SIOC English
有机化学
高级检索

有机化学 >

2021 , Vol. 41 >Issue 12: 4749 - 4757

DOI: https://doi.org/10.6023/cjoc202109050

研究论文

亚磺酸钠盐和芳基乙酮/茚酮合成β-酮砜

  • 刘丽 ,
  • 肖洪 ,
  • 肖福红 ,
  • 谢艳军 ,
  • 黄华文 ,
  • 邓国军
展开
  • a 湘潭大学绿色有机合成与应用湖南省重点实验室 湖南湘潭 411105
    b 湖南工程学院环境催化与废弃物再生化湖南省重点实验室 湖南湘潭 411104
† 共同第一作者

收稿日期: 2021-09-30

  修回日期: 2021-11-05

  网络出版日期: 2021-11-10

基金资助

国家自然科学基金(21871226); 国家自然科学基金(21502160); 国家自然科学基金(21572194); 湖南省教育厅优秀青年(19B564)

收起

Synthesis of β-Ketosulfone from Sodium Sulfinate and Aryl Ethyl Ketone/Indanone

  • Li Liu ,
  • Hong Xiao ,
  • Fuhong Xiao ,
  • Yanjun Xie ,
  • Huawen Huang ,
  • Guojun Deng
Expand
  • a Hunan Key Laboratory of Green Organic Synthesis and Application, Xiangtan University, Xiangtan, Hunan 411105
    b Hunan Key Laboratory of Environmental Catalysis and Waste Rebiochemistry, Hunan Institute of Engineering, Xiangtan, Hunan 411104
† These authors contributed equally to this work.
* Corresponding authors. E-mail: ;

Received date: 2021-09-30

  Revised date: 2021-11-05

  Online published: 2021-11-10

Supported by

National Natural Science Foundation of China(21871226); National Natural Science Foundation of China(21502160); National Natural Science Foundation of China(21572194); Scientific Research Fund of Hunan Provincial Education Department(19B564)

Fold

摘要

报道了一类以亚磺酸钠盐和芳基乙酮/茚酮为原料, 在无金属条件下直接C—H键功能化制备β-酮砜的合成方法, 该方法操作步骤简便、反应条件温和, 同时具有良好的官能团兼容性. 该类反应实现了从C(sp3)—H直接到C—S键的构建, 从而避免了使用强氧化剂以及底物的预官能团化. 所得到的β-酮砜类化合物可以作为有机合成中间体进行转化.

关键词： 亚磺酸钠; β-酮砜化合物; C—H键功能化; C—S键; 无过渡金属

本文引用格式

刘丽 , 肖洪 , 肖福红 , 谢艳军 , 黄华文 , 邓国军 . 亚磺酸钠盐和芳基乙酮/茚酮合成β-酮砜[J]. 有机化学, 2021 , 41(12) : 4749 -4757 . DOI: 10.6023/cjoc202109050

Abstract

An efficient and convenient strategy for the preparation of β-ketosulfone via C—H bond functionalization with sodium sulfite and aryl ethyl ketone/indenone under metal-free condition has been reported. The method has simple operation steps, mild reaction conditions and good functional group compatibility. The reaction enables the direct formation of C(sp3)—H into C—S bonds, thereby avoiding the use of strong oxidants and prefunctionalization of substrates. The β-ketosulfone compounds can be transformed as intermediates in organic synthesis.

Key words： sodium sulfintes; β-keto sulfones; C—H functionalization; C—S bond; transition metal-free

参考文献

[1]
(a) Ahmad, I.; Shagufta, S. Int. J. Pharm. Pharm. Sci. 2015, 7, 19.
[1]
(b) Alba, A.-N. R.; Companyó, X.; Rios, R. Chem. Soc. Rev. 2010, 39, 2018.
[1]
(c) Meadows, D. C.; Gervay-Hague, J. Med. Res. Rev. 2006, 26, 793.
[1]
(d) Trost, B. M.; Kalnmals, C. A. Chem.-Eur. J. 2019, 25, 11193.
[2]
(a) Kupwade, R. V. J. Chem. Rev. 2019, 1, 99.
[2]
(b) Liu, N.-W.; Liang, S.; Manolikakes, G. Synthesis 2016, 48, 1939.
[3]
(a) Thomsen, M. W.; Handwerker, B. M.; Katz, S. A.; Belser, R. B. J. Org. Chem. 1988, 53, 906.
[3]
(b) Liu, K.; Ou, H.; Shi, X.; Dong, X.; Ma, W.; Wei, J. Chin. J. Org. Chem. 2014, 34, 681 (in Chinese.)
[3]
( 刘课艳, 偶辉, 石先莹, 董雪芬, 马文娟, 魏俊发, 有机化学, 2014, 34, 681.)
[4]
Vennstra, G. E.; Zwaneburg, B. Synthesis 1975, 519.
[5]
(a) Gund, S. H.; Shelkar, R. S.; Nagarkar, J. M. RSC Adv. 2015, 5, 62926.
[5]
(b) Zhang, K.; Xu, X. H.; Qing, F. L. J. Org. Chem. 2015, 80, 7658.
[5]
(c) Huang, F.; Batey, R. A. Tetrahedron 2007, 63, 7667.
[5]
(d) Yang, H.; Li, Y.; Jiang, M.; Wang, J.; Fu, H. Chem.-Eur. J. 2011, 17, 5652.
[5]
(e) Zhang, S.; Yang, S..; Huang, L.; Zhao, B.; Cheng, K.; Qi, C. Chin. J. Org. Chem. 2015, 35, 2259. (in Chinese)
[5]
( 张诗浓, 杨胜虎, 黄乐浩, 赵保丽, 程凯, 齐陈泽, 有机化学, 2015, 35, 2259.)
[6]
(a) Wang, Y.; Liu, Y. Acta Chim. Sinica 2019, 77, 418. (in Chinese)
[6]
( 王昱赟, 刘云云, 化学学报, 2019, 77, 418.)
[6]
(b) Tian, L.; Wan, J.-P.; Sheng, S. ChemCatChem. 2020, 12, 2533.
[6]
(c) Chen, Z.; Zhang, H.; Zhou, S.; Cui, X. Chin. J. Org. Chem. 2020, 40, 3866. (in Chinese)
[6]
( 陈志超, 张红, 周树锋, 崔秀灵, 有机化学, 2020, 40, 3866.)
[6]
(d) Guo, Y.; Wang, G.; Wei, L.; Wan, J.-P. J. Org. Chem. 2019, 84, 2984.
[6]
(e) Yu, Q.; Liu, Y.; Wan, J.-P. Chin. Chem. Lett. 2021, DOI: 10.1016/j.cclet.2021.04.037.
[7]
Reddy, R.-J.; Kumari, A.-H.; Kumar, J.-J. Org. Biomol. Chem. 2021, 19, 3087.
[8]
Samakkanad, N.; Katrun, P.; Techajaroonjit, T.; Hlekhlai, S; Pohmakotr, S.; Reutrakul, V.; Jaipetch, T.; Soorukram, D.; Kuhakarn, C. Synthesis 2012, 44, 1693.
[9]
Singh, A. K.; Chawla, R.; Yadav, L. D. S. Tetrahedron Lett. 2014, 55, 2845.
[10]
Chawla, R.; Singh A, K.; Yadav, L, D, S. Eur. J. Org. Chem. 2014, 10, 2032.
[11]
Singh, A. K.; Chawla, R.; Yadav, L, D, S. Tetrahedron Lett. 2014, 55, 4742.
[12]
Deng, S.; Liang, E.; Wu, Y.; Tang, X. Tetrahedron Lett. 2018, 59, 3955.
[13]
(a) Zhou, X.; Yu, R.; Wang, J.; Liao, X.; Xiong, Y.-S; Chin. J. Org. Chem. 2021, 41, 4370. (in Chinese)
[13]
( 周翔, 余茹鉴, 王金涛, 廖向文, 熊艳师, 有机化学, 2021, 41, 4370.)
[13]
(b) Wang, X.; Gao, J.; Xu, X.; Fang, Q.; Mei, T. Chin. J. Org. Chem. 2021, 41, 384. (in Chinese)
[13]
( 王向阳, 高君青, 徐学涛, 方萍, 梅天胜, 有机化学, 2021, 41, 384.)
[13]
(c) Jiang, L.; Li, Y.-G.; Li, H.; Yuan, M.; Chuan, Y.; Li, H.; Yuan, M.-L. J. Chem. Res. 2017, 41, 160.
[13]
(d) Huang, G.; Li, X.; Luo, J.; Luo, Z.; Tan, M. Chin. J. Org. Chem. 2019, 39, 617. (in Chinese)
[13]
( 黄国保, 李秀英, 罗金荣, 罗志辉, 谭明雄, 有机化学 2019, 39, 617.)
[13]
(e) Cheng, Z.; Zhang, H.; Zhou, S.; Cui, X. Chin. J. Org. Chem. 2020, 40, 3866. (in Chinese)
[13]
( 陈志超, 张红, 周树锋, 崔秀灵, 有机化学, 2020, 40, 3866.)
[13]
(f) Wang, B.; Zhou, Y.; Luo, S.; Luo, X.; Chen, W.; Yang, S.; Wang, C. Chin. J. Org. Chem. 2021, 41, 171. (in Chinese)
[13]
( 王柏文, 周永军, 罗时荷, 罗晓燕, 陈伟清, 杨诗敏, 汪朝阳, 有机化学, 2021, 41, 171.)
[14]
Xiao, F.; Cheng, H.; Xie, H.; Cheng, S.; Yang, L.; Deng, G.-J. Org. Lett. 2014, 16, 50.
[15]
Xiao, F.; Cheng, S.; Cheng, Y.; Huang, H.; Yang, L.; Deng, G.-J. Chem. Commun. 2015, 51, 652.
[16]
Xiao, F.; Chen, S.; Tian, J. X.; Huang, H.; Liu, Y.; Deng, G.-J. Green Chem. 2016, 18, 1538.
[17]
Xiao, F.; Liu, C.; Wang, D.; Huang, H.; Deng, G.-J. Green Chem. 2018, 20, 973.
[18]
Xiao, F.; Liu, C.; Yuan, S; Huang, H.; Liu, Y.; Deng, G.-J. J. Org. Chem. 2018, 83, 10420.
[19]
(a) Fu, L.; Xu, Z.; Wan, J.-P.; Liu, Y. Org. Lett. 2020, 22, 9518.
[19]
(b) Wan, J.-P.; Tu, Z.; Wang, Y. Chem.-Eur. J. 2019, 25, 6907.
[20]
Samanta, K.; Sarkar, R.; Bera, M. Tetrahedron Lett. 2021, 94, 132310.
[21]
Sahoo, A.; Dahiya, A.; Das, B.; Behera, A.; Patel, B. J. Org. Chem. 2021, 86, 11968.
[22]
Xiong, Y.-S.; Weng, J.; Lu, G. Adv. Synth. Catal. 2018, 360, 1611.
[23]
Ssa, Y.; Sina, S. Org. Lett. 2020, 22, 464.
[24]
Chen, J.; Allyson, Z. G.; Xin, J.-R.; Guan, Z.; He, Y.-H. Adv. Synth. Catal. 2018, 362, 2045.
[25]
Yang, J.; Li, H.; Li, M.; Peng, J.; Gu, Y. Adv. Synth. Catal. 2012, 354, 688.
Options
文章导航

/

〈 〉