综述与进展

氧气引发的硫中心自由基参与的构建S—S、P—S和C—S键研究进展

  • 赵喜 ,
  • 区颖聪 ,
  • 刘艳 ,
  • Keiji Maruoka ,
  • 陈迁
展开
  • a 广东工业大学轻工化工学院 广州 510006
    b 京都大学药学院 京都 606-8501 日本

收稿日期: 2021-05-10

  修回日期: 2021-06-08

  网络出版日期: 2021-07-06

基金资助

广东省科技计划(2021A0505030069); 广东工业大学青年百人计划(220413506)

Recent Progress in the Construction of S—S, P—S and C—S Bonds Involving O2-Initiated Sulfur-Centered Radicals

  • Xi Zhao ,
  • Yingcong Ou ,
  • Yan Liu ,
  • Keiji Maruoka ,
  • Qian Chen
Expand
  • a School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China
    b Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo, Kyoto 606-8501, Japan
* Corresponding author. E-mail:

Received date: 2021-05-10

  Revised date: 2021-06-08

  Online published: 2021-07-06

Supported by

Science and Technology Planning Project of Guangdong Province(2021A0505030069); 100 Young Talents Program of Guangdong University of Technology(220413506)

摘要

含硫有机化合物广泛应用于有机合成、医药、农药和功能材料等领域中, 发展绿色、温和、高效的有机硫化合物的合成方法具有重要意义. 作为理想的绿色氧化剂, 氧气可直接引发一些含硫化合物为硫中心自由基, 其参与的反应为构建S—S、P—S和C—S键提供了新途径. 该方法可避免使用毒性试剂、过渡金属和强氧化剂等, 而且反应条件温和. 依据反应类型的不同, 对近年来氧气引发的硫中心自由基参与的构建S—S、P—S和C—S键研究进展进行介绍.

本文引用格式

赵喜 , 区颖聪 , 刘艳 , Keiji Maruoka , 陈迁 . 氧气引发的硫中心自由基参与的构建S—S、P—S和C—S键研究进展[J]. 有机化学, 2021 , 41(9) : 3366 -3378 . DOI: 10.6023/cjoc202105015

Abstract

Sulfur-containing organic compounds have been widely used in organic synthesis, pharmaceuticals, pesticides and functional materials. Thus, the development of green, mild and highly efficient methodologies for the synthesis of organosulfur compounds is of great importance. Some sulfur-containing compounds can be directly initiated by O2 as the ideal green oxidant to generate sulfur-centered radicals, and the corresponding radical reactions provide a novel approach to the construction of S—S, P—S and C—S bonds. These reactions can be performed under mild conditions without the use of toxic reagents, transition metals and strong oxidants. In this review, the recent progress in the construction of S—S, P—S and C—S bonds involving O2-initiated sulfur-centered radicals is introduced on the basis of different reaction types.

参考文献

[1]
(a) Liu, H.; Jiang, X. Chem.-Asian J. 2013, 8, 2546.
[1]
(b) Lee, C.-F.; Liu, Y.-C.; Badsara, S. S. Chem.-Asian J. 2014, 9, 706.
[1]
(c) Chauhan, P.; Mahajan, S.; Enders, D. Chem. Rev. 2014, 114, 8807.
[1]
(d) Zhang, L.; Niu, C.; Yang, X.; Qin, H.; Yang, J.; Wen, J.; Wang, H. Chin. J. Org. Chem. 2020, 40, 1117. (in Chinese).
[1]
( 张龙菲, 牛聪, 杨晓婷, 秦宏云, 杨建静, 文江伟, 王桦, 有机化学, 2020, 40, 1117.)
[1]
(e) Wang, B.; Zhou, Y.; Luo, S.; Luo, X.; Chen, W.; Yang, S.; Wang, Z. Chin. J. Org. Chem. 2021, 41, 171. (in Chinese).
[1]
( 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.)
[2]
(a) Lin, Y.-M.; Lu, G.-P.; Wang, R.-K.; Yi, W.-B. Org. Lett. 2017, 19, 1100.
[2]
(b) Qiu, G; Lai, L.; Cheng, J.; Wu, J. Chem. Commun. 2018, 54, 10405.
[2]
(c) Hu, J.; Huang, Y.; Xu, X.; Qing, F. Chin. J. Org. Chem. 2019, 39, 177. (in Chinese).
[2]
( 胡娟娟, 黄焰根, 徐修华, 卿凤翎, 有机化学, 2019, 39, 177.)
[2]
(d) Wang, J.-Y.; Ma, L.; Li, Y.; Wang, X.-S. Chin. J. Org. Chem. 2019, 39, 232. (in Chinese).
[2]
( 王建勇, 马岚, 李彦, 王细胜, 有机化学, 2019, 39, 232.)
[2]
(e) Guo, W.; Tao, K.; Tan, W.; Zhao, M.; Zheng, L.; Fan, X. Org. Chem. Front. 2019, 6, 2048.
[2]
(f) Chen, Z.; Zhang, H.; Zhou, S.; Cui, X. Chin. J. Org. Chem. 2020, 40, 3866. (in Chinese).
[2]
( 陈志超, 张红, 周树锋, 崔秀灵, 有机化学, 2020, 40, 3866.)
[2]
(g) Ghosh, A. K.; Mondal, S.; Hajra, A. Org. Lett. 2020, 22, 2771.
[2]
(h) Pramanik, M.; Choudhuri, K.; Mal, P. Org. Biomol. Chem. 2020, 18, 8771.
[2]
(i) Choudhuri, T.; Pramanik, M.; Mal, P. J. Org. Chem. 2020, 85, 11997.
[3]
(a) De?ne?s, F.; Schiesser, C. H.; Renaud, P. Chem. Soc. Rev. 2013, 42, 7900.
[3]
(b) De?ne?s, F.; Pichowicz, M.; Povie, G.; Renaud, P. Chem. Rev. 2014, 114, 2587.
[3]
(c) Pan, X.-Q.; Zou, J.-P.; Yi, W.-B.; Zhang, W. Tetrahedron 2015, 71, 7481.
[3]
(d) Yang, W.; Zhang, M.; Chen, W.; Yang, X.; Feng, J. Chin. J. Org. Chem. 2020, 40, 4060. (in Chinese).
[3]
( 杨文超, 张明明, 陈旺, 杨小虎, 冯建国, 有机化学, 2020, 40, 4060.)
[4]
(a) Shi, Z.; Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381.
[4]
(b) Xu, J.; Song, Q. Chin. J. Org. Chem. 2016, 36, 1151. (in Chinese).
[4]
( 许健, 宋秋玲, 有机化学, 2016, 36, 1151.)
[5]
(a) Chen, Q.; Huang, Y.; Wang, X.; Wu, J.; Yu, G. Org. Biomol. Chem. 2018, 16, 1713.
[5]
(b) Wen, C.; Wu, J.; Ou, Y.; Huang, Y.; Zhang, K.; Chen, Q. Tetrahedron Lett. 2018, 59, 3609.
[6]
Ruano, J. L. G.; Parra, A.; Alemán, J. Green Chem. 2008, 10, 706.
[7]
Liu, Y.; Wang, H.; Wang, C.; Wan, J.-P.; Wen, C. RSC Adv. 2013, 3, 21369.
[8]
Qiu, X.; Yang, X.; Zhang, Y.; Song, S.; Jiao, N. Org. Chem. Front. 2019, 6, 2220.
[9]
Song, S.; Zhang, Y.; Yeerlan, A.; Zhu, B.; Liu, J.; Jiao, N. Angew. Chem. Int. Ed. 2017, 56, 2487.
[10]
He, W.; Hou, X.; Li, X.; Song, L.; Yu, Q.; Wang, Z. Tetrahedron 2017, 73, 3133.
[11]
Wen, C.; Chen, Q.; Huang, Y.; Wang, X.; Yan, X.; Zeng, J.; Huo, Y.; Zhang, K. RSC Adv. 2017, 7, 45416.
[12]
Kharasch, M. S.; Nudenberg, W.; Mantell, G. J. J. Org. Chem. 1951, 16, 524.
[13]
Kamal, A.; Reddy, D. R.; Rajendar, J. Mol. Catal. A 2007, 272, 26.
[14]
Wang, H.; Lu, Q.; Qian, C.; Liu, C.; Liu, W.; Chen, K.; Lei, A. Angew. Chem. Int. Ed. 2016, 55, 1094.
[15]
Huo, C.; Wang, Y.; Yuan, Y.; Chen, F.; Tang, J. Chem. Commun. 2016, 52, 7233.
[16]
Wang, Y.; Jiang, W.; Huo, C. J. Org. Chem. 2017, 82, 10628.
[17]
Lu, Q.; Wang, H.; Peng, P.; Liu, C.; Huang, Z.; Luo, Y.; Lei, A. Org. Chem. Front. 2015, 2, 908.
[18]
Wang, H.; Wang, G.; Lu, Q.; Chiang, C.-W.; Peng, P.; Zhou, J.; Lei, A. Chem.-Eur. J. 2016, 22, 14489.
[19]
Lin, Y.-M.; Lu, G.-P.; Wang, R.-K.; Yi, W.-B. Org. Lett. 2016, 18, 6424.
[20]
Yu, G.; Ou, Y.; Chen, D.; Huang, Y.; Yan, Y.; Chen, Q. Synlett 2020, 31, 83.
[21]
Liu, Q.; Wang, L.; Yue, H.; Li, J.-S.; Luo, Z.; Wei, W. Green Chem. 2019, 21, 1609.
[22]
Chun, S.; Chung, J.; Park, J. E.; Chung, Y. K. ChemCatChem 2016, 8, 2476.
[23]
Choudhuri, K.; Mandal, A.; Mal, P. Chem. Commun. 2018, 54, 3759.
[24]
Liu, K.; Jia, F.; Xi, H.; Li, Y.; Zheng, X.; Guo, Q.; Shen, B.; Li, Z. Org. Lett. 2013, 15, 2026.
[25]
Sahoo, H.; Singh, S.; Baidya, M. Org. Lett. 2018, 20, 3678.
[26]
Lu, Q.; Zhang, J.; Wei, F.; Qi, Y.; Wang, H.; Liu, Z.; Lei, A. Angew. Chem. Int. Ed. 2013, 52, 7156.
[27]
Lu, Q.; Zhang, J.; Zhao, G.; Qi, Y.; Wang, H.; Lei, A. J. Am. Chem. Soc. 2013, 135, 11481.
[28]
Lu, Q.; Chen, J.; Liu, C.; Huang, Z.; Peng, P.; Wang, H.; Lei, A. RSC Adv. 2015, 5, 24494.
[29]
Shen, T.; Yuan, Y.; Song, S.; Jiao, N. Chem. Commun. 2014, 50, 4115.
[30]
Wei, W.; Liu, X.; Yang, D.; Dong, R.; Cui, Y.; Yuan, F.; Wang, H. Tetrahedron Lett. 2015, 56, 1808.
[31]
Liu, C.; Ding, L.; Guo, G.; Liu, W. Eur. J. Org. Chem. 2016, 2016, 910.
[32]
Liang, X.; Xiong, M.; Zhu, H.; Shen, K.; Pan, Y. J. Org. Chem. 2019, 84, 11210.
[33]
Liu, K.; Li, D.-P.; Zhou, S.-F.; Pan, X.-Q.; Shoberu, A.; Zou, J.-P. Tetrahedron 2015, 71, 4031.
[34]
Liao, Y.; Jiang, P.; Chen, S.; Xiao, F.; Deng, G.-J. RSC Adv. 2013, 3, 18605.
[35]
(a) Liu, X.; Cui, H.; Yang, D.; Dai, S.; Zhang, T.; Sun, J.; Wei, W.; Wang, H. RSC Adv. 2016, 6, 51830.
[35]
(b) Sun, P.; Yang, D.; Wei, W.; Jiang, L.; Wang, Y.; Dai, T.; Wang, H. Org. Chem. Front. 2017, 4, 1367.
[36]
Chen, Q.; Wang, X.; Wen, C.; Huang, Y.; Yan, X.; Zeng, J. RSC Adv. 2017, 7, 39758.
[37]
Jiang, Y.; Zou, J.-X.; Huang, L.-T.; Peng, X.; Deng, J.-D.; Zhu, L.-Q.; Yang, Y.-H.; Feng, Y.-Y.; Zhang, X.-Y.; Wang, Z. Org. Biomol. Chem. 2018, 16, 1641.
[38]
Chen, Q.; Huang, Y.; Wang, X.; Wen, C.; Yan, X.; Zeng, J. Tetrahedron Lett. 2017, 58, 3928.
[39]
Jiang, Y.; Deng, J.-d.; Wang, H.-h.; Zou, J.-x.; Wang, Y.-q.; Chen, J.-h.; Zhu, L.-q.; Zhang, H.-h.; Peng, X.; Wang, Z. Chem. Commun. 2018, 54, 802.
[40]
Zou, J.-X.; Wang, Y.-Q.; Huang, L.-T.; Jiang, Y.; Chen, J.-H.; Zhu, L.-Q.; Yang, Y.-H.; Feng, Y.-Y.; Peng, X.; Wang, Z. Org. Chem. Front. 2018, 5, 2317.
[41]
Chen, Q.; Yu, G.; Wang, X.; Huang, Y.; Yan, Y.; Huo, Y. Org. Biomol. Chem. 2018, 16, 4086.
[42]
Huang, L.-S.; Han, D.-Y.; Xu, D.-Z. Adv. Synth. Catal. 2019, 361, 4016.
[43]
Chen, Q.; Yu, G.; Wang, X.; Ou, Y.; Huo, Y. Green Chem. 2019, 21, 798.
文章导航

/

〈 〉