Citation: Liu Aiyao, Liu Jiang, Mei Haibo, Gerd-Volker Röschenthaler, Han Jianlin. Selectfluor-Promoted Twofold Sulfination of Alcohols for the Synthesis of Sulfinic Ester from Diaryldisulfides[J]. Chinese Journal of Organic Chemistry, ;2020, 40(7): 1926-1933. doi: 10.6023/cjoc202003004 shu

Selectfluor-Promoted Twofold Sulfination of Alcohols for the Synthesis of Sulfinic Ester from Diaryldisulfides

a.
Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
b.
Shandong Key Laboratory of Biochemical Analysis, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
c.
Department of Life Sciences and Chemistry, Jacobs University Bremen gGmbH, Bremen 28759, Germany

Corresponding author: Mei Haibo, meihb@njfu.edu.cn Han Jianlin, hanjl@njfu.edu.cn
Received Date: 3 March 2020
Revised Date: 6 May 2020
Available Online: 15 May 2020
Fund Project: the German Research Foundation 362/74-1the National Natural Science Foundation of China 21761132021Project supported by the National Natural Science Foundation of China (No. 21761132021), the German Research Foundation (No. 362/74-1) and the Open Project of Chemistry Department of Qingdao University of Science and Technology (No. QUSTHX202005)the Open Project of Chemistry Department of Qingdao University of Science and Technology QUSTHX202005

Figures(4)

An oxidative twofold sulfination of alcohol with Selectfluor as an efficient oxidant was developed. This reaction proceeded smoothly achieving the unprecedented sulfination transformation of varieties of diaryldisulfides and alcohols under simple conditions, affording the corresponding sulfinic esters in excellent yields. The current reaction provides a new and convenient strategy for the preparation of sulfinic esters.
- Selectfluor,
- disulfide,
- sufination,
- sulfinic ester,
- C-O bond cleavage
1. [1]
2. [2]
  (a) Allison, W. S. Acc. Chem. Res. 1976, 9, 293.
  (b) Kim, J. H.; Lee, J. O.; Lee, S. K.; Moon, J. W.; You, G. Y.; Kim, S. J.; Park, S.-H.; Park, J. M.; Lim, S. Y.; Suh, P.-G.; Uhm, K.-O.; Song, M. S.; Kim, H. S. J. Biol. Chem. 2011, 286, 7567.
  (c) Jönsson, T. J.; Murray, M. S.; Johnson, L. C.; Lowther, W. T. J. Biol. Chem. 2008, 283, 23846.
3. [3]
  (a) Douglass, I. B. J. Org. Chem. 1965, 30, 633.
  (b) Douglass, I. B.; Ward, F. J.; Norton, R. V. J. Org. Chem. 1967, 32, 324.
  (c) Hajipour, A. R.; Falahati, A. R.; Ruoho, A. E. Tetrahedron Lett. 2006, 47, 2717.
  (d) Fernandez, I.; Khiar, N.; Roca, A.; Benabra, A.; Alcudia, A.; Espartero, J. L.; Alcudia, F. Tetrahedron Lett. 1999, 40, 2029.
4. [4]
  Toshikazu, T.; Shigeru, O. Bull. Chem. Soc. Jpn. 1982, 55, 3937. doi: 10.1246/bcsj.55.3937
5. [5]
  D'Oca, M. G. M.; Russowsky, D.; Canto, K.; Gressler, T.; Goncüalves, R. S. Org. Lett. 2002, 4, 1763. doi: 10.1021/ol0258381
6. [6]
  Tranquilino, A.; Andrade, S. R. C. P.; da Silva, A. P. M.; Menezes, P. H.; Oliveira, R. A. Tetrahedron Lett. 2017, 58, 1265.
7. [7]
  (a) Field, L.; Hoelzel, C. B.; Locke, J. M. J. Am. Chem. Soc. 1962, 84, 847.
  (b) Brownbridge, P.; Jowett, I. C. Synthesis 1988, 252.
  (c) Xia, M.; Chen, Z. C. Synth. Commun. 1997, 27, 1301.
  (d) Zhou, C.; Tan, Z.; Jiang, H.; Zhang, M. Green Chem. 2018, 20, 1992.
  (e) Douglass, I. B. J. Org. Chem. 1973, 39, 563.
  (f) Brownbridge, P.; Jowett, I. C. Synthesis 1988, 252.
  (g) Wei, J.; Sun, Z. Org. Lett. 2015, 17, 5396.
8. [8]
  (a) Du, B.; Li, Z.; Qian, P.; Han, J. L.; Pan, Y. Chem.-Asian J. 2016, 11, 478.
  (b) Du, B.; Wang, W.; Wang, Y.; Qi, Z.; Tian, J.; Zhou, J.; Wang, X.; Han, J. L.; Ma, J.; Pan, Y. Chem.-Asian J. 2018, 13, 404.
9. [9]
  (a) Ai, C.; Shen, H.; Song, D.; Li, Y.; Yi, X.; Wang, Z.; Ling, F.; Zhong, W. Green Chem. 2019, 21, 5528.
  (b) Gong, F.; Ju, F.; Zuo, L.; Wang, Q.; Li, R.; Hu, J.; Li, Z.; Takfaoui, A.; Lei, A. J. Chin. Chem. Soc. 2020, 67, 192.
10. [10]
  (a) He, Y.; Zhang, J.; Xu, L.; Wei, Y. Tetrahedron Lett. 2020, 61, 151631.
  (b) Lavey, C. F.; Hesk, D.; Hendershot, S.; Koharski, D.; Saluja, S.; Namara, P. M. J. Labelled Compd. Radiopharm. 2007, 50, 264.
  (c) Ji, Y.; Wang, M.; Li, H.; Liu, Y.; Wu, Y. Eur. J. Org. Chem. 2016, 4077.
  (d) Dahn, H.; Toan, V. V.; Ung-Truong, M. Magn. Reson. Chem. 1991, 29, 897.
11. [11]
  Nyffeler, P. T.; Durόn, S. G.; Burkart, M. D.; Vincent, S. P.; Wong, C. H. Angew. Chem., Int. Ed. 2005, 44, 192. doi: 10.1002/anie.200400648
12. [12]
  (a) Cheng, H. G.; Yin, G. Chem 2019, 5, 1022.
  (b) Szpera, R.; Moseley, D. F. J.; Smith, L. B.; Sterling, A. J.; Gouverneur, V. Angew. Chem., Int. Ed. 2019, 58, 14824.
  (c) Wood, S. H.; Etridge, S.; Kennedy, A. R.; Percy, J. M.; Nelson, D. J. Chem.-Eur. J. 2019, 25, 5574.
  (d) Xu, J.; Kuang, Z.; Song, Q. Chin. Chem. Lett. 2018, 29, 963.
  (e) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728.
  (f) Mei, H.; Remete, A. M.; Zou, Y.; Moriwaki, H.; Fustero, S.; Kiss, L.; Soloshonok, V. A.; Han, J. Chin. Chem. Lett. 2020, DOI: org/10.1016/j.cclet.2020.03.050.
13. [13]
  (a) Niu, L.; Liu, J.; Liang, X. A.; Wang, S.; Lei, A. Nat. Commun. 2019, 10, 467.
  (b) Liang, X. A.; Niu, L.; Wang, S.; Liu, J.; Lei, A. Org. Lett. 2019, 21, 2441.
  (c) Xie, L. Y.; Qiu, J.; Peng, S.; Liu, K. J.; Wang, Z.; Ding, M. H.; Wang, Y.; Cao, Z.; He, W. M. Green Chem. 2018, 20, 760.
  (d) Zhou, J.; Zou, Y.; Zhou, P.; Chen, Z.; Li, J. Org. Chem. Front. 2019, 6, 1594.
  (e) Xie, L. Y.; Peng, S.; Liu, F.; Yi, J. Y.; Wang, M.; Tang, Z.; Xu, X.; He, W. M. Adv. Synth. Catal. 2018, 360, 4259.
  (f) Galloway, J. D.; Mai, D. N.; Baxter, R. D. Org. Lett. 2017, 19, 5772.
  (g) Wang, C. X.; Cai, J. W.; Zhang, M.; Zhao, X. M. J. Org. Chem. 2017, 82, 1260.
  (h) Zhou, G.; Tian, Y. W.; Zhao, X. M.; Dan, W. Y. Org. Lett. 2018, 20, 4858.
  (i) Hu, J.; Zhou, G.; Tian, Y.; Zhao, X. Org. Biomol. Chem. 2019, 17, 6342.
  (j) Yuan, J. W.; Zhu, J. L.; Li, B.; Yang, L. Y.; Mao, P.; Zhang, S. R.; Li, Y. C.; Qu, L. B. Org. Biomol. Chem. 2019, 17, 10178.
  (k) Yuan, J.; Zeng, F.; Mai, W.; Yang, L.; Xiao, Y.; Mao, P.; Wei, D. Org. Biomol. Chem. 2019, 17, 5038.
  (l) Mai, W. P.; Yuan, J. W.; Zhu, J. L.; Li, Q. Q.; Yang, L. R.; Xiao, Y. M.; Mao, P.; Qu, L. B. ChemistrySelect 2019, 4, 11066.
  (m) Mei, H. B.; Liu, J.; Pajkert, R.; Röschenthaler, G. V.; Han, J. L. Org. Biomol. Chem. 2020, 18, 3761.
14. [14]
  Yadav, J. S.; Reddy, B. V. S.; Reddy, Y. J. Tetrahedron Lett. 2007, 48, 7034. doi: 10.1016/j.tetlet.2007.07.130
15. [15]
  Kirihara, M.; Naito, S.; Ishizuka, Y.; Hanai, H.; Noguchi, T. Tetrahedron Lett. 2011, 52, 3086. doi: 10.1016/j.tetlet.2011.03.132
16. [16]
  Vincent, S. P.; Burkart, M. D.; Tsai, C. Y.; Zhang, Z.; Wong, C. H. J. Org. Chem. 1999, 64, 5264.
17. [17]
  Tota, A.; John-Campbell, S. S.; Briggs, E. L.; Estévez, G. O.; Afonso, M.; Degennaro, L.; Luisi, R.; Bull, J. A. Org. Lett. 2018, 20, 2599. doi: 10.1021/acs.orglett.8b00788
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1.
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