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
1. [1]
  Xiaoli Deng , Xiangchao Lu , Yang Cao , Qianjin Chen . Electrochemical imaging uncovers the heterogeneity of HER activity by sulfur vacancies in molybdenum disulfide monolayer. Chinese Chemical Letters, 2025, 36(3): 110379-. doi: 10.1016/j.cclet.2024.110379
2. [2]
  Yanhui Lu , Chengang Pei , Wenqiang Li , Qing Liu , Huan Pang , Xu Yu . Tailoring active sites of cerium and nitrogen Co-doped rhenium disulfide for enhanced hydrogen evolution reaction. Chinese Chemical Letters, 2025, 36(12): 111646-. doi: 10.1016/j.cclet.2025.111646
3. [3]
  Jingrong Huang , Xin Ding , Zihan Lin , Yu Lin , Yongqi Liao , Wang Gu , Fa-Jie Chen , Fen-Er Chen . Bromo nitrile oxide-mediated disulfide formation and capping of N-terminal cysteine in peptides. Chinese Chemical Letters, 2026, 37(6): 111715-. doi: 10.1016/j.cclet.2025.111715
4. [4]
  Ping Wang , Ting Wang , Ming Xu , Ze Gao , Hongyu Li , Bowen Li , Yuqi Wang , Chaoqun Qu , Ming Feng . Keplerate polyoxomolybdate nanoball mediated controllable preparation of metal-doped molybdenum disulfide for electrocatalytic hydrogen evolution in acidic and alkaline media. Chinese Chemical Letters, 2024, 35(7): 108930-. doi: 10.1016/j.cclet.2023.108930
5. [5]
  Chaochao Jin , Kai Li , Jiongpei Zhang , Zhihua Wang , Jiajing Tan . N,O-Bidentated difluoroboron complexes based on pyridine-ester enolates: Facile synthesis, post-complexation modification, optical properties, and applications. Chinese Chemical Letters, 2024, 35(9): 109532-. doi: 10.1016/j.cclet.2024.109532
6. [6]
  Yuwei Liang , Jianwei Huang , Zhiqiang Zhang , Qinghong Yang , Aiwen Lei , Hong Yi . Electrochemical Mn-catalyzed nitrogenation of alkynes to nitriles via C≡C bonds cleavage. Chinese Chemical Letters, 2026, 37(4): 111166-. doi: 10.1016/j.cclet.2025.111166
7. [7]
  Yang Li , Yanan Dong , Zhihong Wei , Changzeng Yan , Zhen Li , Lin He , Yuehui Li . Fluoride-promoted Ni-catalyzed cyanation of C–O bond using CO₂ and NH₃. Chinese Chemical Letters, 2025, 36(5): 110206-. doi: 10.1016/j.cclet.2024.110206
8. [8]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
9. [9]
  Shaonan Liu , Shuixing Dai , Minghua Huang . The impact of ester groups on 1,8-naphthalimide electron transport material in organic solar cells. Chinese Journal of Structural Chemistry, 2024, 43(6): 100277-100277. doi: 10.1016/j.cjsc.2024.100277
10. [10]
  Mingpeng Li , Yule Liu , Ziheng Jin , Zhiting Zhao , Bingbing Yan , Ziwen Wang , Qingmin Wang . Recent advances in visible-light-mediated C–S(Ⅵ) bond construction. Chinese Chemical Letters, 2026, 37(11): 112724-. doi: 10.1016/j.cclet.2026.112724
11. [11]
  Zhenjie Yang , Chenyang Hu , Xuan Pang , Xuesi Chen . Sequence design in terpolymerization of ε-caprolactone, CO₂ and cyclohexane oxide: Random ester-carbonate distributions lead to large-span tunability. Chinese Chemical Letters, 2024, 35(5): 109340-. doi: 10.1016/j.cclet.2023.109340
12. [12]
  Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737
13. [13]
  Tong Tong , Lezong Chen , Siying Wu , Zhong Cao , Yuanbin Song , Jun Wu . Establishment of a leucine-based poly(ester amide)s library with self-anticancer effect as nano-drug carrier for colorectal cancer treatment. Chinese Chemical Letters, 2024, 35(12): 109689-. doi: 10.1016/j.cclet.2024.109689
14. [14]
  Qiang Feng , Jindong Hao , Ya Hu , Rong Fu , Wei Wei , Dong Yi . Photocatalytic multi-component synthesis of ester-containing quinoxalin-2(1H)-ones using water as the hydrogen donor. Chinese Chemical Letters, 2025, 36(6): 110582-. doi: 10.1016/j.cclet.2024.110582
15. [15]
  Caili Xu , Ming Zhang , Pengyu Li , Cheng Chen , Haiping Zhou , Shu Zhang , Mengqiang Wu . Fluorinated ester additive-assisted carbonate-based electrolyte enhances low temperature operation of LiFePO₄ batteries. Chinese Chemical Letters, 2026, 37(8): 111263-. doi: 10.1016/j.cclet.2025.111263
16. [16]
  Junmeng Luo , Qiongqiong Wan , Suming Chen . Chemistry-driven mass spectrometry for structural lipidomics at the C=C bond isomer level. Chinese Chemical Letters, 2025, 36(1): 109836-. doi: 10.1016/j.cclet.2024.109836
17. [17]
  Tian-Zhang Wang , Le-Yu Tang , Yu-Qiu Guan , Lingfei Hu , Gang Lu , Yu-Feng Liang . Nickel-catalyzed reductive alkynylation of ketoimines via unstrained C–C bond activation. Chinese Chemical Letters, 2025, 36(11): 111050-. doi: 10.1016/j.cclet.2025.111050
18. [18]
  Shan-Shan Li , Juan Luo , Shu-Nuo Liang , Dan-Na Chen , Li-Ning Chen , Cheng-Xue Pan , Peng-Ju Xia . Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy. Chinese Chemical Letters, 2025, 36(6): 110424-. doi: 10.1016/j.cclet.2024.110424
19. [19]
  Jing Ren , Feng-Huan Du , Xiaowei Chen , Chi Zhang . Monofluoroiodane(Ⅲ) reagent mediated Wagner−Meerwein rearrangement fluorination: Construction of quaternary C(sp³)−F bond. Chinese Chemical Letters, 2026, 37(5): 111407-. doi: 10.1016/j.cclet.2025.111407
20. [20]
  Yanjie Lv , Xinyu Zhao , Jing Sun , Huiying Sun , Wenxi Zhang , Yuhan Cui , Xiao Li , Zhongmin Su . Atomic-level regulation of POMOF homologous isomer for photocatalytic C-H bond oxidation. Chinese Chemical Letters, 2026, 37(10): 113018-. doi: 10.1016/j.cclet.2026.113018

Get Citation

PDF

XML

Metrics

PDF Downloads(23)
Abstract views(2413)
HTML views(288)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142