SIOC English
有机化学
高级检索

有机化学 >

2023 , Vol. 43 >Issue 7: 2499 - 2505

DOI: https://doi.org/10.6023/cjoc202212008

研究论文

室温下酯与伯硫醇的硫酯化反应

  • 石义军 ,
  • 孙馨悦 ,
  • 曹晗 ,
  • 别福升 ,
  • 马杰 ,
  • 刘哲 ,
  • 丛兴顺
展开
  • a枣庄学院鲁南煤化工工程技术研究院 化学化工与材料科学学院 山东枣庄 277160
    b襄阳市公共检验检测中心 湖北襄阳 441000

收稿日期: 2022-12-06

  修回日期: 2023-01-28

  网络出版日期: 2023-02-23

基金资助

枣庄市科技发展计划(2018GH19); 山东省自然科学基金(ZR2019QB013)

收起

Thioesterification of Esters with Primary Aliphatic Thiols at Room Temperature

  • Yijun Shi ,
  • Xinyue Sun ,
  • Han Cao ,
  • Fusheng Bie ,
  • Jie Ma ,
  • Zhe Liu ,
  • Xingshun Cong
Expand
  • aEngineering and Technology Research Institute of Lunan Coal Chemical Engineering, College of Chemistry, Chemical Engineering and Materials Science, Zaozhuang University, Zaozhuang, Shandong 277160
    bXiangyang Public Inspection and Testing Center, Xiangyang, Hubei 441000
*E-mail: ;

Received date: 2022-12-06

  Revised date: 2023-01-28

  Online published: 2023-02-23

Supported by

Zaozhuang Science and Technology Development Program(2018GH19); Natural Science Foundation of Shandong Province(ZR2019QB013)

Fold

摘要

报道了在室温下酯与伯硫醇的硫酯化反应. 该方法的优点包括不使用过渡金属、条件温和、官能团耐受性良好、底物范围广泛及对脂肪醇酯和酚酯基团的优异化学选择性. 该方法成功地应用于丙磺舒硫酯的合成和顺序键的活化.

关键词： 硫酯化反应; 酯; 伯硫醇; 不使用过渡金属

本文引用格式

石义军 , 孙馨悦 , 曹晗 , 别福升 , 马杰 , 刘哲 , 丛兴顺 . 室温下酯与伯硫醇的硫酯化反应[J]. 有机化学, 2023 , 43(7) : 2499 -2505 . DOI: 10.6023/cjoc202212008

Abstract

The thioesterification of esters with primary aliphatic thiols at room temperature was reported. The advantages of the method include transition-metal-free, mild conditions, good functional group tolerance, broad substrate scope and excellent chemoselectivity with respect to aliphatic alcohol ester and phenolic ester groups. This method was successfully applied to the synthesis of probenecid thioester and sequential bond activation.

Key words： thioesterification; esters; primary aliphatic thiols; transition-metal-free

参考文献

[1]
(a) Suazo, K. F.; Park, K. Y.; Distefano, M. D. Chem. Rev. 2021, 121, 7178.
[1]
(b) Orrillo, A. G.; Furlan, R. L. E. Angew. Chem., Int. Ed. 2022, 61, e202201168.
[2]
(a) Hojo, H.; Takei, T.; Asahina, Y.; Okumura, N.; Takao, T.; So, M.; Suetake, I.; Sato, T.; Kawamoto, A.; Hirabayashi, Y. Angew. Chem., Int. Ed. 2021, 60, 13900.
[2]
(b) Chen, X.-L.; Wang, B.; Song, D.-P.; Pan, L.; Li, Y.-S. Macromolecules 2022, 55, 1153.
[2]
(c) Hernandez, J. J.; Dobson, A. L.; Carberry, B. J.; Kuenstler, A. S.; Shah, P. K.; Anseth, K. S.; White, T. J.; Bowman, C. N. Macromolecules 2022, 55, 1376.
[2]
(d) Zuo, C.; Ding, R.; Wu, X.; Wang, Y.; Chu, G.-C.; Liang, L.-J.; Ai, H.; Tong, Z.-B.; Mao, J.; Zheng, Q.; Wang, T.; Li, Z.; Liu, L.; Sun, D. Angew. Chem., Int. Ed. 2022, 61, e202201887.
[3]
(a) Roy, V. J.; Sen, P. P.; Raha Roy, S. J. Org. Chem. 2021, 86, 16965.
[3]
(b) Jha, R. K.; Upadhyay, A.; Kanika; Jain, S.; K, A. N.; Kumar, S. Org. Lett. 2022, 24, 7605.
[4]
(a) Feng, Y.; Yang, S.; Zhao, S.; Zhang, D. P.; Li, X.; Liu, H.; Dong, Y.; Sun, F. G. Org. Lett. 2020, 22, 6734.
[4]
(b) Zhu, Z.; Gong, Y.; Tong, W.; Xue, W.; Gong, H. Org. Lett. 2021, 23, 2158.
[4]
(c) Oyamada, Y.; Inaba, K.; Sasamori, T.; Nakamura, S. Chem. Commun. 2022, 58, 2172.
[5]
(a) Li, Y.; Bao, G.; Wu, X.-F. Chem. Sci. 2020, 11, 2187.
[5]
(b) Tian, Q.; Xu, S.; Zhang, C.; Liu, X.; Wu, X.; Li, Y. J. Org. Chem. 2021, 86, 8797.
[6]
(a) Xu, J. X.; Bao, Z. P.; Wu, X. F. Org. Lett. 2022, 24, 1848.
[6]
(b) Yano de Albuquerque, D.; Teixeira, W. K. O.; Sacramento, M. D.; Alves, D.; Santi, C.; Schwab, R. S. J. Org. Chem. 2022, 87, 595.
[7]
(a) Cellnik, T.; Healy, A. R. J. Org. Chem. 2022, 87, 6454.
[7]
(b) Huo, Y. W.; Qi, X.; Wu, X. F. Org. Lett. 2022, 24, 4009.
[7]
(c) Xu, R.-R.; Wang, W.; Qi, X.; Wu, X.-F. Org. Chem. Front. 2022, 9, 1417.
[8]
(a) Dong, J.; Yue, F.; Wang, X.; Song, H.; Liu, Y.; Wang, Q. Org. Lett. 2020, 22, 8272.
[8]
(b) Yan, J.; Tang, H.; Kuek, E. J. R.; Shi, X.; Liu, C.; Zhang, M.; Piper, J. L.; Duan, S.; Wu, J. Nat. Commun. 2021, 12, 7214.
[8]
(c) Xu, J. X.; Wang, L. C.; Wu, X. F. Org. Lett. 2022, 24, 4820.
[9]
Kim, Y.; Song, K. H.; Lee, S. Org. Chem. Front. 2020, 7, 2938.
[10]
(a) Xu, T.; Cao, T.; Yang, M.; Xu, R.; Nie, X.; Liao, S. Org. Lett. 2020, 22, 3692.
[10]
(b) Wang, Z.; Lin, X.; Chen, X.; Li, P.; Li, W. Org. Chem. Front. 2021, 8, 3469.
[10]
(c) Volkov, A. A.; Bugaenko, D. I.; Bogdanov, A. V.; Karchava, A. V. J. Org. Chem. 2022, 87, 8170.
[10]
(d) Ziyaei Halimehjani, A.; Breit, B. Chem. Commun. 2022, 58, 1704.
[11]
(a) Murakami, S.; Nanjo, T.; Takemoto, Y. Org. Lett. 2021, 23, 7650.
[11]
(b) Nemeth, A. G.; Szabo, R.; Nemeth, K.; Keseru, G. M.; Abranyi- Balogh, P. Org. Biomol. Chem. 2022, 20, 4361.
[12]
Qiao, Z.; Jiang, X. Org. Lett. 2016, 18, 1550.
[13]
Sundaravelu, N.; Nandy, A.; Sekar, G. Org. Lett. 2021, 23, 3115.
[14]
(a) Borgini, M.; Zamperini, C.; Poggialini, F.; Ferrante, L.; Summa, V.; Botta, M.; Fabio, R. D. ACS Med. Chem. Lett. 2020, 11, 846.
[14]
(b) Mavila, S.; Culver, H. R.; Anderson, A. J.; Prieto, T. R.; Bowman, C. N. Angew. Chem., Int. Ed. 2022, 61, e202110741.
[14]
(c) Sun, Y.-T.; Rao, X.; Xu, W.; Xu, M.-H. Org. Chem. Front. 2022, 9, 3467.
[15]
Jhawer, M.; Rosen, L.; Dancey, J.; Hochster, H.; Hamburg, S.; Tempero, M.; Clendeninn, N.; Mani, S. Invest. New Drugs 2007, 25, 85.
[16]
Tian, Q.; Sun, R.; Li, Y. Org. Biomol. Chem. 2022, 20, 1186.
[17]
Jiang, X.; Wang, G.; Zheng, Z.; Yu, X.; Hong, Y.; Xia, H.; Yu, C. Org. Lett. 2020, 22, 9762.
[18]
(a) Liu, X. S.; Tang, Z.; Li, Z.; Li, M.; Xu, L.; Liu, L. Nat. Commun. 2021, 12, 7298.
[18]
(b) Shen, L. W.; Zhang, Y. P.; You, Y.; Zhao, J. Q.; Wang, Z. H.; Yuan, W. C. J. Org. Chem. 2022, 87, 4232.
[18]
(c) Wu, Q.; Zhao, Y.-H.; Lu-Lu, C.; Li, H.-Y.; Li, H.-X. Org. Chem. Front. 2022, 9, 2977.
[19]
Sun, F.; Li, M.; He, C.; Wang, B.; Li, B.; Sui, X.; Gu, Z. J. Am. Chem. Soc. 2016, 138, 7456.
[20]
(a) Date, S.; Hamasaki, K.; Sunagawa, K.; Koyama, H.; Sebe, C.; Hiroya, K.; Shigehisa, H. ACS Catal. 2020, 10, 2039.
[20]
(b) Ahlemeyer, N. A.; Straub, M. R.; Leace, D. M.; Matz, B. A.; Birman, V. B. J. Org. Chem. 2021, 86, 1191.
[21]
(a) Bie, F.; Liu, X.; Cao, H.; Shi, Y.; Zhou, T.; Szostak, M.; Liu, C. Org. Lett. 2021, 23, 8098.
[21]
(b) Liu, C.; Szostak, M. Org. Chem. Front. 2021, 8, 4805.
[22]
(a) Liu, C.; Szostak, M. Chem. Commun. 2018, 54, 2130.
[22]
(b) Cao, H.; Liu, X.; Bie, F.; Shi, Y.; Han, Y.; Yan, P.; Szostak, M.; Liu, C. J. Org. Chem. 2021, 86, 10829.
[22]
(c) Cao, H.; Liu, X.; Bie, F.; Shi, Y.; Han, Y.; Yan, P.; Szostak, M.; Liu, C. Org. Chem. Front. 2021, 8, 1587.
[22]
(d) Zhou, J. Y.; Tian, R.; Zhu, Y. M. J. Org. Chem. 2021, 86, 12148.
[23]
(a) Kazemi, M.; Shiri, L. J. Sulfur Chem. 2015, 36, 613.
[23]
(b) Hirschbeck, V.; Gehrtz, P. H.; Fleischer, I. Chem.-Eur. J. 2018, 24, 7092.
[24]
(a) Brigham, C. E.; Malapit, C. A.; Lalloo, N.; Sanford, M. S. ACS Catal. 2020, 10, 8315.
[24]
(b) Liu, T.; Zhang, X.; Peng, Z.; Zhao, J. Green Chem. 2021, 23, 9916.
[24]
(c) Iimura, S.; Manabe, K.; Kobayashi, S. Chem. Commun. 2002, 1, 94.
[25]
(a) Luo, J.; Rauch, M.; Avram, L.; Diskin-Posner, Y.; Shmul, G.; Ben-David, Y.; Milstein, D. Nat. Catal. 2020, 3, 887.
[25]
(b) Park, S. J.; Hwang, I. S.; Chang, Y. J.; Song, C. E. J. Am. Chem. Soc. 2021, 143, 2552.
[25]
(c) Rauch, M.; Luo, J.; Avram, L.; Ben-David, Y.; Milstein, D. ACS Catal. 2021, 11, 2795.
[26]
(a) Hirschbeck, V.; Gehrtz, P. H.; Fleischer, I. J. Am. Chem. Soc. 2016, 138, 16794.
[26]
(b) Wang, X.; Wang, B.; Yin, X.; Yu, W.; Liao, Y.; Ye, J.; Wang, M.; Hu, L.; Liao, J. Angew. Chem., Int. Ed. 2019, 58, 12264.
[26]
(c) Ai, H.-J.; Lu, W.; Wu, X.-F. Angew. Chem., Int. Ed. 2021, 60, 17178.
[26]
(d) Ai, H.-J.; Zhao, F.; Geng, H.-Q.; Wu, X.-F. ACS Catal. 2021, 11, 3614.
[27]
(a) Li, G.; Szostak, M. Nat. Commun. 2018, 9, 4165.
[27]
(b) Wang, Q.; Liu, L.; Dong, J.; Tian, Z.; Chen, T. New J. Chem. 2019, 43, 9384.
[27]
(c) Kuciński, K.; Hreczycho, G. Org. Process Res. Dev. 2018, 22, 489.
[27]
(d) Contente, M. L.; Roura Padrosa, D.; Molinari, F.; Paradisi, F. Nat. Catal. 2020, 3, 1020.
[27]
(e) Rahman, M. M.; Li, G.; Szostak, M. Synthesis 2020, 52, 1060.
[27]
(f) Shi, Y.; Liu, X.; Cao, H.; Bie, F.; Han, Y.; Yan, P.; Szostak, R.; Szostak, M.; Liu, C. Org. Biomol. Chem. 2021, 19, 2991.
[28]
Niwa, E.; Aoki, H.; Tanaka, H.; Tamura, T. Y.; Pang, J. H.; Wata- nabe, K.; Takita, R.; Chiba, S. Nippon Nogei Kagaku Kaishi 1967, 41, 135.
[29]
Yi, C.-L.; Huang, Y.-T.; Lee, C.-F. Green Chem. 2013, 15, 2476.
[30]
Maruani, A.; Lee, M. T. W.; Watkins, G.; Akhbar, A. R.; Baggs, H.; Shamsabadi, A.; Richards, D. A.; Chudasama, V. RSC Adv. 2016, 6, 3372.
[31]
Nyquist, R. A.; Potts, W. J. Spectrochim. Acta 1959, 15, 514.
[32]
Zeng, J.-W.; Liu, Y.-C.; Hsieh, P.-A.; Huang, Y.-T.; Yi, C.-L.; Badsara, S. S.; Lee, C.-F. Green Chem. 2014, 16, 2644.
[33]
Samanta, R. C.; De Sarkar, S.; Fr?hlich, R.; Grimme, S.; Studer, A. Chem. Sci. 2013, 4, 2177.
Options
文章导航

/

〈 〉