综述与进展

过氧化氢选择性氧化硫醚的研究进展

  • 刘课艳 ,
  • 偶辉 ,
  • 石先莹 ,
  • 董雪芬 ,
  • 马文娟 ,
  • 魏俊发
展开
  • 陕西师范大学化学化工学院 陕西省大分子科学重点实验室 西安 710062

收稿日期: 2013-10-16

  修回日期: 2013-11-25

  网络出版日期: 2013-12-18

基金资助

国家自然科学基金(Nos. 21072123,21272145)、中央高校基本科研业务费专项资金(Nos. GK201102005,GK261001095)资助项目

Recent Progress in the Selective Oxidation of Sulfides withHydrogen Peroxide

  • Liu Keyan ,
  • Ou Hui ,
  • Shi Xianying ,
  • Dong Xuefen ,
  • Ma Wenjuan ,
  • Wei Junfa
Expand
  • Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062

Received date: 2013-10-16

  Revised date: 2013-11-25

  Online published: 2013-12-18

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21072123, 21272145), the Fundamental Research Funds for the Central Universities (Nos. GK201102005, GK261001095).

摘要

亚砜和砜类化合物具有广谱生物活性而有广泛的应用前景,同时作为有机合成的重要中间体广泛应用于碳-碳键形成、分子重组反应中. 硫醚直接氧化是制备亚砜和砜的主要方法之一. 在众多关于硫醚选择性氧化反应的研究中,过氧化氢作为清洁氧化剂备受关注. 鉴于此,就过氧化氢选择性氧化硫醚反应中的重要金属催化体系和一些非金属催化体系的研究状况作一综述,简要介绍各类催化氧化体系的催化效果.

本文引用格式

刘课艳 , 偶辉 , 石先莹 , 董雪芬 , 马文娟 , 魏俊发 . 过氧化氢选择性氧化硫醚的研究进展[J]. 有机化学, 2014 , 34(4) : 681 -692 . DOI: 10.6023/cjoc201310019

Abstract

Sulfoxides and sulfones have broad applications in pharmaceutical agents and pesticide due to their biologically activities and they are important synthetic intermediates in C—C bond formation and various molecular rearrangements. The selective oxidation of sulfides is a straightforward and frequently used method to obtain sulfoxides and sulfones. Among various oxidizing agents, hydrogen peroxide as benign oxidant has attracted organic chemists' attention for a long time. This review summarizes the recent and important catalytic systems of metal and nonmetal in this area. The catalytic effect of different catalytic systems is briefly discussed herein.

参考文献

[1] (a) Maurya, M. R.; Chandrakar, A. K.; Chand, S. J. Mol. Catal. A: Chem. 2007, 274, 192.(b) Nicolaou, K. C.; Magolda, R. L.; Sipio, W. J.; Barnette, W. E.; Lysenko. Z.; Joullie. M. M. J. Am. Chem. Soc. 1980, 102, 3784.(c) Kropp, P. J.; Breton, G. W.; Fields, J. D.; Tung, J. C.; Loomis, B. R. J. Am. Chem. Soc. 2000, 122, 4280.(d) Breton, G. W.; Fields, J. D.; Kropp, P. J. Tetrahedron Lett. 1995, 36, 3525.(e) Bonadies, F.; De Angelis, F.; Locati, L.; Scettri, A. Tetrahedron Lett. 1996, 37, 7129.(f) Venier, C. G.; Squires, T. G.; Chen, Y. Y.; Hussmann, G. P.; Shei, J. C.; Smith, B. F. J. Org. Chem. 1982, 47, 3774.

[2] (a) Bortolini, O.; Campestrini, S.; Di Furia, F.; Modena, G. J. Org. Chem. 1987, 52, 5093.(b) Ballistreri, F. P.; Bazzo, A.; Tomaselli, G. A.; Toscano, R. M. J. Org. Chem. 1992, 57, 7074.

[3] (a) Neumann, R.; Juwiler, D. Tetrahedron 1996, 52, 8781.(b) Gresley, N. M.; Griffith, W. P.; Laemmel, A. C.; Nogueira, H. I. S.; Parkin, B. C. J. Mol. Catal. A: Chem. 1997, 117, 185.(c) Collins, F. M.; Lucy, A. R.; Sharp, C. J. Mol. Catal. A: Chem. 1997, 117, 397.

[4] Sato, K.; Hyodo, M.; Aoki, M.; Zheng, X.-Q.; Noyori, R. Tetrahedron 2001, 57, 2469.

[5] Gharah, N.; Chakraborty, S.; Mukherjee, A.; Bhattacharyya, R. Inorg. Chim. Acta 2009, 362, 1089.

[6] Xue, X. L.; Zhao, W.; Ma, B. C.; Ding, Y. Catal. Commun. 2012, 26, 73.

[7] Das, S. P.; Boruah, J. J.; Chetry, H.; Islam, N. S. Tetrahedron Lett. 2012, 53, 1163.

[8] Koo, D. H.; Kim, M.; Chang, S. Org. Lett. 2005, 7, 5015.

[9] Karimi, B.; Ghoreishi-Nezhad, M.; Clark, J. H. Org. Lett. 2005, 7, 625.

[10] Shi, X. Y.; Ma, W. J.; Han, X. Y.; Zhang, W.; Lu, A. F.; Wei, J. F. Chem. J. Chin. Univ. 2011, 32, 2321 (in Chinese).(石先莹, 马文娟, 韩晓燕, 张文, 吕爱凤, 魏俊发, 高等学校化学学报, 2011, 32, 2321.)

[11] Shi, X. Y.; Ma, W. J.; Ou, H.; Han, X. Y.; Lu, C. M.; Chen, Y.; Wei, J. F. J. Braz. Chem. Soc. 2012, 23, 1536.

[12] Jeyakumar, K.; Chakravarthy, R. D.; Chand, D. K. Catal. Commun. 2009, 10, 1948.

[13] Tundo, P.; Romanelli, G. P.; Vazquez, P. G.; Arico, F. Catal. Commun. 2010, 11, 1181.

[14] Romanelli, G. P.; Villabrille, P. I.; Caceres, C. V.; Vazquez, P. G.; Tundo, P. Catal. Commun. 2011, 12, 726.

[15] Raghavan, P. S.; Ramaswamy, V.; Upadhya, T. T.; Sudalai, A.; Ramaswamy, A. V.; Sivasanker, S. J. Mol. Catal. A: Chem. 1997, 122, 75.

[16] Sharma, R. K.; Pandey, A.; Gulati, S. Polyhedron 2012, 45, 86.

[17] Grivani, G.; Gholampoor, N. J. Iran. Chem. Soc. 2012, 9, 349.

[18] Anisimov, A. V.; Fedorova, E. V.; Lesnugin, A. Z.; Senyavin, V. M.; Aslanov, L. A.; Rybakov, V. B.; Tarakanova, A. V. Catal. Today 2003, 78, 319.

[19] Smith, T. S.; Pecoraro, V. L. Inorg. Chem. 2002, 41, 6754.

[20] Berrocal, T.; Larrea, E. S.; Iglesias, M.; Arriortua, M. R. J. Mol. Catal. A: Chem. 2011, 335, 176.

[21] Hussain, S.; Talukdar, D. S.; Bharadwaj, K.; Chaudhur, M. K. Tetrahedron Lett. 2012, 53, 6512.

[22] Al-Hashimi, M.; Fisset, E.; Sullivan, A. C.; Wilson, J. R. H. Tetrahedron Lett. 2006, 47, 8017.

[23] Prasanth, K. L.; Maheswaran, H. J. Mol. Catal. A: Chem. 2007, 268, 45.

[24] Islam, S. M.; Roy, A. S.; Mondal, P.; Salam, N. J. Mol. Catal. A: Chem. 2012, 358, 38.

[25] Zolfigol, M. A.; Khazaei, A.; Safaiee, M.; Mokhles, M.; Rostamiana, R.; Bagheri, M.; Shiri, M.; Krugere, H. G. J. Mol. Catal. A: Chem. 2013, 370, 80.

[26] (a) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772.(b) Yuste, F.; Ortiz, B.; Carrasco, A.; Peralta, M.; Quintero, L.; Sanchez-Obregon, R.; Walls, F.; Garcia Ruano, J. L. Tetrahedron: Asymmetry 2000, 11, 3079.(c) Vetter, A. H.; Berkessel, A. Tetrahedron Lett. 1998, 39, 1741.(d) Ando, R.; Yagyu, T.; Maeda, M. Inorg. Chim. Acta 2004, 357, 2237.

[27] Jeong, Y.-C.; Choi, S.; Hwang, Y. D.; Ahn, K.-H. Tetrahedron Lett. 2004, 45, 9249.

[28] Sun, J.; Zhu, C.; Dai, Z.; Yang, M.; Pan, Y.; Hu, H. J. Org. Chem. 2004, 69, 8500.

[29] Gao, A. P.; Wang, M.; Wang, D. P.; Zhang, L.; Liu, H. B.; Tian, W.; Sun, L. C. Chin. J. Catal. 2006, 27, 743 (in Chinese).(高爱萍, 王梅, 王东平, 张路, 刘海彬, 田伟, 孙立成, 催化学报, 2006, 27, 743.)

[30] Liu, H. B.; Wang, M.; Wang, Y.; Wang, Y.; Sun, H.; Sun, L. C. Catal. Commun. 2009, 11, 294.

[31] Zeng, Q. L.; Gao, Y. X.; Dong, J. Y.; Weng, W.; Zhao, Y. F. Tetrahedron: Asymmetry 2011, 22, 717.

[32] (a) Romanowski, G.; Wera, M. Polyhedron 2013, 50, 179.(b)Romanowski, G. J. Mol. Catal. A: Chem. 2013, 368369, 137.

[33] (a) Raghavan, P. S.; Ramaswamy, V.; Upadhya, T. T.; Sudalai, A.; Ramaswamy, A. V.; Sivasanker, S. J. Mol. Catal. A: Chem. 1997, 122, 75.(b) Raju, S. V. N.; Upadhya, T. T.; Ponatnam, S.; Daniel, T.; Sudalai, A. Chem. Commun. 1996, 16, 1969.(c) Moreau, P.; Hulea, V.; Gomez, S.; Brunel, D.; Renzo, F. D. Appl. Catal. A: Gen. 1997, 155, 253.(d) Corma, A.; Iglesias, M.; Sanchez, F. Catal. Lett. 1996, 39, 153.(e) Kholdeeva, O. A.; Derevyankin, A. Y.; Shmakov, A. N.; Trukhan, N. N.; Paukshtis, E. A.; Tuel, A.; Romannikov, V. N. J. Mol. Catal. A: Chem. 2000, 158, 417.(f) Reddy, R. S.; Reddy, J. S.; Kumar, R.; Kumar, P. J. Chem. Soc. Chem. Commun. 1992, 2, 84.

[34] Pitchen, P.; Dunach, E.; Deshmukh, M. N.; Kagan, H. B. J. Am. Chem. Soc. 1984, 106, 81.

[35] Hulea, V.; Oreau, P.; Di Renzo, F. J. Mol. Catal. 1996, 111, 325.

[36] Bharadwaj, S. K.; Sharma, S. N.; Hussain, S.; Chaudhuri, M. K. Tetrahedron Lett. 2009, 50, 3767.

[37] Hulea, V.; Maciuca, A-L.; Cojocariu, A-M.; Ciocan, C-E.; Dumitriu, E. C. R. Chimie 2009, 12, 723.

[38] Rahimizadeh, M.; Rajabzadeh, G.; Khatami, S-M.; Eshghi, H.; Shiri, A. J. Mol. Catal. A: Chem. 2010, 323, 59.

[39] (a) Cojocariu, A. M.; Mutin, P. H.; Dumitriu, E.; Fajula, F.; Vioux, A.; Hulea, V. Appl. Catal. B: Environ. 2010, 97, 407.(b) Cojocariu, A. M.; Mutin, P. H.; Dumitriu, E.; Aboulaich, A.; Vioux, A.; Fajula, F.; Hulea, V. Catal. Today 2010, 157, 270.

[40] De Rosa, M.; Lamberti, M.; Pellecchia, C.; Scettri, A.; Villano, R.; Soriente, A. Tetrahedron Lett. 2006, 47, 7233.

[41] Talsi, E. P.; Bryliakov, K. P. Appl. Organomet. Chem. 2013, 27, 239.

[42] (a) Duboc-Toia, C.; Ménage, S.; Ho, R. Y. N.; Que, L.; Lambeaux, C.; Fontecave, M. Inorg. Chem. 1999, 38, 1261.(b) Kaczorowska, K.; Kolarska, Z.; Mitka, K.; Kowalski, P. Tetrahedron 2005, 61, 8315.(c) Jayaseeli, A. M. I.; Rajagopal, S. J. Mol. Catal. A: Chem. 2009, 309, 103.

[43] Baciocchi, E.; Gerini, M. F.; Lapi, A. J. Org. Chem. 2004, 69, 3586.

[44] Kerber, W. D.; Ramdhanie, B.; Goldberg, D. P. Angew. Chem., Int. Ed. 2007, 46, 3718.

[45] Rajabi, F.; Naserian, S.; Primo, A.; Luque, R. Adv. Synth. Catal. 2011, 353, 2060.

[46] Villalobos, L.; Ren, T. Inorg. Chem. Commun. 2013, 28, 52.

[47] Mekmouche, Y.; Hummel, H.; Ho, R. Y. N.; Que, L.; Schünemann, V.; Thomas, F. Chem. Eur. J. 2002, 8, 1196.

[48] Legros, J.; Bolm, C. Angew. Chem., Int. Ed. 2003, 42, 5487.

[49] Legros, J.; Bolm, C. Chem. Eur. J. 2005, 11, 1086.

[50] Legros, J.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 4225.

[51] Egami, H.; Katsuki, T. J. Am. Chem. Soc. 2007, 129, 8940.

[52] Maux, P. L.; Simonneaux, G. Chem. Commun. 2011, 47, 6957.

[53] Li, B.; Bai, S.; Wang, P.; Yang, H.; Yang, Q.; Li, C. Phys. Chem. Chem. Phys. 2011, 13, 2504.

[54] (a) Velusamy, S.; Kumar, A. V.; Saini, R.; Punniyamurthy, T. Tetrahedron Lett. 2005, 46, 3819.(b) Kadnikova, E. N.; Kostic, N. M. J. Org. Chem. 2003, 68, 2600.(c) Liu, R.; Wu, L. Z.; Feng, X. M.; Zhang, Z.; Li, Y. Z.; Wang, Z. L. Inorg. Chim. Acta 2007, 360, 656.(d) Kim, K. S.; Hwang, H. J.; Cheong, C. S.; Hahn, C. S. Tetrahedron Lett. 1990, 31, 2893.(e) Chambers, R. D.; Clark, M. Tetrahedron Lett. 1970, 32, 2741.(f) Kirihara, M.; Yamamoto, J.; Noguchi, T.; Itou, A.; Naito, S.; Hirai, Y. Tetrahedron 2009, 65, 10477.

[55] Sharma, S. P.; Suryanarayana, M. V. S.; Nigam, A. K.; Chauhan, A. S.; Tomar, L. N. S. Catal. Commun. 2009, 10, 905.

[56] Rama Raju, B.; Sarkar, S.; Chandramoulali Reddy, U.; Saikia, A. K. J. Mol. Catal. A: Chem. 2009, 308, 169.

[57] (a) Brinksma, J.; La Crois, R.; Feringa, B. L.; Donnoli, M. I.; Rosini. C. Tetrahedron Lett. 2001, 42, 4049.(b) Chen, M.; Patkar, L. N.; Lin, C. J. Org. Chem. 2004, 69, 2884.(c) Barker, J. E.; Ren, T. Tetrahedron Lett. 2004, 45, 4681.(d) Mirkhani, V.; Tangestaninejad, S.; Moghadam, M.; Mohammadpoor-Baltork, I.; Kargar, H. J. Mol. Catal. A: Chem. 2005, 242, 251.

[58] Hosseinpoor, F.; Golchoubian, H. Tetrahedron Lett. 2006, 47, 5195.

[59] Abdolmaleki, A.; Malek-Ahmadi, S. J. Iran. Chem. Soc. 2012, 9, 1015.

[60] Sroura, H.; Jalkha, J.; Mauxa, P. L.; Chevancea, S.; Kobeissib, M.; Simonneauxa, G. J. Mol. Catal. A: Chem. 2013, 370, 75.

[61] Islam, S. K. M.; Roy, A. S.; Mondal, P.; Salam, N.; Paul, S. Catal. Lett. 2013, 143, 225.

[62] Bahrami, K.; Khodaei, M. M.; Yousefi, B. H.; Arabi, M. S. Tetrahedron Lett. 2010, 51, 6939.

[63] Shokrolahi, A.; Zali, A.; Keshavarz, M. H. Chin. J. Catal. 2010, 31, 1427.

[64] Tumula, V. R.; Bondwal, S.; Bisht, P.; Penden, C.; Kumar, J. React. Kinet., Mech. Catal. 2012, 107, 449.

[65] Lindén, A. A.; Krüger, L.; Bäckvall, J.-E. J. Org. Chem. 2003, 68, 5890.

[66] Lindén, A. A.; Johansson, M.; Hermanns, N.; Bäckvall, J.-E. J. Org. Chem. 2006, 71, 3849.

[67] Marsh, B. J.; Carbery, D. R. Tetrahedron Lett. 2010, 51, 2362.

[68] Bakavoli, M.; Kakhky, A. M.; Shiri, A.; Ghabdian, M.; Davoodnia, A.; Eshghi, H.; Khatami, M. Chin. Chem. Lett. 2010, 21, 651.

[69] Rostami, A.; Akradi, J. Tetrahedron Lett. 2010, 51, 3501.

[70] (a) Mojr, V.; Herzig, V.; Buděšínský, M.; Cibulka, R.; Kraus, T. Chem. Commun. 2010, 46, 7599.(b) Mojr, V.; Buděšínský, M.; Cibulka, R.; Kraus, T. Org. Biomol. Chem. 2011, 9, 7318.(c) Hartman, T.; Herzig, V.; Buděšínský, M.; Jind?ich, J.; Cibulka, R.; Kraus, T. Tetrahedron: Asymmetry 2012, 23, 1571.

[71] Huang, Y. B.; Yi, W. B.; Cai, C. J. Fluorine Chem. 2011, 132, 554.

[72] Liu, Z.-M.; Zhao, H.; Li, M.-Q.; Lan, Y.-B.; Yao, Q.-B.; Tao, J.-C.; Wang, X.-W. Adv. Synth. Catal. 2012, 354, 1012 .

[73] Liao, S.; ?ori?, I.; Wang, Q.; List, B. J. Am. Chem. Soc. 2012, 134, 10765.

[74] Iida, H.; Iwahana, S.; Mizoguchi, T.; Yashima, E. J. Am. Chem. Soc. 2012, 134, 15103.

文章导航

/