Citation: 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 shu

Research Progress on Reduction of Sulfoxides to Thiothers

Shanghai Key Laboratory of Materials Protection and Advanced Materials in Electric Power, Shanghai University of Electric Power, Shanghai 200090

Corresponding author: Zou Qi, qzou@shiep.edu.cn Chen Wenbo, wenbochen@shiep.edu.cn
Received Date: 18 January 2019
Revised Date: 30 March 2019
Available Online: 16 September 2019
Fund Project: the Natural Science Foundation of Shanghai City 17ZR1447100the Science and Technology Commission of Shanghai Municipality 14DZ2261000Project supported by the Natural Science Foundation of Shanghai City (No. 17ZR1447100) and the Science and Technology Commission of Shanghai Municipality (No. 14DZ2261000)

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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.
- sulfoxide,
- deoxygenation reduction,
- thioether,
- research progress
1. [1]
  Chen, C.; Li, Y.; Xiao, Y.; Zhu, L.; Cheng, C.; Liu, Y. Chin.J.Org.Chem. 2011, 31, 925(in Chinese).
2. [2]
3. [3]
  Michaelis, A.; Godchaux, E. Ber.1891, 24, 757. doi: 10.1002/cber.189102401145
4. [4]
  Loth, F.; Michaelis, A. Ber.1894, 27, 2540. doi: 10.1002/cber.189402702257
5. [5]
  Madesclaire, M. Tetrahedron Lett.1988, 44, 6537. doi: 10.1016/S0040-4020(01)90096-1
6. [6]
  Still, N.W.J.In Comprehensive Organic Synthesis, Vol.8, Ed.: Trost, B.M., Pergamon Press, Oxford, 1991, p.403.
7. [7]
  Kukushkin, V.Y. Coord.Chem.Rev.1995, 139, 375. doi: 10.1016/0010-8545(94)01116-S
8. [8]
  Firouzabadia, H.; Jamalianb, A. J.Sulfur Chem. 2008, 29, 53. doi: 10.1080/17415990701684776
9. [9]
  Gaumont, A.C.; Gulea, M.S.; Reboul, V. Comprehensive Organic Synthesis II, 2nd ed., Vol.8, Elsevier, Amsterdam, 2014, p.535.
10. [10]
  Shiri, L.; Kazemi, M. Res.Chem.Intermed.2017, 43, 6007. doi: 10.1007/s11164-017-2976-6
11. [11]
  Wakisaka, M.; Hatanaka, M.; Nitta, H.; Hatamura, M.; Ishizuka, T. Synthesis.1980, 67. doi: 10.1055/s-1980-28960
12. [12]
  Faucher, A.; Grand-Maitre, C. Synth.Commun. 2003, 33, 3503. doi: 10.1081/SCC-120024730
13. [13]
  Sanz, R.; Escribano, J.; Aguado, R.; Pedrosa, M.R.; Arnáiz, F.J. Synthesis 2004, 35, 1629. doi: 10.1002/adsc.200600384
14. [14]
  Kikuchi, S.; Konishi, H.; Hashimoto, Y. Tetrahedron Lett. 2005, 61, 3587. doi: 10.1016/j.tet.2005.01.127
15. [15]
  Iranpoor, N.; Firouzabadi, H.; Jamalian, A. Synlett 2005, 36, 1447. doi: 10.1055/s-2005-868488
16. [16]
  Hua, G.; Woollins, J.D. Tetrahedron Lett. 2007, 48, 3677. doi: 10.1016/j.tetlet.2007.03.132
17. [17]
  Bahrami, K.; Khodaei, M.M.; Khedri, M. Chem.Lett.2007, 36, 1324. doi: 10.1246/cl.2007.1324
18. [18]
  Bagherzadeh, M.; Ghazali-Esfahan, S. New J.Chem.2012, 36, 971. doi: 10.1039/c2nj21001k
19. [19]
  Jang, Y.; Kim, K.T.; Jeon, H.B. J.Org.Chem. 2013, 78, 6328. doi: 10.1021/jo4008157
20. [20]
  Ghorbani-Vaghei, R.; Shiri, L.; Ghorbani-Choghamarani, A. C.R.Chim.2014, 17, 1002. doi: 10.1016/j.crci.2013.11.006
21. [21]
  Zhao, X.; Zheng, X.; Yang, B.; Sheng, J.; Lu, K. Org.Biomol.Chem. 2018, 16, 1200. doi: 10.1039/C7OB02834B
22. [22]
  Karimi, B.; Zareyee, D. Synthesis 2003, 34, 335. doi: 10.1055/s-2003-40981
23. [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. doi: 10.1016/j.tetlet.2004.09.068
24. [24]
  Chandra, R.D.; Herbert, B.C. J.Chem.Res.2006, 10, 642.
25. [25]
  Fernandes, A.C.; Carlos, C.R. Tetrahedron Lett.2007, 48, 9176. doi: 10.1016/j.tetlet.2007.10.106
26. [26]
  Zhang, J.; Gao, X.; Zhang, C.; Luan, J.; Zhao, D. Synth.Commun. 2010, 40, 1794. doi: 10.1080/00397910903161819
27. [27]
  Fernandes, A.C.; Fernandes, J.A.; Romao, C.C.; Veiros, L.F.; Calhorda, M.J. Organometallics 2010, 29, 5517. doi: 10.1021/om100450a
28. [28]
  Yakabe, S.; Morimoto, M.T. Synth.Commun.2011, 41, 2251. doi: 10.1080/00397911.2010.501476
29. [29]
  Enthaler, S.; Krackl, S.; Irran, E.; Inoue, S. Catal.Lett. 2012, 142, 1003. doi: 10.1007/s10562-012-0862-9
30. [30]
  Enthaler, S. Catal.Lett. 2012, 142, 1306. doi: 10.1007/s10562-012-0897-y
31. [31]
  Shimizu, M.; Shibuya, K.; Hayakawa, R. Synlett 2000, 10, 1437.
32. [32]
  Firouzabadi, H.; Iranpoor, N.; Jafapour, M. J.Sulf.Chem.2005, 26, 313. doi: 10.1080/17415990500395624
33. [33]
  Ternois, J.; Guillen, F.; Piacenza, G.; Rose, S.J.; Plaquevent, C.; Coquerel, G. Org.Proc.Res.Develop. 2008, 12, 614. doi: 10.1021/op800088x
34. [34]
  Bahrami, K.; Khodaei, M.M.; Karimi, A. Synthesis 2008, 16, 2543. doi: 10.1055/s-2008-1067190
35. [35]
  Bahrami, K.; Khodaei, M.M.; Sheikh, A.M. J.Org.Chem. 2010, 75, 6208. doi: 10.1021/jo1011784
36. [36]
  Bahrami, K.; Khodaei, M.M.; Sohrabnezhad, S. Tetrahedron Lett. 2011, 52, 6420. doi: 10.1016/j.tetlet.2011.09.073
37. [37]
  Zarei, M.; Ameri, A.M.; Jamalian, A. J.Sulfur Chem.2013, 34, 259. doi: 10.1080/17415993.2012.733005
38. [38]
  Atabaki, F.; Abedini, E.; Shokrolahi, A. Phosphorus Sulfur Silicon Relat.Elem.2015, 190, 1169. doi: 10.1080/10426507.2014.978325
39. [39]
  Mohanazadeh, F.; Veisi, H.; Sedrpoushan, A.; Zolfigol, M.A.; Golmohammad, F.; Hemmati, S.; Hashemie, M. J.Sulfur Chem.2014, 35, 7. doi: 10.1080/17415993.2013.801478
40. [40]
  Yoo, B.W.; Park, J.; Shin, H.J.; Yoon, C.M. J.Sulfur Chem.2017, 38, 597. doi: 10.1080/17415993.2017.1337770
41. [41]
  Karimi, B.; Zareyee, D. Synthesis 2003, 1875. doi: 10.1055/s-2003-40981
42. [42]
  Karimi, B.; Zareyee, D. Synthesis 2003, 335. doi: 10.1055/s-2003-37349
43. [43]
  Jabbari, A.; Zarei, M.; Jamaleddini, A. J.Sulfur Chem.2012, 33, 413. doi: 10.1080/17415993.2012.693491
44. [44]
  Abbasi, M.; Mohammadizadeh, M.R.; Moradi, Z. Tetrahedron Lett.2015, 56, 6610. doi: 10.1016/j.tetlet.2015.10.035
45. [45]
  Garcia, N.; Fernandez-Rodriguez, M.A.; Garcia-Garcia, P.; Pedrosa, M.R.; Arnaiz, F.J.; Sanz, R. RSC Adv.2016, 6, 27083. doi: 10.1039/C6RA03106D
46. [46]
  Fernandes, A.C.; Romao, C.C. Tetrahedron 2006, 62, 9650. doi: 10.1016/j.tet.2006.07.077
47. [47]
  Sousa, S.C.A.; Fernandes, A.C. Tetrahedron Lett.2009, 50, 6872. doi: 10.1016/j.tetlet.2009.09.121
48. [48]
  Cabrita, S.I.; Sousa, C.A.; Fernandes, A.C. Tetrahedron Lett.2010, 51, 6132. doi: 10.1016/j.tetlet.2010.09.071
49. [49]
  Enthaler, S.A. Catal.Sci.Technol. 2011, 1, 104. doi: 10.1039/c0cy00039f
50. [50]
  Enthaler, S.; Weidauer, M. Catal.Lett.2011, 141, 833. doi: 10.1007/s10562-011-0590-6
51. [51]
  Enthaler, S. Chem.Cat.Chem. 2011, 3, 666.
52. [52]
  Sousa, S.C.A.; Bernardo, J.R.; Wolff, M.; Machura, B.; Fernandes, A.C. Eur.J.Org.Chem.2014, 46, 1855. doi: 10.1002/ejoc.201301057
53. [53]
  Ding, F.; Jiang, Y.; Gan, S.; Bao, R.L.Y.; Lin, K.; Shi, L. Eur.J.Org.Chem.2017, 24, 3427.
54. [54]
  Porwal, D.; Oestreich, M. Synthesis 2017, 49, 4698. doi: 10.1055/s-0036-1588476
55. [55]
  Firouzabadi, H.; Jamalian, A. Phosphorus Sulfur Relat.Elem.2001, 170, 211. doi: 10.1080/10426500108040599
56. [56]
  Shockravi, A.; Rostami, E.; Heidaryan, D.; Fattahi, H. Iran.J.Chem.Chem.Eng. 2008, 27, 129. doi: 10.1007/s10847-008-9408-6
57. [57]
  Oh, K.; Knabe, W.E. Tetrahedron Lett.2009, 65, 2966. doi: 10.1016/j.tet.2009.02.013
58. [58]
  Yoo, B.W.; Yu, B.R.; Yoon, C.M. J.Sulfur Chem. 2015, 36, 358. doi: 10.1080/17415993.2015.1031234
59. [59]
  Woo, Y.; Byung, S.; Min, S.; Chol, P.M. Synth.Commun. 2007, 37, 3089. doi: 10.1080/00397910701544729
60. [60]
  Yoo, B.W.; Park, M.C.; Song, M.S. Synth.Commun.2007, 37, 4079. doi: 10.1080/00397910600773676
61. [61]
  Yoo, B.W.; Kim, H.M.; Kim, D. Synth.Commun.2013, 43, 2057. doi: 10.1080/00397911.2012.684756
62. [62]
  Yoo, B.W.; Lee, M.K.; Yoon, C.M. Phosphorus Sulfur Silicon Relat.Elem. 2016, 191, 807. doi: 10.1080/10426507.2015.1119147
63. [63]
  Yoo, B.W.; Choi, K.H.; Kim, D.Y.; Choi, K.I.; Kim, J.H. Synth.Commun.2003, 33, 53. doi: 10.1081/SCC-120015558
64. [64]
  Zhang, J.; Gao, X.; Zhang, C.; Luan, J.; Zhao, D. Synth.Commun. 2010, 40, 1794. doi: 10.1080/00397910903161819
65. [65]
  Raju, B.R.; Devi, G.; Nongpluh, Y.S.; Saikia, A.K. Synlett 2005, 358. doi: 10.1055/s-2004-836048
66. [66]
  Khurana, J.M.; Sharma, V.S.; Chacko, A. Tetrahedron Lett. 2007, 63, 966. doi: 10.1016/j.tet.2006.11.027
67. [67]
  Yoo, B.W.; Song, M.S.; Park, M.C. Bull.Korean Chem.Soc.2007, 28, 171. doi: 10.5012/bkcs.2007.28.2.171
68. [68]
  Gurpreet, S.; Bhatia, G.S.; Graczyk, P.P. Tetrahedron Lett. 2004, 45, 5193. doi: 10.1016/j.tetlet.2004.05.049
69. [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. doi: 10.1002/adsc.201100877
70. [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. doi: 10.1039/c3gc36908k
71. [71]
  Abbasi, M.; Mohammadizadeh, M.R.; Moradi, Z. Bull.Chem.Soc.Jpn.2016, 89, 405. doi: 10.1246/bcsj.20150296
72. [72]
  Mitsudome, T.; Takahashi, Y.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Angew.Chem. 2014, 126, 8488. doi: 10.1002/ange.201403425
73. [73]
  Touchy, A.S.; Hakim-Siddiki, S.M.A.; Onodera, W.; Kon, K.; Shimizu, K. Green Chem.2016, 18, 2554. doi: 10.1039/C5GC02806J
74. [74]
  Uematsu, T.; Miyamoto, Y.; Ogasawara, Y.; Suzuki, K.; Yamaguchi, K.; Mizuno, N. Catal.Sci.Technol.2017, 7, 1912. doi: 10.1039/C7CY00547D
75. [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. doi: 10.1039/b313714g
76. [76]
  Nakayama, J.; Tai, A.; Iwasa, S.; Furuya, T.; Sugihara, Y. Tetrahedron Lett. 2005, 46, 1395. doi: 10.1016/j.tetlet.2005.01.057
77. [77]
  Cubbage, J.W.; Tetzlaff, T.A.; Groundwater, H.; McCulla, R.D.; Nag, M.; Jenks, W.S. J.Org.Chem.2001, 66, 8621. doi: 10.1021/jo016134s
78. [78]
  Suzuki, K.; Jeong, J.; Yamaguchi, K.; Mizuno, N. New J.Chem. 2015, 47, 1014. doi: 10.1039/C5NJ01045D
79. [79]
  Sousa, S.C.A.; Bernardo, J.R.; Romao, C.C.; Fernandes, A.C. Tetrahedron Lett.2012, 68, 8194. doi: 10.1016/j.tet.2012.07.071
80. [80]
  Kominami, H.; Nakanishi, K.; Yamamoto, S.; Imamura, K.; Hashimoto, K. Catal.Commun.2014, 54, 100. doi: 10.1016/j.catcom.2014.05.028
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