Chinese Journal of Organic Chemistry >
Research Progress on Reduction of Sulfoxides to Thiothers
Received date: 2019-01-18
Revised date: 2019-03-30
Online published: 2019-04-16
Supported by
Project supported by the Natural Science Foundation of Shanghai City (No. 17ZR1447100) and the Science and Technology Commission of Shanghai Munic-ipality (No. 14DZ2261000).
As one of the most important transformations in organic synthesis, deoxygenation reduction of sulfoxides to thioethers has attracted wide attention in researches and applications. With the development of organicmetallic chemistry, many mild and practical methods have been developed to reduce sulfoxides. In this review, based on the types of the reducing agents, the research progress on the deoxygenation reduction of sulfoxides to thiothers in recent 20 years is summarized. In addition, the advantages and disadvantages of these reduction systems, some reaction mechanisms and the prospects of research in this field are discussed.
Key words： sulfoxide; deoxygenation reduction; thioether; research progress
Li Weilin , Chen Xuanying , Zheng Tianjiao , Zou Qi , Chen Wenbo . Research Progress on Reduction of Sulfoxides to Thiothers[J]. Chinese Journal of Organic Chemistry, 2019 , 39(9) : 2443 -2457 . DOI: 10.6023/cjoc201901028
[1] Chen, C.; Li, Y.; Xiao, Y.; Zhu, L.; Cheng, C.; Liu, Y. Chin. J. Org. Chem. 2011, 31, 925(in Chinese). (陈春玉, 李毅, 肖英, 朱林, 程长明, 刘杨, 有机化学, 2011, 31, 925.)
[2] (a) McGarrigle, E. M.; Myers, E. L.; Illa, O.; Shaw, M. A.; Riches, S. L.; Aggarwal, V. K. Chem. Rev. 2007, 107, 5841.
(b) Rickard, D.; Luther Ⅲ, G. W. Chem. Rev. 2007, 107, 514.
[3] Michaelis, A.; Godchaux, E. Ber. 1891, 24, 757.
[4] Loth, F.; Michaelis, A. Ber. 1894, 27, 2540.
[5] Madesclaire, M. Tetrahedron Lett. 1988, 44, 6537.
[6] Still, N. W. J. In Comprehensive Organic Synthesis, Vol. 8, Ed.:Trost, B. M., Pergamon Press, Oxford, 1991, p. 403.
[7] Kukushkin, V. Y. Coord. Chem. Rev. 1995, 139, 375.
[8] Firouzabadia, H.; Jamalianb, A. J. Sulfur Chem. 2008, 29, 53.
[9] Gaumont, A. C.; Gulea, M. S.; Reboul, V. Comprehensive Organic Synthesis Ⅱ, 2nd ed., Vol. 8, Elsevier, Amsterdam, 2014, p. 535.
[10] Shiri, L.; Kazemi, M. Res. Chem. Intermed. 2017, 43, 6007.
[11] Wakisaka, M.; Hatanaka, M.; Nitta, H.; Hatamura, M.; Ishizuka,T. Synthesis. 1980, 67.
[12] Faucher, A.; Grand-Maitre, C. Synth. Commun. 2003, 33, 3503.
[13] Sanz, R.; Escribano, J.; Aguado, R.; Pedrosa, M. R.; Arnáiz, F. J. Synthesis 2004, 35, 1629.
[14] Kikuchi, S.; Konishi, H.; Hashimoto, Y. Tetrahedron Lett. 2005, 61, 3587.
[15] Iranpoor, N.; Firouzabadi, H.; Jamalian, A. Synlett 2005, 36, 1447.
[16] Hua, G.; Woollins, J. D. Tetrahedron Lett. 2007, 48, 3677.
[17] Bahrami, K.; Khodaei, M. M.; Khedri, M. Chem. Lett. 2007, 36, 1324.
[18] Bagherzadeh, M.; Ghazali-Esfahan, S. New J. Chem. 2012, 36, 971.
[19] Jang, Y.; Kim, K. T.; Jeon, H. B. J. Org. Chem. 2013, 78, 6328.
[20] Ghorbani-Vaghei, R.; Shiri, L.; Ghorbani-Choghamarani, A. C. R. Chim. 2014, 17, 1002.
[21] Zhao, X.; Zheng, X.; Yang, B.; Sheng, J.; Lu, K. Org. Biomol. Chem. 2018, 16, 1200.
[22] Karimi, B.; Zareyee, D. Synthesis 2003, 34, 335.
[23] Harrison, D. J.; Tam, N. C.; Vogels, C. M.; Langler, R. F.; Baker, R. T.; Deckenc, A.; Westcott, S. A. Tetrahedron Lett. 2004, 45, 8493.
[24] Chandra, R. D.; Herbert, B. C. J. Chem. Res. 2006, 10, 642.
[25] Fernandes, A. C.; Carlos, C. R. Tetrahedron Lett. 2007, 48, 9176.
[26] Zhang, J.; Gao, X.; Zhang, C.; Luan, J.; Zhao, D. Synth. Commun. 2010, 40, 1794.
[27] Fernandes, A. C.; Fernandes, J. A.; Romao, C. C.; Veiros, L. F.; Calhorda, M. J. Organometallics 2010, 29, 5517.
[28] Yakabe, S.; Morimoto, M. T. Synth. Commun. 2011, 41, 2251.
[29] Enthaler, S.; Krackl, S.; Irran, E.; Inoue, S. Catal. Lett. 2012, 142, 1003.
[30] Enthaler, S. Catal. Lett. 2012, 142, 1306.
[31] Shimizu, M.; Shibuya, K.; Hayakawa, R. Synlett 2000, 10, 1437.
[32] Firouzabadi, H.; Iranpoor, N.; Jafapour, M. J. Sulf. Chem. 2005, 26, 313.
[33] Ternois, J.; Guillen, F.; Piacenza, G.; Rose, S. J.; Plaquevent, C.; Coquerel, G. Org. Proc. Res. Develop. 2008, 12, 614.
[34] Bahrami, K.; Khodaei, M. M.; Karimi, A. Synthesis 2008, 16, 2543.
[35] Bahrami, K.; Khodaei, M. M.; Sheikh, A. M. J. Org. Chem. 2010, 75, 6208.
[36] Bahrami, K.; Khodaei, M. M.; Sohrabnezhad, S. Tetrahedron Lett. 2011, 52, 6420.
[37] Zarei, M.; Ameri, A. M.; Jamalian, A. J. Sulfur Chem. 2013, 34, 259.
[38] Atabaki, F.; Abedini, E.; Shokrolahi, A. Phosphorus Sulfur Silicon Relat. Elem. 2015, 190, 1169.
[39] Mohanazadeh, F.; Veisi, H.; Sedrpoushan, A.; Zolfigol, M. A.; Golmohammad, F.; Hemmati, S.; Hashemie, M. J. Sulfur Chem. 2014, 35, 7.
[40] Yoo, B. W.; Park, J.; Shin, H. J.; Yoon, C. M. J. Sulfur Chem. 2017, 38, 597.
[41] Karimi, B.; Zareyee, D. Synthesis 2003, 1875.
[42] Karimi, B.; Zareyee, D. Synthesis 2003, 335.
[43] Jabbari, A.; Zarei, M.; Jamaleddini, A. J. Sulfur Chem. 2012, 33, 413.
[44] Abbasi, M.; Mohammadizadeh, M. R.; Moradi, Z. Tetrahedron Lett. 2015, 56, 6610.
[45] Garcia, N.; Fernandez-Rodriguez, M. A.; Garcia-Garcia, P.; Pedrosa, M. R.; Arnaiz, F. J.; Sanz, R. RSC Adv. 2016, 6, 27083.
[46] Fernandes, A. C.; Romao, C. C. Tetrahedron 2006, 62, 9650.
[47] Sousa, S. C. A.; Fernandes, A. C. Tetrahedron Lett. 2009, 50, 6872.
[48] Cabrita, S. I.; Sousa, C. A.; Fernandes, A. C. Tetrahedron Lett. 2010, 51, 6132.
[49] Enthaler, S. A. Catal. Sci. Technol. 2011, 1, 104.
[50] Enthaler, S.; Weidauer, M. Catal. Lett. 2011, 141, 833.
[51] Enthaler, S. Chem. Cat. Chem. 2011, 3, 666.
[52] Sousa, S. C. A.; Bernardo, J. R.; Wolff, M.; Machura, B.; Fer-nandes, A. C. Eur. J. Org. Chem. 2014, 46, 1855.
[53] Ding, F.; Jiang, Y.; Gan, S.; Bao, R. L. Y.; Lin, K.; Shi, L. Eur. J. Org. Chem. 2017, 24, 3427.
[54] Porwal, D.; Oestreich, M. Synthesis 2017, 49, 4698.
[55] Firouzabadi, H.; Jamalian, A. Phosphorus Sulfur Relat. Elem. 2001, 170, 211.
[56] Shockravi, A.; Rostami, E.; Heidaryan, D.; Fattahi, H. Iran. J. Chem. Chem. Eng. 2008, 27, 129.
[57] Oh, K.; Knabe, W. E. Tetrahedron Lett. 2009, 65, 2966.
[58] Yoo, B. W.; Yu, B. R.; Yoon, C. M. J. Sulfur Chem. 2015, 36, 358.
[59] Woo, Y.; Byung, S.; Min, S.; Chol, P. M. Synth. Commun. 2007, 37, 3089.
[60] Yoo, B. W.; Park, M. C.; Song, M. S. Synth. Commun. 2007, 37, 4079.
[61] Yoo, B. W.; Kim, H. M.; Kim, D. Synth. Commun. 2013, 43, 2057.
[62] Yoo, B. W.; Lee, M. K.; Yoon, C. M. Phosphorus Sulfur Silicon Relat. Elem. 2016, 191, 807.
[63] Yoo, B. W.; Choi, K. H.; Kim, D. Y.; Choi, K. I.; Kim, J. H. Synth. Commun. 2003, 33, 53.
[64] Zhang, J.; Gao, X.; Zhang, C.; Luan, J.; Zhao, D. Synth. Commun. 2010, 40, 1794.
[65] Raju, B. R.; Devi, G.; Nongpluh, Y. S.; Saikia, A. K. Synlett 2005, 358.
[66] Khurana, J. M.; Sharma, V. S.; Chacko, A. Tetrahedron Lett. 2007, 63, 966.
[67] Yoo, B. W.; Song, M. S.; Park, M. C. Bull. Korean Chem. Soc. 2007, 28, 171.
[68] Gurpreet, S.; Bhatia, G. S.; Graczyk, P. P. Tetrahedron Lett. 2004, 45, 5193.
[69] Garcia, N.; Garcia-Garcia, P.; Fernandez-Rodriguez, M. A.; Rubio, R.; Pedrosa, M. R.; Arnaiz, F. J.; Sanz, R. Adv. Synth. Catal. 2012, 354, 321.
[70] Garcia, N.; Garcia-Garcia, P.; Fernandez-Rodriguez, M. A.; Rubio, R. M.; Pedrosa, R.; Arnaiz, F. J.; Sanz, R. Green Chem. 2013, 15, 999.
[71] Abbasi, M.; Mohammadizadeh, M. R.; Moradi, Z. Bull. Chem. Soc. Jpn. 2016, 89, 405.
[72] Mitsudome, T.; Takahashi, Y.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Angew. Chem. 2014, 126, 8488.
[73] Touchy, A. S.; Hakim-Siddiki, S. M. A.; Onodera, W.; Kon, K.; Shimizu, K. Green Chem. 2016, 18, 2554.
[74] Uematsu, T.; Miyamoto, Y.; Ogasawara, Y.; Suzuki, K.; Yamaguchi, K.; Mizuno, N. Catal. Sci. Technol. 2017, 7, 1912.
[75] Sharma, D. R.; Alistair, N. D.; King, W. T.; Shepherd, S. D.; Christopher, C. R.; Allen, R. A.; Holt, H. R. L.; Howard, D. Org. Biomol. Chem. 2004, 2, 554.
[76] Nakayama, J.; Tai, A.; Iwasa, S.; Furuya, T.; Sugihara, Y. Tetrahedron Lett. 2005, 46, 1395.
[77] Cubbage, J. W.; Tetzlaff, T. A.; Groundwater, H.; McCulla, R. D.; Nag, M.; Jenks, W. S. J. Org. Chem. 2001, 66, 8621.
[78] Suzuki, K.; Jeong, J.; Yamaguchi, K.; Mizuno, N. New J. Chem. 2015, 47, 1014.
[79] Sousa, S. C. A.; Bernardo, J. R.; Romao, C. C.; Fernandes, A. C. Tetrahedron Lett. 2012, 68, 8194.
[80] Kominami, H.; Nakanishi, K.; Yamamoto, S.; Imamura, K.; Hashimoto, K. Catal. Commun. 2014, 54, 100.
/
| 〈 |
|
〉 |
