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2021 , Vol. 41 >Issue 4: 1639 - 1645

DOI: https://doi.org/10.6023/cjoc202008032

研究论文

聚硒醚催化环己烯氧化制备1,2-环己二醇

  • 黄杰军 ,
  • 钱蓉蓉 ,
  • 王爽 ,
  • 曹洪恩
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  • a 扬州大学园艺与植物保护学院 江苏扬州 225009
    b 江苏旅游职业学院 江苏扬州 225127
    c 江苏扬农化工集团有限公司 江苏扬州 225009

收稿日期: 2020-08-18

  修回日期: 2020-09-26

  网络出版日期: 2020-12-19

基金资助

国家重点研发计划(2018YFD0200100); 江苏省高校优势学科建设工程资助项目

收起

Polyselenide-Catalyzed Cyclohexene Oxidation to Produce 1,2-Cyclohexanediol

  • Jiejun Huang ,
  • Rongrong Qian ,
  • Shuang Wang ,
  • Hong'en Cao
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  • a School of Horticulture and Plant Protection, Yangzhou University, Yangzhou, Jiangsu 225009
    b Jiangsu College of Tourism, Yangzhou, Jiangsu 225127
    c Jiangsu Yangnong Chemical Group Co. Ltd, Yangzhou, Jiangsu 225009
* Corresponding author. E-mail:

Received date: 2020-08-18

  Revised date: 2020-09-26

  Online published: 2020-12-19

Supported by

National Key Research and Development Program of China(2018YFD0200100); Priority Academic Program Development of Jiangsu Higher Education Institutions

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摘要

开发了一种一步合成聚硒醚的新方法, 该材料可用于催化环己烯二羟化合成重要的化工中间体环己二醇, 是一种高效并可回收的催化剂. 有趣的是, 该材料在分子层面的独特结构, 使得相关反应以自由基机理进行, 并可使用分子氧作为部分氧化剂, 这与之前许多报道的硒催化反应有所不同.

关键词： 硒; 聚硒醚; 环己烯; 1,2-环己二醇; 绿色氧化

本文引用格式

黄杰军 , 钱蓉蓉 , 王爽 , 曹洪恩 . 聚硒醚催化环己烯氧化制备1,2-环己二醇[J]. 有机化学, 2021 , 41(4) : 1639 -1645 . DOI: 10.6023/cjoc202008032

Abstract

A new method for one-step synthesis of polyselenide was developed. The material was found to be an efficient and recyclable catalyst for the dihydroxylation of cyclohexene to produce 1,2-cyclohexanediol, which was an important inter- mediate for the synthesis of many fine chemicals. Interestingly, the unique structure of the catalyst at molecular level resulted in a novel free-radical reaction methanism allowing the utilization of O2 as the supplementary oxidant, which was quite different from most of the reported organoselenium-catalyzed reactions.

Key words： selenium; polyselenide; cyclohexene; 1,2-cyclohexanediol; green oxidation

参考文献

[1]
(a) Chen, Y.; Deng, X.; Jing, X.; Zhou, H. Chin. J. Org. Chem. 2020, 40,4147. (in Chinese)
[1]
( 陈颖, 邓鑫, 景崤壁, 周宏伟, 有机化学,2020, 40,4147.)
[1]
(b) Ge, Y.; Kong, J.; Yang, C.; Yang, Q.; Zhang, X. Chin. J. Org. Chem. 2020, 40,1760. (in Chinese)
[1]
( 葛颜玉, 孔晶, 杨成根, 杨倩, 张旭, 有机化学,2020, 40,1760.)
[1]
(c) Bao, W.-H.; He, M.; Wang, J.-T.; Peng, X.; Sung, M.; Tang, Z.; Jiang, S.; Cao, Z.; He, W.-M. J. Org. Chem. 2019, 84,6065.
[1]
(d) Lu, L.-H.; Wang, Z.; Xia, W.; Cheng, P.; Zhang, B.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2019, 30,1237.
[1]
(e) Higashimae, S.; Kurata, D.; Kawaguchi, S.-I.; Kodama, S.; Sonoda, M.; Nomoto, A.; Ogawa, A. J. Org. Chem. 2018, 83,5267.
[2]
(a) Ruberte, A.C.; Sanmartin, C.; Aydillo, C.; Sharma, A.K.; Plano, D. J. Med. Chem. 2020, 63,1473.
[2]
(b) Cao, H.; Yang, Y.; Chen, X.; Liu, J.; Chen, C.; Yuan, S.; Yu, L. Chin. Chem. Lett. 2020, 31,1887.
[2]
(c) Mao, X.; Li, P.; Li, T.; Zhao, M.; Chen, C.; Liu, J.; Wang, Z.; Yu, L. Chin. Chem. Lett. 2020, 31,3276.
[3]
(a) Wu, C.; Xiao, H.-J.; Wang, S.-W.; Tang, M.-S.; Tang, Z.-L.; Xia, W.; Li, W.-F.; Cao, Z.; He, W.-M. ACS Sustainable Chem. Eng. 2019, 7,2169.
[3]
(b) Goulart, T.A. C.; Kazmirski, J.A. G.; Back, D.F.; Zeni, G. J. Org. Chem. 2019, 84,14113.
[3]
(c) Liu, M.-X.; Li, Y.-M.; Yu, L.; Xu, Q.; Jiang, X.-F. Sci. China: Chem. 2018, 61,294.
[4]
(a) Chen, X.; Mao, J.; Liu, C.; Chen, C.; Cao, H.; Yu, L. Chin. Chem. Lett. 2020, 31,3205.
[4]
(b) Zhu, Z.; Wang, W.; Zeng, L.; Zhang, F.; Liu, J. Catal. Commun. 2020, 142,106031.
[4]
(c) Cao, K.-H.; Deng, X.; Chen, T.; Zhang, Q.-T.; Yu, L. J. Mater. Chem. A 2019, 7,10918.
[5]
Singh, F.V.; Wirth, T. Catal. Sci. Technol. 2019, 9,1073.
[6]
(a) Yu, L.; Cao, H.-E.; Zhang, X.; Chen, Y.; Yu, L. Sustainable Energy Fuels 2020, 4,730.
[6]
(b) Zheng, Y.-H.; Wu, A.-Q.; Ke, Y.-Y.; Cao, H.-E.; Yu, L. Chin. Chem. Lett. 2019, 30,937.
[6]
(c) Liu, X.; Liang, Y.-Y.; Ji, J.-Y.; Luo, J.; Zhao, X.-D. J. Am. Chem. Soc. 2018, 140,4782.
[6]
(d) Depken, C.; Kr?tzschmar, F.; Rieger, R.; Rode, K.; Breder, A. Angew. Chem., Int. Ed. 2018, 57,2459.
[6]
(e) Yu, L.; Chen, C. CN 106432739,2017.
[7]
Chen, C.; Cao, Y.-T.; Wu, X.-X; Cai, Y.-L.; Liu, J.; Xu, L.; Ding, K.-H.; Yu, L. Chin. Chem. Lett. 2020, 31,1078.
[8]
(a) Chen, Y.; Jing, X.; Yu, L. Chin. J. Org. Chem. 2020, 40,2570. (in Chinese)
[8]
( 陈颖, 景崤壁, 俞磊, 有机化学,2020, 40,2570.)
[8]
(b) Yang, Y.; Li, M.; Cao, H.; Zhang, X.; Yu, L. Mol. Catal. 2019, 474,110450.
[8]
(c) Zhao, S.-Y.; Xu, B.-L.; Yu, L.; Fan, Y.-N. Chin. Chem. Lett. 2018, 29,884.
[8]
(d) Zhao, S.-Y.; Xu, B.-L.; Yu, L.; Fan, Y.-N. Chin. Chem. Lett. 2018, 29,475.
[8]
(e) Fan, X.; Yi, R.; Wang, F.; Zhang, X.; Xu, Q.; Yu, L. Chin. J. Org. Chem. 2018, 38,2736. (in Chinese)
[8]
( 范昕, 易容, 王芳, 张旭, 徐清, 俞磊, 有机化学,2018, 38,2736.)
[8]
(f) Zhang, D.-L.; Wei, Z.; Yu, L. Sci. Bull. 2017, 62,1325.
[8]
(g) Tong, Q.; Gao, Q.; Xu, B.; Yu, L.; Fan, Y. Chin. J. Org. Chem. 2017, 37,753. (in Chinese)
[8]
( 仝庆, 高强, 许波连, 俞磊, 范以宁, 有机化学,2017, 37,753.)
[9]
Rayman, M. Lancet 2012, 379,1256.
[10]
Freudendahl, D.M.; Santoro, S.; Shahzad, S.A.; Santi, C.; Wirth, T. Angew. Chem., Int. Ed. 2009, 48,8409.
[11]
Cao, H.-E.; Zhu, B.-R.; Yang, Y.-F.; Xu, L.; Yu, L.; Xu, Q. Chin. J. Catal. 2018, 39 899 .
[12]
Yu, L.; Wang, J.; Chen, T.; Wang, Y.-G.; Xu, Q. Appl. Organomet. Chem. 2014, 28,652.
[13]
(a) Yu, L.; Qian, R.-R.; Deng, X.; Wang, F.; Xu, Q. Sci. Bull. 2018, 63,1010.
[13]
(b) Zhang, H.; Han, M.-T.; Yang, C.-G.; Yu, L.; Xu, Q. Chin. Chem. Lett. 2019, 30,263.
[14]
Santoro, S.; Santi, C.; Sabatini, M.; Testaferri, L.; Tiecco, M. Adv. Synth. Catal. 2008, 350,2881.
[15]
Yu, L.; Wang, J.; Chen, T.; Ding, K.-H.; Pan, Y. Chin. J. Org. Chem. 2013, 33,1096. (in Chinese)
[15]
( 俞磊, 王俊, 陈天, 丁克鸿, 潘毅, 有机化学,2013, 33,1096.)
[16]
Wang, Y.-G.; Yu, L.-H.; Zhu, B.-C.; Yu, L. J. Mater. Chem. A 2016, 4,10828.
[17]
Jing, X.; Yuan, D.; Yu, L. Adv. Synth. Catal. 2017, 359,1194.
[18]
(a) Yu, L.; Ye, J.-Q.; Zhang, X.; Ding, Y.-H.; Xu, Q. Catal. Sci. Technol. 2015, 5,4830.
[18]
(b) Zhang, X.; Ye, J.; Yu, L.; Shi, X.; Zhang, M.; Xu, Q.; Lautens, M. Adv. Synth. Catal. 2015, 357,955.
[19]
(a) Deng, X.; Cao, H.-E.; Chen, C.; Zhou, H.-W.; Yu, L. Sci. Bull. 2019, 64,1280.
[19]
(b) Deng, X.; Qian, R.; Zhou, W.; Yu, L. Chin. Chem. Lett. 2021, doi: 10.1016/j.cclet.2020.09.012.
[20]
Lee, C.-Y.; Kim, S.; Lee, K.-B.; Yoo, Y.-C.; Ryu, S.-Y.; Song, K.-S.; Arch. Pharm. Res. 2003, 26,367.
[21]
(a) Ribaudo, G.; Bellanda, M.; Menegazzo, I.; Wolters, L.P.; Bortoli, M.; Ferrer-Sueta, G.; Zagotto, G.; Orian, L. Chem.-Eur. J. 2017, 23,2405.
[21]
(b) Goodman, M.A.; Detty, M.R. Organometallics 2004, 23,3016.
[22]
Ou, W.; Zou, R.; Han, M.-T.; Yu, L.; Su, C.-L. Chin. Chem. Lett. 2020, 31,1899.
[23]
Ribaudo, G.; Bellanda, M.; Menegazzo, I.; Wolters, L.P.; Bortoli, M.; Ferrer-Sueta, G.; Zagotto, G.; Orian, L. Chem.-Eur. J. 2017, 23,2405.
[24]
(a) Cao, H.; Qian, R.; Yu, L. Catal. Sci. Technol. 2020, 10,3113.
[24]
(b) Liu, K.-J.; Deng, J.-H.; Yang, J.; Gong, S.-F.; Lin, Y.-W.; He, J.-Y.; Cao, Z.; He, W.-M. Green Chem. 2020, 22,433.
[24]
(c) Xie, L.-Y.; Fang, T.-G.; Tan, J.-X.; Zhang, B.; Cao, Z.; Yang, L.-H.; He, W.-M. Green Chem. 2019, 21,3858.
[25]
(a) Nacca, F.G.; Monti, B.; Lenard?o, E.J.; Evans, P.; Santi, C. Molecules 2020, 25,2018.
[25]
(b) Peng, S.; Lin, Y.; He, W. Chin. J. Org. Chem. 2020, 40,541. (in Chinese)
[25]
( 彭莎, 林英武, 何卫民, 有机化学,2020, 40,541.)
[25]
(c) He, W.-B.; Gao, L.-Q.; Chen, X.-J.; Wu, Z.-L.; Huang, Y.; Cao, Z.; Xu, X.-H.; He, W.-M. Chin. Chem. Lett. 2020, 31,1895.
[25]
(d) Xie, L.-Y.; Chen, Y.-L.; Qin, L.; Wen, Y.; Xie, J.-W.; Tan, J.-X.; Huang, Y.; Cao, Z.; He, W.-M. Org. Chem. Front. 2019, 6,3950.
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