, A. G.; Schulz, T.; Torborg, C.; Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 7595.
(d) Schulz, T.; Torborg, C.; Schäffner, B.; Huang, J.; Zapf, A.; Kadyrov, R.; Börner, A.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 918.
(e) Gallon, B. J.; Kojima, R. W.; Kaner, R. B.; Diaconescu, P. L. Angew. Chem., Int. Ed. 2007, 46, 7251.
(f) Chen, G. S.; Chan, A. S. C.; Kwong, F. Y. Tetrahedron Lett. 2007, 48, 473.
[4] (a) Yang, D. S.; Fu, H. Chem. Eur. J. 2010, 16, 2366.
(b) Kormos, C. M.; Leadbeater, N. E. Tetrahedron 2006, 62, 4728;
(c) Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725.
(d) Zhao, D. B.; Wu, N. J.; Zhang, S.; Xi, P.; Su, X. Y.; Lan, J. B.; You, J. S. Angew. Chem., Int. Ed. 2009, 48, 8729.
[5] Yin, L.; Leibescher, J. Chem. Rev. 2007, 107, 133.
[6] Li, B.; Li, M.; Yao, C. H.; Shi, Y. F.; Ye, D. R.; Wu, J.; Zhao, D. Y. J. Mater. Chem. 2013, 1, 6742.
[7] For selected examples, see: (a) Kantam, M. L.; Yadav, Y.; Laha, Y.; Srinivas, P.; Sreedhar, B.; Figueras, F. J. Org. Chem. 2009, 74, 4608.
(b) Kundu, D.; Chatterjee, T.; Ranu, B. C. Adv. Synth. Catal. 2013, 355, 2285.
(c) Brahmachari, G.; Laskar, S.; Barik, P. RSC Adv. 2013, 3, 142;
(d) Parella, R.; Kumar, A; Babu, S. A. Tetrahedron Lett. 2013, 54, 1738.
(e) Yang, S.; Wu, C.; Zhou, H.; Yang, Y.; Zhao, Y.; Wang, C.; Yang, W.; Xu, J. Adv. Synth. Catal. 2013, 355, 53.
(f) Swapna, K.; Murthy, S. N.; Jyothi, M. T.; Nageswar, Y. V. D. Org. Biomol. Chem. 2011, 5989.
(g) Hudson, R.; Ishikawa, S.; Li, C.-J.; Moores, A. Synlett 2013, 1637.
(h) Dandia, A.; Jain, A. K.; Sharma, S. RSC Adv. 2013, 3, 2924.
(i) Kumar, A. S.; Reddy, M.; M.Knorn, A.; Reiser, O.; Sreedhar, B. Eur. J. Org. Chem. 2013, 4, 674.
(j) Wang, Z. L. RSC Adv. 2015, 5, 5563.
[8] Zhang, J.; Han, D.; Zhang, H.; Chaker, M.; Zhao, Y.; Ma, D. Chem. Commun. 2012, 48, 11510.
[9] (a) Makhubela, B. C. E.; Jardine, A.; Smith, G. S. Appl. Catal. 2011, 393, 231.
(b) Lasri, J.; Leod, T. C. O. M.; Pombeiro, A. J. L. Appl. Catal. 2011, 393, 94.
(c) Yi, S. S.; Lee, D. H.; Sin, E.; Lee, Y. S. Tetrahedron Lett. 2007, 48, 6771.
[10] (a) Shen, C.; Xu, J.; Yu, W.; Zhang, P. Green Chem. 2014, 16, 3007.
(b) Shen, C.; Xu, J.; Yu, W. B.; Zhang, P. F. Green Chem. 2014, 16, 3007.
[11] Yang, B.; Mao, Z. X.; Zhu, X. H.; Wan, Y. Q. Catal. Commun. 2015, 60, 92.
[12] Pal, M.; Parasuraman, K.; Yeleswarapu, K. R. Org. Lett. 2003, 5, 349.
[13] Molander, G. A.; Cavalcanti, L. N. J. Org. Chem. 2011, 76, 623.
[14] Jiang, M.; Yang, H. J.; Li, Y.; Jia, Z. Y.; Fu, H. Chin. Chem. Lett. 2014, 25, 715.
[15] Yang, D. S.; An, B. J.; Wei, W.; Jiang, M.; You, J. M.; Wang, H. Tetrahedron 2014, 70, 3630.
[16] Xu, J. M.; Wang, X. Y.; Shao, C. W.; Su, D. Y.; Cheng, G. L.; Hu, Y. F. Org. Lett. 2010, 12, 164.
[17] Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725.
/
| 〈 |
|
〉 |
