原位产生二氧化锰催化构建S—S键

doi:10.6023/cjoc201912045

有机化学 ›› 2020, Vol. 40 ›› Issue (8): 2483-2490.DOI: 10.6023/cjoc201912045 上一篇下一篇

研究论文

原位产生二氧化锰催化构建S—S键

吕进强, 曾竟, 阿布都热西提·阿布力克木

新疆师范大学化学系乌鲁木齐 830054

收稿日期:2019-12-31 修回日期:2020-05-12 发布日期:2020-05-20
通讯作者: 阿布都热西提·阿布力克木, 曾竟 E-mail:aarexit@xjnu.edu.cn;zengjing800111@163.com
基金资助:
新疆维吾尔自治区高校科研计划自然科学重点项目（No.XJEDU2020I015）和新疆维吾尔自治区2017年自治区“天山青年计划”（No.2017Q026）资助项目.

Highly Active Manganese Dioxide Catalyzed the Construction of S-S Bond

Lü Jinqiang, Zeng Jing, Abulikemu Abudu Rexit

Department of Chemistry, Xinjiang Normal University, Urumqi 830054

Received:2019-12-31 Revised:2020-05-12 Published:2020-05-20
Supported by:
Project supported by the Scientific Research Program of the Higher Education Institution of Xinjiang (No. XJEDU2020I015), and the Xinjiang Tianshan Youth Program (No. 2017Q026).

文章分享

1. cjoc201912045辅助材料.pdf(3388KB)

摘要/Abstract

利用0.1~0.2 equiv.高锰酸钾在无水乙醇体系中原位生成高活性二氧化锰，并以此为催化剂，促使硫酚、硫醇类化合物在室温下发生自由基自身偶联反应构建S—S键，获得了14种对称双硫化物，产率介于70%~99%；同时发现该催化体系还可催化对称双硫化物与不同取代基的硫酚、硫醇或两个不同的对称双硫化物，发生自由基交叉偶联反应合成了13个不对称双硫化合物，产率19%~72%.该法具有简单高效、后处理简单、绿色溶剂、底物适用范围广、条件温和等优点，所有产物均经¹H NMR、¹³C NMR结构确证.

关键词: 自由基偶联反应, S-S键, 二氧化锰

Generation of highly active manganese dioxide in situ by using catalytic amount of potassium permanganate in anhydrous ethanol system, the catalytic system promoted S-S bond construction by free radical self coupling reactions of thiophenol and mercaptan compounds at room temperature. 14 disulfides were obtained with 70%~99% yields. At the same time, it was also found that the catalytic system could also catalyze radical cross-coupling reactions between symmetric disulfides and different substituents of thiophenols, thiols, or two different symmetric disulfides, 13 asymmetric disulfides were obtained with 19%~72% yields. The protocol offered the advantages of simple and efficient, easy separation, green solvent, wide range of substrate applications, and mild conditions. All products were confirmed by ¹H NMR and ¹³C NMR spectra.

Key words: free radical coupling reaction, S-S bond, manganese dioxide

引用此文

吕进强, 曾竟, 阿布都热西提·阿布力克木. 原位产生二氧化锰催化构建S—S键[J]. 有机化学, 2020, 40(8): 2483-2490.

Lü Jinqiang, Zeng Jing, Abulikemu Abudu Rexit. Highly Active Manganese Dioxide Catalyzed the Construction of S-S Bond[J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2483-2490.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Lin, Y. M.; Yi, W. B. Chin. J. Org. Chem. 2018, 38, 1207(in Chinese). (林雅玫, 易文斌, 有机化学, 2018, 38, 1207.)
[2] Gong, J. X.; Sheng, L.; Yao, L. G.; Li, J.; Zhou, Y. B.; Guo, Y. W. Chin. J. Org. Chem. 2012, 32, 593(in Chinese). (龚景旭, 盛丽, 姚励功, 李佳, 周宇波, 郭跃伟, 有机化学, 2012, 32, 593.)
[3] Su, W. K.; Liang, X. R.; Li, Y. S.; Zhang, Y. M. Chin. J. Org. Chem. 2003, 23, 1019(in Chinese). (梁现蕊, 李永曙, 张永敏, 苏为科, 有机化学, 2003, 23, 1019.)
[4] Gong, J, X.; Sun, Y, Q.; Wang, J, D.; Guo, Y, W. Chin. J. Org. Chem. 2008, 28, 252(in Chinese). (龚景旭, 孙艳秋, 王继栋, 郭跃伟, 有机化学, 2008, 28, 252.)
[5] Gong, J. J.; Shen, X.; Yao, L. G.; Jiang, H. L.; Krohn, K.; Guo, Y. W. Org. Lett. 2007, 9, 1715.
[6] Li, X. X.; Lin, S. F.; Chen, J. Nat. Prod. Res. Dev. 2012, 24, 132(in Chinese). (李新霞, 林守峰, 陈坚, 天然产物研究与开发, 2012, 24, 132.)
[7] Halai, R.; Craik, D. J. Nat. Prod. Rep. 2009, 26, 526.
[8] Lee, S. H. Arch. Pharm. Res. 2009, 32, 299.
[9] Wender, P. A.; Goun, E. A.; Jones, L. R.; Pillow, T. H.; Rothbard, J. B.; Shinde, S.; Contag, C. H. Proc. Nat.l Acad. Sci. U. S. A. 2007, 104, 10340.
[10] Maurela, F.; Debartb, F.; Cavelierc, F.; Thierrya, A. R..; Lebleu, B.; Vasseur, J. J.; Vives, E. Bioorg. Med. Chem. Lett. 2005, 15, 5084.
[11] Besret, S.; Ollivier, N.; Blanpain, A.; Melnyk, O. J. Pept. Sci. 2008, 14, 1244.
[12] Gottlieb, D.; Grunwald, C.; Nowak, C.; Kuhlmann, J.; Waldmann, H. Chem. Commun. 2006, 3, 260.
[13] Alexander, M.; Gerauer, M.; Pechlivanis, M.; Popkirova, B.; Dvorsky, R.; Brunsveld, L.; Waldmann, H.; Kuhlmann, J. ChemBioChem 2009, 10, 98.
[14] Dou, Y. C.; Huang, X.; Wang, H.; Yang, L. T.; Li, H.; Yuan, B. X.; Yang, G. Y. Green. Chem. 2017, 19, 2491.
[15] Gormer, K.; Waldmann, H.; Triola, G. J. Org. Chem. 2010, 75, 1811.
[16] Huang, P. F.; Wang, P.; Tang, S.; Fu, Z. J.; Lei, A. W. Angew. Chem., Int. Ed. 2018, 57, 8115.
[17] Stellenboom, N.; Hunter, R.; Caira, M. R. Tetrahedron 2010, 66, 3228.
[18] Yang, F.; Wang, W.; Li, K.; Zhao, W. L.; Dong, X. C. Tetrahedron Lett. 2017, 58, 218.
[19] Parida, A.; Choudhuri, K.; Mal, P. Chem. Asian. J. 2019, 14, 2579.
[20] Noureldin, N. A.; Caldwell, M.; Hendry, J.; Lee, D, G. Synthesis 1998, 1587.
[21] Shaabani, A.; Tavasoli-Rad, F.; Lee, D. G. Synth. Commun. 2011, 35, 571.
[22] Liu, S. P.; Qi, Z. J.; Zhang, Z.; Qian, B. Org. Lett. 2019, 21, 7722.
[23] Yang, Y.; Hasimujiang, B.; Rexit, A. A. Chin. J. Org. Chem. 2019, 39, 727(in Chinese). (杨莹, 哈斯木江·巴拉提, 阿布都热西提·阿布力克木, 有机化学, 2019, 39, 727.)
[24] Liu, S. Z.; Rexit, A. A. Chemistry Bulletin 2019, 82, 270(in Chinese). (刘世钊, 阿布都热西提·阿布力克木, 化学通报, 2019, 82, 270.)

原位产生二氧化锰催化构建S—S键

Highly Active Manganese Dioxide Catalyzed the Construction of S-S Bond

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 3

编辑推荐

相关统计

本文评价

[1]	邓桂胜,许百华,刘春玉. 由硅醚经脱保护-氧化-Wittig反应一锅法合成α,β-不饱和酯[J]. 有机化学, 2006, 26(9): 1295-1299.
[2]	张振业,金淑惠,梁晓梅,王志强,王道全. N-取代环十二酮缩氨基硫脲的氧化环合反应[J]. 有机化学, 2001, 21(3): 235-237.
[3]	管晓培,于永忠. 对苯醌-2,5-二羧酸酯的合成[J]. 有机化学, 1994, 14(1): 80-83.