SIOC English
有机化学
高级检索

有机化学 >

2021 , Vol. 41 >Issue 9: 3726 - 3732

DOI: https://doi.org/10.6023/cjoc202102024

研究简报

电化学氧化-碘促进丙酮α-H芳(烷)硒化制备α-芳(烷)硒基丙酮

  • 易荣楠 ,
  • 刘冬娴 ,
  • 吴啟林 ,
  • 赵明明 ,
  • 王勇 ,
  • 王峥
展开
  • a 湖南警察学院刑事科学技术系 长沙 410138
    b 中南大学基础医学院 法医学系 长沙 410013
    c 湖南科技学院化学与生物工程学院 湖南永州 425100
    d 长江师范学院化学化工学院 重庆 408000

收稿日期: 2021-02-08

  修回日期: 2021-03-20

  网络出版日期: 2021-06-08

基金资助

湖南省自然科学基金(2019JJ40392); 湖南省自然科学基金(2019JJ50193)

收起

Electrochemical Oxidated-Iodide Promoted α-H Aryl(alkyl)selenation of Acetone for the Preparation of α-Aryl(alkyl)selenoacetones

  • Rongnan Yi ,
  • Dongxian Liu ,
  • Qilin Wu ,
  • Mingming Zhao ,
  • Yong Wang ,
  • Zheng Wang
Expand
  • a Criminal Technology Department, Hunan Police Academy, Changsha 410138
    b Department of Forensic Science, School of Basic Medical Science, Central South University, Changsha 410013
    c Department of Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan 425100
    d Department of Chemistry and Chemical Engineering, Yangtze Normal University, Chongqing 408000
* Corresponding authors. E-mail: ;

Received date: 2021-02-08

  Revised date: 2021-03-20

  Online published: 2021-06-08

Supported by

Natural Science Foundation of Hunan Province(2019JJ40392); Natural Science Foundation of Hunan Province(2019JJ50193)

Fold

摘要

α-芳(烷)硒基酮作为重要的中间体在有机合成方面具有重要的应用. 报道了电化学氧化-碘促进下, 丙酮α-H芳(烷)硒化制备α-芳(烷)硒基丙酮化合物的方法, 本方法使用稳定、易得的二芳(烷)基二硒醚作为硒化试剂. 与已有的其它方法相比, 本方法具有反应条件温和、原子经济性高、底物适用范围广等优点, 为α-芳(烷)硒基丙酮化合物的制备提供了一条绿色、高效的合成路径.

关键词： 有机电合成; 碘促进反应; α-H芳(烷)硒化; α-芳(烷)硒基丙酮

本文引用格式

易荣楠 , 刘冬娴 , 吴啟林 , 赵明明 , 王勇 , 王峥 . 电化学氧化-碘促进丙酮α-H芳(烷)硒化制备α-芳(烷)硒基丙酮[J]. 有机化学, 2021 , 41(9) : 3726 -3732 . DOI: 10.6023/cjoc202102024

Abstract

α-Aryl(alkyl)selenyl ketones have been important intermediates in organic transformation. Here, a new route to α-aryl (alkyl) selenoacetones via the electrochemical oxidated iodide promoted α-H aryl(alkyl)selenation of acetone by using stable and easy available diaryl(alkyl)diselenides as selenide reagent is reported. Comparing to the previous methods, this strategy has the advantages of mild reaction conditions, high atom economy and wide functional groups tolerance, providing an efficient and green route to α-aryl (alkyl) selenoacetones.

Key words： electro-organic synthesis; iodide-promoted reaction; α-H aryl(alkyl)selenation; α-aryl(alkyl)selenoacetones

参考文献

[1]
Kolonko, K. J.; Wherritt, D. J.; Reich, H. J. J. Am. Chem. Soc. 2011, 133, 16774.
[2]
Mukherjee, A. J.; Zade, S. S.; Singh, H. B.; Sunoj, R. B. Chem. Rev. 2010, 110, 4357.
[3]
Mugesh, G.; du Mont, W. W.; Sies, H. Chem. Rev. 2001, 101, 2125.
[4]
Chen, J. Y.; Wu, H. Y.; Gui, Q. W.; Yan, S. S.; Deng, J.; Lin, Y. W.; Cao, Z.; He, W. M. Chin. J. Catal. 2021, 42, 1445.
[5]
Nian, H.; Bisson, W. H.; Dashwood, W.-M.; Pinto, J. T.; Dashwood, R. H. Carcinogenesis 2009, 30, 1416.
[6]
Chen, Z.; Lai, H.; Hou, L.; Chen, T. Chem. Commun. 2020, 56, 179.
[7]
Mukherjee, A. J.; Zade, S. S.; Singh, H. B.; Sunoj, R. B. Chem. Rev. 2010, 110, 4357.
[8]
Doering, M.; Ba, L. A.; Lilienthal, N.; Nicco, C.; Scherer, C.; Abbas, M.; Zada, A. A. P.; Coriat, R.; Burkholz, T.; Wessjohann, L.; Diederich, M.; Batteux, F.; Herling, M.; Jacob, C. J. Med. Chem. 2010, 53, 6954.
[9]
Dunlap, T. L.; Howell, C. E.; Mukand, N.; Chen, S. N.; Pauli, G. F.; Dietz, B. M.; Bolton, J. L. Chem. Res. Toxicol. 2017, 30, 2084.
[10]
Guo, P.; Wang, Q.; Liu, J.; Liu, L.; Zhao, P.; Cao, Y.; Liu, Y.; Qi, C. Biol. Trace Elem. Res. 2013, 154, 304.
[11]
Yu, Y.; Jin, Y.; Zhou, J.; Ruan, H.; Zhao, H.; Lu, S.; Zhang, Y.; Li, D.; Ji, X.; Ruan, B. H. ACS Chem. Biol. 2017, 12, 3003.
[12]
Desai, D.; Salli, U.; Vrana, K. E.; Amin, S. Bioorg. Med. Chem. Lett. 2010, 20, 2044.
[13]
Pinto, J. T.; Sinha, R.; Papp, K.; Facompre, N. D.; Desai, D.; El-Bayoumy, K. Int. J. Cancer 2007, 120, 1410.
[14]
Liao, L.; Guo, R.; Zhao, X. Angew. Chem. Int. Ed. 2017, 129, 3201.
[15]
Zeni, G.; Alves, D.; Pena, J. M.; Braga, A. L.; Stefani, H. A.; Nogueira, C. W. Org. Biomol. Chem. 2004, 35, 803.
[16]
Sharma, S.; Pathare, R. S.; Maurya, A. K.; Gopal, K.; Roy, T. K.; Sawant, D. M.; Pardasani, R. T. Org. Lett. 2016, 47, 356.
[17]
Wang, Y.; Yu, L.; Zhu, B.; Yu, L.; J. Mater. Chem. A 2016, 4, 10828.
[18]
Pandaa, S.; Pandaa, A.; Zade, S. S. Coord. Chem. Rev. 2015, 300, 86.
[19]
Yang, D.; Gao, Q.; Zheng, B. F.; Zhu, N. Y. J. Org. Chem. 2004, 69, 8821.
[20]
Pandey, G.; Tiwari, S. K.; Budakoti, A.; Sahani, P. K. Org. Chem. Front. 2018, 5, 2610.
[21]
Temperinia, A.; Siciliano, C. Tetrahedron 2020, 76, 131311.
[22]
Attanasi, O. A.; De Crescentini, L.; Mantellinia, F.; Marinib, F.; Nicolinia, S.; Sternativob, S.; Tiecco, M. Synlett 2009, 1118.
[23]
Yan, G.; Borah, A. J.; Wang, Li.; Pan, Z.; Chen, S.; Shen, X.; Wu, X. Tetrahedron Lett. 2015, 56, 4305.
[24]
Ouyang, Y.; Guo, C.; Qiu, R.; Li, N.; Chen, J.; Xu, X. Chin. J. Org. Chem. 2015, 35, 731. (in Chinese).
[24]
( 欧阳跃军, 郭翠霞, 邱仁华, 李宁波, 陈锦杨, 许新华, 有机化学, 2015, 35, 731.)
[25]
Wang, J.; Li, H.; Mei, Y.; Lou, B.; Xu, D;. Xie, D.; Guo, H.; Wang, W. J. Org. Chem. 2005, 70, 5678.
[26]
Victoria, F. N.; Radatz, C. S.; Sachini, M.; Jacob, R. G.; Perin, G.; da Silva, W. P.; Lenardão, E. J. Tetrahedron Lett. 2009, 50, 6761.
[27]
Wang, J.; Li, H.; Mei, Y.; Lou, B.; Xu, D.; Xie, D.; Guo, H.; Wang, W. J. Org. Chem. 2005, 70, 5678.
[28]
Yang, M. H.; Wang, H. S.; Zheng, Y. F.; Zhu, C. J. Chin. J. Org. Chem. 2006, 26, 1268. (in Chinese).
[28]
( 杨明华, 王红松, 郑云法, 朱成建, 有机化学, 2006, 26, 1268.)
[29]
Yang, X. Y.; Wang, R.; Wang, L.; Li, J.; Mao, S.; Zhang, S. Q.; Chen, N. RSC Adv. 2020, 10, 28902.
[30]
Movassagh, M. N. Tetrahedron Lett. 2009, 50, 1453.
[31]
Tang, S.; Liu, Y.; Lei, A. Chem 2018, 4, 27.
[32]
Shi, S.-H.; Liang, Y.; Jiao, N. Chem. Rev. 2020, 121, 485.
[33]
Kingston, C.; Palkowitz, M. D.; Takahira, Y.; Vantourout, J. C.; Peters, B. K.; Kawamata, Y.; Baran, P. S. Acc. Chem. Res. 2020, 53, 72.
[34]
Zhou, Y.; Zhao, Z.; Zeng, L.; Li, M.; He, Y.; Gu, L. Chin. J. Org. Chem. 2021, 41, 1072. (in Chinese).
[34]
( 周娅琴, 赵志恒, 曾亮, 李鸣, 何永辉, 谷利军, 有机化学, 2020 41, 1072.)
[35]
Zeng, L.; Li, J.; Gao, J.; Huang, X.; Wang, W.; Zheng, X.; Gu, L.; Li, G.; Zhang, S.; He, Y. Green Chem. 2020, 22, 3416.
[36]
Zhao, Z.; Li, M.; Zhou, Y.; He, Y.; Zhang, L.; Li, G.; Gu, L. Chin. J. Org. Chem. 2020, 41, 2476. (in Chinese).
[36]
( 赵志恒, 李鸣, 周娅琴, 何永辉, 张丽珠, 李干鹏, 谷利军, 有机化学, 2020, 41, 2476.)
[37]
Zuo, H.-D.; Hao, W.-J.; Zhu, C.-F.; Guo, C.; Tu, S.-J.; Jiang, B. Org. Lett. 2020, 22, 4471.
[38]
Jiang, J.; Wang, Z.; He, W. M. Chin. Chem. Lett. 2021, 32, 1591.
[39]
Wang, X. Y.; Xu, X. T.; Wang, Z. H.; Fang, P.; Mei, T. S. Chin. J. Org. Chem. 2020, 40, 3738. (in Chinese).
[39]
( 王向阳, 徐学涛, 王振华, 方萍, 梅天胜, 有机化学, 2020, 40, 3738.)
[40]
Xu, P.; Chen, P. Y.; Xu, H. C. Angew. Chem. Int. Ed. 2020, 59, 14275.
[41]
Chen, J. Y.; Wu, H. Y.; Gui, Q. W.; Han, X. R.; Wu, Y.; He, W. M. Org. Lett. 2020, 22, 2206.
[42]
Cao, Z. C.; Liu, J. C.; Chu, Y. Q.; Zhao, F. M.; Zhu, Y. H.; She, Y. B. Chin. J. Org. Chem. 2019, 39, 2499. (in Chinese).
[42]
( 曹志成, 刘建超, 褚有群, 赵峰鸣, 朱英红, 佘远斌, 有机化学, 2019, 39, 2499.)
[43]
Pan, C.; Liu, P.; Wu, A. G.; Li, M.; Wen, L. R.; Guo, W. S. Chin. J. Org. Chem. 2020, 40, 2855. (in Chinese).
[43]
( 潘超, 刘鹏, 武安国, 李明, 文丽荣, 郭维斯, 有机化学, 2020, 40, 2855.)
[44]
Li, M. F.; Wang, R.; Hao, W. J.; Jiang, B. Chin. J. Org. Chem. 2020, 40, 1540. (in Chinese).
[44]
( 李梦帆, 王榕, 郝文娟, 姜波, 有机化学, 2020, 40, 1540.)
[45]
Chen, J. Y.; Zhong, C. T.; Gui, Q. W.; Zhou, Y. M.; Fang, Y. Y.; Liu, K. J.; Lin, Y. W.; Cao, Z.; He, W. M. Chin. Chem. Lett. 2021, 32, 475.
[46]
Leng, T.; Wu, G.; Zhou, Y. B.; Gao, W.; Ding, J.; Huang, X.; Liu, M.; Wu, H. Adv. Synth. Catal. 2018, 360, 4336.
Options
文章导航

/

〈 〉