Advances in the Application of Urea-Hydrogen Peroxide to Oxidation Reactions

doi:10.6023/cjoc1103243

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (02): 254-265 .DOI: 10.6023/cjoc1103243 Previous Articles Next Articles

Reviews

过氧化脲在氧化反应中的应用研究进展

计立^a, 刘金强^b, 钱超^a, 陈新志^a

a 浙江大学化学工程与生物工程学系杭州 310027;
b 洛阳师范学院化学化工学院洛阳 471022

收稿日期:2011-03-24 修回日期:2011-05-03 发布日期:2012-03-09
通讯作者: 钱超 E-mail:supmoney@163.com
基金资助:
浙江省重点科技创新团队(No. 2009R50002)和中央高校基本科研业务费专项资金(No. 2011QNA4018)资助项目.

Advances in the Application of Urea-Hydrogen Peroxide to Oxidation Reactions

Ji Li^a, Liu Jinqiang^b, Qian Chao^a, Chen Xinzhi^a

a Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027;
b College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022

Received:2011-03-24 Revised:2011-05-03 Published:2012-03-09
Supported by:
Project supported by the Aid Program for Key Science and Technology Innovative Research Team in Zhejiang Province (No. 2009R50002) and the Fundamental Research Funds for the Central Universities of China (No. 2011QNA4018).

Oxidation reactions play important roles in organic synthesis, where hydrogen peroxide and peroxy acids are always employed as oxidants. Urea-hydrogen peroxide (UHP) is recently utilized in numerous oxidation reactions as environment- friendly solidified hydrogen peroxide, due to its advantages such as stable at room temperature, high hydrogen peroxide content (36.2%) and the potential for releasing it in a controlled manner. Several applications of UHP to organic synthesis are summarized according to reaction type, especially for epoxidation, Baeyer-Villiger oxidation, N-oxidation, oxidation of sulfides to sulfoxides and sulfones, oxidative-halogenation and so on.

Key words: urea-hydrogen peroxide (UHP), epoxidation, Baeyer-Villiger oxidation, N-oxidation, sulfones, sulfoxides, oxidative-halogenation

Cite this article

Ji Li, Liu Jinqiang, Qian Chao, Chen Xinzhi. Advances in the Application of Urea-Hydrogen Peroxide to Oxidation Reactions[J]. Chin. J. Org. Chem., 2012, 32(02): 254-265 .

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Jones, C. W. Applications of Hydrogen Peroxide and Derivatives, Royal Society of Chemistry, Cambridge, 1999, p. 79.

[2] Lane, B. S.; Burgess, K. Chem. Rev. 2003, 103(7), 2457.

[3] Sato, K.; Aoki, M.; Noyori, R. Science 1998, 281(5383), 1646.

[4] Baxendale, J. H.; Wilson, J. A. Trans. Faraday Soc. 1957, 53, 344.

[5] Mckillop, A.; Sanderson, W. R. Tetrahedron 1995, 51(22), 6145.

[6] Muzart, J. Synthesis 1995, 1325.

[7] McKillop, A.; Sanderson, W. R. J. Chem. Soc., Perkin Trans. 1 2000, (4), 471.

[8] Cooper, M. S.; Heaney, H.; Newbold, A. J.; Sanderson, W. R. Synlett 1990, (9), 533.

[9] Armarego, W. L. F.; Chai, C. L. L. Purification of Laboratory Chemicals, 6th ed., Elsevier, Oxford, 2009, p. 470.

[10] Gonsalves, A. M. D. R.; Johnstone, R. A. W.; Pereira, M. M.; Shaw, J. J. Chem. Res., Synop. 1991, (8), 208.

[11] Smith, M. B.; March, J. Advanced Organic Chemistry: Reactions Mechanisms Structure, John Wiley & Sons, New Jersey, 2007, p. 1169.

[12] Adam, W.; Mitchell, C. M. Angew. Chem., Int. Ed. 1996, 35(5), 533.

[13] Boehlow, T. R.; Spilling, C. D. Tetrahedron Lett. 1996, 37(16), 2717.

[14] Malhotra, R.; Kumar, S.; Satyam, A. J. Chem. Soc., Chem. Commun. 1994, (11), 1339.

[15] Balch, A. L.; Costa, D. A.; Noll, B. C.; Olmstead, M. M. J. Am. Chem. Soc. 1995, 117(35), 8926.

[16] Murray, R. W.; Iyanar, K. Tetrahedron Lett. 1997, 38(3), 335.

[17] Legros, J.; Crousse, B.; Bonnet-Delpon, D.; Begue, J. P. Eur. J. Org. Chem. 2002, (19), 3290.

[18] Fan, C. L.; Lee, W. D.; Teng, N. W.; Sun, Y. C.; Chen, K. M. J. Org. Chem. 2003, 68(25), 9816.

[19] Valderrama, J. A.; Gonzalez, M. F.; Torres, C. Heterocycles 2003, 60(10), 2343.

[20] Ankudey, E. G.; Olivo, H. F.; Peeples, T. L. Green Chem. 2006, 8(10), 923.

[21] Jin, H.; Zhao, H. Y.; Zhao, F. H.; Li, S. H.; Liu, W.; Zhou, G. P.; Tao, K.; Hou, T. P. Ultrason. Sonochem. 2009, 16(3), 304.

[22] Mahmoodi, N. O.; Yazdanbakhsh, M. R.; Ghanbari, F. Synth. Commun. 2010, 40(21), 3181.

[23] Bouh, A. O.; Espenson, J. H. J. Mol. Catal. A: Chem. 2003, 200(1～2), 43.

[24] Ichihara, J.; Iteya, K.; Kambara, A.; Sasaki, Y. Catal. Today 2003, 87(1～4), 163.

[25] Saladino, R.; Bernini, R.; Neri, V.; Crestini, C. Appl. Catal. A 2009, 360(2), 171.

[26] Carreiro, E. D.; Burke, A. J.; Curto, M. J. M.; Teixeira, A. J. J. Mol. Catal. A: Chem. 2004, 217(1～2), 69.

[27] Kureshy, R. I.; Khan, N. U. H.; Abdi, S. H. R.; Singh, S.; Ahmed, I.; Shukla, R. S.; Jasra, R. V. J. Catal. 2003, 219(1), 1.

[28] Carreiro, E. D.; Yong-En, G.; Burke, A. J. J. Mol. Catal. A: Chem. 2005, 235(1～2), 285.

[29] Egami, H.; Katsuki, T. Angew. Chem., Int. Ed. 2008, 47(28), 5171.

[30] Egami, H.; Oguma, T.; Katsuki, T. J. Am. Chem. Soc. 2010, 132(16), 5886.

[31] Maity, N. C.; Abdi, S. H. R.; Kureshy, R. I.; Khan, N. U. H.; Suresh, E.; Dangi, G. P.; Bajaj, H. C. J. Catal. 2011, 277(1), 123.

[32] Marigo, M.; Bachmann, S.; Halland, N.; Braunton, A.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43(41), 5507.

[33] Rios, M. Y.; Salazar, E.; Olivo, H. F. Green Chem. 2007, 9(5), 459.

[34] Marcos, I. S.; Beneitez, A.; Castaneda, L.; Moro, R. F.; Basabe, P.; Diez, D.; Urones, J. G. Synlett 2007, (10), 1589.

[35] Garrido, N. M.; Garcia, M.; Sanchez, M. R.; Diez, D.; Urones, J. G. Synlett 2010, (3), 387.

[36] Gunaratne, H. Q. N.; McKervey, M. A.; Feutren, S.; Finlay, J.; Boyd, J. Tetrahedron Lett., 1998, 39(31), 5655.

[37] Balicki, R. J. Prakt. Chem., 1999, 341(2), 184.

[38] Balicki, R. Synth. Commun. 1999, 29(13), 2235.

[39] Varma, R. S.; Naicker, K. P. Org. Lett. 1999, 1(2), 189.

[40] Sasaki, Y.; Ushimaru, K.; Iteya, K.; Nakayama, H.; Yamaguchi, S.; Ichihara, J. Tetrahedron Lett. 2004, 45(52), 9513.

[41] Hasaninejad, A.; Chehardoli, G.; Zolfigol, M. A.; Abdoli, A. Phosphorus, Sulfur Silicon Relat. Elem. 2011, 186(2), 271.

[42] Saito, B.; Katsuki, T. Tetrahedron Lett. 2001, 42(23), 3873.

[43] Miyazaki, T.; Katsuki, T. Synlett 2003, (7), 1046.

[44] Bernier, D.; Wefelscheid, U. K.; Woodward, S. Org. Prep. Proced. Int. 2009, 41(3), 173.

[45] Kaczmarek, L.; Balicki, R.; Nantkanamirski, P. Chem. Ber. 1992, 125(8), 1965.

[46] Caron, S.; Do, N. M.; Sieser, J. E. Tetrahedron Lett. 2000, 41(14), 2299.

[47] Balicki, R.; Golinski, J. Synth. Commun. 2000, 30(8), 1529.

[48] Rong, D. W.; Phillips, V. A.; Rubio, R. S.; Castro, M. A.; Wheelhouse, R. T. Tetrahedron Lett., 2008, 49(48), 6933.

[49] Marcantoni, E.; Petrini, M.; Polimanti, O. Tetrahedron Lett. 1995, 36(20), 3561.

[50] Goti, A.; Nannelli, L. Tetrahedron Lett. 1996, 37(33), 6025.

[51] Murray, R. W.; Iyanar, K.; Chen, J. X.; Wearing, J. T. J. Org. Chem. 1996, 61(23), 8099.

[52] Soldaini, G.; Cardona, F.; Goti, A. Org. Lett. 2007, 9(3), 473.

[53] Cardona, F.; Bonanni, M.; Soldaini, G.; Goti, A. ChemSusChem 2008, 1(4), 327.

[54] Singh, B.; Jain, S. L.; Khatri, P. K.; Sain, B. Green Chem. 2009, 11(12), 1941.

[55] Podgoršek, A.; Zupan, M.; Iskra, J. Angew. Chem., Int. Ed. 2009, 48(45), 8424.

[56] Roche, D.; Prasad, K.; Repic, O.; Blacklock, T. J. Tetrahedron Lett. 2000, 41(13), 2083.

[57] Kabalka, G. W.; Yang, K. Synth. Commun. 1998, 28(20), 3807.

[58] Paul, S.; Nanda, P.; Gupta, R. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2005, 44(1), 184.

[59] Lee, J. C.; Park, H. J. Synth. Commun. 2006, 36(6), 777.

[60] Lee, J. C.; Park, H. J. Synth. Commun. 2007, 37(1-3), 87.

[61] El-Ahl, A. A. S.; Elbeheery, A. H.; Amer, F. A. Synth. Commun. 2011, 41(10), 1508.

[62] Sosnowski, M.; Skulski, L. Molecules 2002, 7(12), 867.

[63] Pavlinac, J.; Zupan, M.; Stavber, S. Org. Biomol. Chem. 2007, 5(4), 699.

[64] Pavlinac, J.; Zupan, M.; Stavber, S. Acta Chim. Slov. 2008, 55(4), 841.

[65] Lulinski, P.; Kryska, A.; Sosnowski, M.; Skulski, L. Synthesis 2004, (3), 441.

[66] Balicki, R.; Kaczmarek, L. Synth. Commun. 1993, 23(22), 3149.

[67] Balicki, R. Synth. Commun. 2001, 31(14), 2195.

[68] Heaney, H.; Newbold, A. J. Tetrahedron Lett. 2001, 42(37), 6607.

[69] Park, H. J.; Lee, J. C. Synlett 2009, (1), 79.

[70] Ballini, R.; Marcantoni, E.; Petrini, M. Tetrahedron Lett. 1992, 33(33), 4835.

[71] Cardona, F.; Soldaini, G.; Goti, A. Synlett 2004, (9), 1553.

[72] Finlay, J.; McKervey, M. A.; Gunaratne, H. Q. N. Tetrahedron Lett. 1998, 39(31), 5651.

[73] Filipan-Litvic, M.; Litvic, M.; Vinkovic, V. Tetrahedron 2008, 64(24), 5649.

[74] Suto, Y.; Yamagiwa, N.; Torisawa, Y. Tetrahedron Lett. 2008, 49(40), 5732.

过氧化脲在氧化反应中的应用研究进展

Advances in the Application of Urea-Hydrogen Peroxide to Oxidation Reactions

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Duoduo Xiao, Jiantao Zhang, Peng Zhou, Weibing Liu. Metal-Free α-C(sp³)—H Methylenation of Aryl Ketones to Form γ-Keto Sulfoxides with Dimethyl Sulfoxide [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3900-3906.
[2]	Biao Han, Yaoyao Zhang, Shuhan Chen, Mengge Zhao, Nan Li, Weishuang Li, Lei Zhu. Preparation of Axially Grafted Temperature-Responsive Chiral Salen Mn^III and Application in Asymmetric Epoxidation of Olefins in Water [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 244-253.
[3]	Yi Zhou, Zhuojun Li, Minghui Hu, Zhaohua Yan, Sen Lin. Oxidation of Sulfides with SO₂F₂/H₂O₂/Base [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1545-1550.
[4]	Weiwei Wang, Yu Zhao, Xinlei Liu, Jiazhen Jiang, Ming'an Wang. Synthesis and Antifungal Activity of 3-Aryl-7-methyl- 7-hydroxy-2-octen-6-olide [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2343-2353.
[5]	Hongbo Dong, Weiwei Wang, Yu Zhao, Xinlei Liu, Ming'an Wang. Synthesis and Antifungal Activity of 3,7-Dimethyl-7-hydroxy-2-octen-6-olide Analogues [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1646-1657.
[6]	Li Liu, Hong Xiao, Fuhong Xiao, Yanjun Xie, Huawen Huang, Guojun Deng. Synthesis of β-Ketosulfone from Sodium Sulfinate and Aryl Ethyl Ketone/Indanone [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4749-4757.
[7]	Na Meng, Qishun Liu, Ruisheng Liu, Yufen Lü, Xiaohui Zhao, Wei Wei. Recent Advances in Arylations and Sulfonylations of Arylazo Sulfones [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4639-4650.
[8]	Gucheng Yuan, Jiawei Liu, Shihang Yu, Chaonan Yuan, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of (3Z,6Z,9S,10R)-9,10-Epoxy-3,6-heneicosadiene, Sex Pheromone Component of Hyphantria cunea [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4437-4443.
[9]	Jiang Xiaoying, Yao Chuansheng, Tong Chuo, Bai Renren, Zhou Tao, Xie Yuanyuan. Selective Oxidation of Sulfides/Disulfides to Sulfoxides/ Thiosulfonates Using t-Butyl Hydroperoxide (TBHP) without Catalyst [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1752-1759.
[10]	Qi Lianshan, Wang Tao, Wei Yongmei, Tian Hengshui. Study on the Effect of Co-reductant Aldehydes on Epoxidation of Propylene Catalyzed by Metalloporphyrins [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1305-1309.
[11]	Chen Demao, Sun Yuanyuan, Dong Daoqing, Han Qingqing, Wang Zuli. Visible-Light Induced Sulfonylation of Nitroolefins for the Synthesis of Vinyl Sulfones under Photocatalyst Free Conditions [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4267-4273.
[12]	Zheng He, Zhou Yuke, Lin Xianfu, Wu Qi. Recent Developments in Protein Engineering and Catalytic Oxidations of Baeyer-Villiger Monooxygenase [J]. Chin. J. Org. Chem., 2019, 39(4): 903-915.
[13]	Tao Xuefen, Sheng Rong, Bao Kun, Wang Yuxin, Jin Yinxiu. Progress of Difluoromethyl Heteroaryl Sulfones as Difluoroalkylation Reagents [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2726-2734.
[14]	Sun Moran, Dai Lei, Yang Hua, Liu Hongmin, Yu Dequan. Enantioselective Synthesis of Core Structures of Hydramicromelins A, B and C [J]. Chin. J. Org. Chem., 2018, 38(9): 2443-2449.
[15]	Chen Zhen, Guo Kang, Chen Rongshun, Gu Chen, Zhou Huating, Zhu Yingguang. Facile Access to β-Ketosulfones via Mn-Mediated Reductive Coupling of α-Bromoketones with Sulfonyl Chlorides [J]. Chin. J. Org. Chem., 2018, 38(4): 963-968.