Reviews

Recent Progress on Synthesis of Sulfur Compounds by Sodium Sulfinates

  • Huang Guobao ,
  • Li Xiuying ,
  • Luo Jinrong ,
  • Luo Zhihui ,
  • Tan Minxiong
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  • Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology, Yulin Normal University, Yulin 537000

Received date: 2018-09-25

  Revised date: 2018-10-28

  Online published: 2018-11-26

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21761033, 21565028), the Natural Science Foundation of Guangxi (No. 2017GXNSFBA198211), and the Yulin Normal University Research Grant (No. 2018YJKY36).

Abstract

Sodium sulfinates (RSO2Na) is a kind of reagents with stable properties, simple synthesis and low price, which has been widely used in the field of organic synthesis chemistry. The recent progress (2014~2018) on synthesis of sulfur compounds by sodium sulfinates is summarized. In addition, the organic reactions on the building of S-X (S-S, S-N and S-P bond) and other types of reactions are described respectively, with their scope of substrates and reaction mechanism. It is hoped that this review can be referred to the future application in organic synthesis of sodium sulfinates.

Cite this article

Huang Guobao , Li Xiuying , Luo Jinrong , Luo Zhihui , Tan Minxiong . Recent Progress on Synthesis of Sulfur Compounds by Sodium Sulfinates[J]. Chinese Journal of Organic Chemistry, 2019 , 39(3) : 617 -624 . DOI: 10.6023/cjoc201809030

References

[1] (a) Reddy, M.; Reddy, S.-P.; Sreedhara, B. Adv. Synth. Catal. 2010, 352, 1861.
(b) Li, Y.; Cheng, K.; Lu, X.; Sun, J. Adv. Synth. Catal. 2010, 352, 1876.
(c) Rao, H.; Yang, L.; Shuai, Q.; Lia, C. Adv. Synth. Catal. 2011, 353, 1701.
(d) Li, S. M. S. Thesis, Zhengzhou University, Zhengzhou, 2015 (in Chinese). (李莎, 硕士论文, 郑州大学, 郑州, 2015).
(e) Hui, R.; Zhang, S.; Tan, Z.; Wu, X.; Feng, B. Chin. J. Org. Chem. 2017, 37, 3060(in Chinese). (惠人杰, 张士伟, 谭政, 吴小培, 冯柏年, 有机化学, 2017, 37, 3060.)
(f) Ueda, M.; Hartwig, J.-F. Org. Lett. 2010, 12, 92.
(g) Maloney, K.-M.; Kuethe, J.-T.; Linn, K. Org. Lett., 2011, 13, 102
[2] (a) Uttamchandani, M.; Liu, K.; Panicker, R. C.; Yao, S. Q. Chem. Commun. 2007, 1518.
(b) Steert, K.; El-Sayed, I.; Van der Veken, P.; Krishtal, A.; Van Alsenoy, C.; Westrop, G. D.; Mottram, J. C.; Coombs, G. H.; Augustyns, K.; Haemers, A. Bioorg. Med. Chem. Lett. 2007, 17, 6563.
(c) Ettari, R.; Nizi, E.; Francesco, M. E. D.; Dude, M.-A.; Pradel, G.; Vicík, R.; Schirmeister, T.; Micale, N.; Grasso, S.; Zappalà, M. J. Med. Chem. 2008, 51, 988.
(d) Curti, C.; Laget, M.; Carle, A. O.; Gellis, A.; Vanelle, P. Eur. J. Med. Chem. 2007, 42, 880.
[3] Meesin, J.; Katrun, P.; Pareseecharoen, C.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Kuhakarn, C. J. Org. Chem. 2016, 81, 2744.
[4] Sun, Y.; Abdukader, A.; Lu, D.; Zhang, H.; Liu, C. Green Chem. 2017, 19, 1255.
[5] Xiong, Y.; Weng, J.; Lu, L. Adv. Synth. Catal. 2018, 360, 1611.
[6] Xu, Y.; Zhao, J.; Tang, X.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2014, 356, 2029.
[7] Jiang, Q.; Xu, B.; Jia, J.; Zhao, A.; Zhao, Y.; Li, Y.; He, N.; Guo, C. J. Org. Chem. 2014, 79, 7372.
[8] Meyer, A.; Jäger, S.; Hari, D.; König, B. Adv. Synth. Catal. 2015, 357, 2050.
[9] Habibi, D.; Rahimi, A.; Rostami, A.; Moradi, S. Tetrahedron Lett. 2017, 58, 289.
[10] Feng, M.; Xi, L.; Chen, S.; Yu, X. Eur. J. Org. Chem. 2017, 2746.
[11] Wu, W.; Yi, S.; Huang, W.; Luo, D.; Jiang, H. Org. Lett. 2017, 19, 2825.
[12] Sun, D.; Zhang, R. Org. Chem. Front., 2018, 5, 92.
[13] Xie, L.; Peng, S.; Liu, F.; Chen, G.; Xia, W.; Yu, X.; Li, W.; Cao, Z.; He, W. Org. Chem. Front. 2018, 5, 2604.
[14] Johnson, T.; Elbert, B.; Farley, A.; Gorman, T.; Genicot, C.; Lallemand, B.; Pasau, P.; Flasz, J.; Castro, J.; MacCoss, M.; Dixon, D.; Paton, R.; Schofield, C.; Smith, M.; Willis, M. Chem. Sci. 2018, 9, 629.
[15] Li, W.; Chen, Y.; Lam, Y. Tetrahedron Lett. 2004, 45, 6545.
[16] Xiao, F.; Liu, C.; Yuan, S.; Huang, H.; Deng, G. J. Org. Chem. 2018, 83, 10420.
[17] Li, L.; Dong, D.; Hao, S.; Wang, Z. Tetrahedron Lett. 2018, 59, 1517.
[18] Zhu, Y.; Gong, Y. Tetrahedron 2016, 72, 3436.
[19] Cao, L.; Luo, S.; Jiang, K.; Hao, Z.; Wang, B.; Pang, C.; Wang, Z. J. Org. Chem. 2018, 20, 4754.
[20] Lin, Y.; Yi, W. Chin. J. Org. Chem. 2018, 38, 1207. (in Chinese). (林雅玫, 易文斌有机化学, 2018, 38, 1207.)
[21] Tang, X.; Huang, L.; Qi, C.; Wu, X.; Wu, W. Q.; Jiang, H. Chem. Commun. 2013, 49, 6102.
[22] Pan, X.; Gao, J.; Liu, J.; Lai, J.; Jiang, H.; Yuan, G. Green Chem. 2015, 17, 1400.
[23] Lai, J.; Chang, L.; Yuan, G. Org. Lett. 2016, 18, 3194.
[24] Rahimi, A.; Habibi, D.; Rostami, A.; Zolfigol, M.; Mallakpour, S. Tetrahedron Lett. 2018, 59, 383.
[25] Lin, Y.; Lu, G.; Wang, G.; Yi, W. J. Org. Chem. 2017, 82, 382.

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