SIOC English
有机化学
高级检索

有机化学 >

2021 , Vol. 41 >Issue 12: 4651 - 4660

DOI: https://doi.org/10.6023/cjoc202106006

综述与进展

光催化下二芳基碘鎓盐参与的自由基芳基化反应研究进展

  • 孙媛媛 ,
  • 宋敬城 ,
  • 秦启学 ,
  • 张恩选 ,
  • 韩晴晴 ,
  • 杨少慧 ,
  • 王祖利 ,
  • 岳姗 ,
  • 董道青
展开
  • a 青岛农业大学化学与药学院 山东青岛 266109
    b 凯莱英生命科学技术(天津)有限公司 天津 300457

收稿日期: 2021-06-03

  修回日期: 2021-07-03

  网络出版日期: 2021-07-26

基金资助

国家自然科学基金(21772107); 国家自然科学基金(21901010); 山东省重点研发计划(2019GSF108017)

收起

Recent Progress in Radical Arylation Reaction with Diaryliodonium Salts under Photocatalysis

  • Yuanyuan Sun ,
  • Jingcheng Song ,
  • Qixue Qin ,
  • Enxuan Zhang ,
  • Qingqing Han ,
  • Shaohui Yang ,
  • Zuli Wang ,
  • Shan Yue ,
  • Daoqing Dong
Expand
  • a College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao, Shandong 266109
    b Asymchem Life Science (Tianjin) Co. Ltd., Tianjin 300457
* Corresponding author. E-mail:

Received date: 2021-06-03

  Revised date: 2021-07-03

  Online published: 2021-07-26

Supported by

National Natural Science Foundation of China(21772107); National Natural Science Foundation of China(21901010); Key Research and Development Plan of Shandong Province(2019GSF108017)

Fold

摘要

二芳基高价碘盐在有机合成中被广泛应用. 总结了二芳基高价碘试剂在可见光诱导的自由基芳基化反应中的研究进展. 根据反应类型, 分为碳碳键的形成、碳硫键的形成和碳膦键的形成三部分进行综述.

关键词： 二芳基高价碘; 可见光; 自由基反应

本文引用格式

孙媛媛 , 宋敬城 , 秦启学 , 张恩选 , 韩晴晴 , 杨少慧 , 王祖利 , 岳姗 , 董道青 . 光催化下二芳基碘鎓盐参与的自由基芳基化反应研究进展[J]. 有机化学, 2021 , 41(12) : 4651 -4660 . DOI: 10.6023/cjoc202106006

Abstract

Diaryliodonium salts have been widely applied in organic transformations. According to the reaction type, the use of diaryliodonium salts in visible light induced arylation reactions is summarized from the following three parts: C—C bond formation, C—S bond formation and C—P bond formation.

Key words： diaryliodonium salt; visible light; radical reaction

参考文献

[1]
(a) Chen, J.; Qu, H. M.; Peng, J.; Chen, C. Chin. J. Org. Chem. 2015, 35, 937. (in Chinese)
[1]
( 陈静, 曲红梅, 彭静, 陈超, 有机化学, 2015, 35, 937.)
[1]
(b) Novák, Z.; Aradi, K.; Tóth, B.; Tolnai, G. Synlett 2016, 27, 1456.
[1]
(c) Ghosh, M. K.; Rout, N. ChemistrySelect 2020, 5, 13644.
[1]
(d) Chen, X.-J.; Gui, Q.-W.; Yi, R.; Yu, X.; Wu, Z.-L.; Huang, Y.; Cao, Z.; He, W.-M. Org. Biomol. Chem. 2020, 18, 5234.
[1]
(e) Takenaga, N.; Kumar, R.; Dohi, T. Front Chem. 2020, 8, 599026.
[2]
Xiong, B. Q.; Feng, X. F.; Zhu, L. Z.; Chen, T. Q.; Zhou, Y. B.; Au, C. T.; Yin, S. F. ACS Catal. 2015, 5, 537.
[3]
(a) Jalalian, N.; Petersen, T. B.; Olofsson, B. Chem.-Eur. J. 2012, 18, 14140.
[3]
(b) Shi, W. M.; Li, X. H.; Liang, C.; Mo, D. L. Adv. Synth. Catal. 2017, 359, 4129.
[4]
(a) Li, J.; Liu, L. RSC Adv. 2012, 2, 10485.
[4]
(b) Carroll, M. A.; Wood, R. A. Tetrahedron 2007, 63, 11349.
[4]
(c) Duan, W. Chin. J. Org. Chem. 2020, 40, 4387. (in Chinese)
[4]
( 段伟良, 有机化学, 2020, 40, 4387.)
[5]
(a) Dohi, T.; Ito, M.; Yamaoka, N.; Morimoto, K.; Fujioka, H.; Kita, Y. Angew. Chem., nt. Ed. 2010, 49, 3334.
[5]
(b) Li, H.; Yang, P.; Xu, Z.; Du, Z.; Fu, Y. Chin. J. Org. Chem. 2020, 40, 2476. (in Chinese)
[5]
( 李怀贵, 杨澎, 许峥, 杜正银, 傅颖, 有机化学, 2020, 40, 2476.)
[6]
(a) Umierski, N.; Manolikakes, G. Org. Lett. 2013, 15, 188.
[6]
(b) Zhu, K.; Song, Z.; Wang, Y.; Zhang, F. Org. Lett. 2020, 22, 9356.
[7]
(a) Wen, L. R.; Dou, Q.; Wang, Y. C.; Zhang, J. W.; Guo, W. S.; Li, M. J. Org. Chem. 2017, 82, 1428.
[7]
(b) Guo, W.; Li, S.; Tang, L.; Li, M.; Wen, L.; Chen, C. Org. Lett. 2015, 17, 1232.
[7]
(c) Wu, X.; Yang, Y.; Han, J.; Wang, L. Org. Lett. 2015, 17, 5654.
[7]
(d) Chen, Z.; Wang, W.-F.; Yang, H.; Wu, X.-F. Org. Lett. 2020, 22, 1980.
[8]
Sheng, J.; Wang, Y.; Su, X.; He, R.; Chen, C. Angew. Chem., nt. Ed. 2017, 56, 4824.
[9]
Wang, Y.; Chen, C.; Peng, J.; Li, M. Angew. Chem., nt. Ed. 2013, 52, 5323.
[10]
Shi, L.; Wang, Y.; Yang, H.; Fu, H. Org. Biomol. Chem. 2014, 12, 4070.
[11]
Wang, G.; Chen, C.; Peng, J. Chem. Commun. 2016, 52, 10277.
[12]
(a) Tang, G.; Li, X.; Xu, J.; Zhang, P.; Gao, Y.; Wu, J.; Zhao, Y. Synlett 2014, 25, 2009.
[12]
(b) Wang, L.; Han, J.; Yang, Y.; Wu, X.; Mao, S.; Yu, J. Synlett 2014, 25, 1419.
[12]
(c) Pan, C.; Wang, L.; Han, J. Org. Lett. 2020, 22, 4776.
[13]
(a) Ye, S. Q.; Li, X. F.; Xie, W. L.; Wu, J. Eur. J. Org. Chem. 2020, 2020, 1274.
[13]
(b) Guo, Y. Q.; Wang, R. G.; Song, H. J.; Liu, Y. X.; Wang, Q. M. Org. Lett. 2020, 22, 709.
[13]
(c) Krylov, I. B.; Lopat’eva, E. R.; Sub-botina, I. R.; Nikishin, G. I.; Yu, B.; Terent’ev, A. O. Chin. J. Catal. 2021, 42, 1700.
[13]
(d) Dong, D.; Sun, Y.; Li, G.; Yang, H.; Wang, Z.; Xu, X. Chin. J. Org. Chem. 2020, 40, 4071. (in Chinese)
[13]
( 董道青, 孙媛媛, 李光辉, 杨欢, 王祖利, 徐鑫明, 有机化学, 2020, 40, 4071.)
[13]
(e) Dong, D.-Q.; Yang, H.; Shi, J.-L.; Si, W.-J.; Wang, Z.-L.; Xu, X.-M. Org. Chem. Front. 2020, 7, 2538.
[14]
(a) Zhong, J. J.; Meng, Q. Y.; Chen, B.; Tung, C. H.; Wu, L. Z. Acta Chim. Sinica 2017, 75, 34. (in Chinese)
[14]
( 钟建基, 孟庆元, 陈彬, 佟振合, 吴骊珠, 化学学报, 2017, 75, 34.)
[14]
(b) Li, Z. L.; Jin, J.; Huang, S. H. Chin. J. Org. Chem. 2020, 40, 563. (in Chinese)
[14]
( 李祯龙, 金健, 黄莎华, 有机化学, 2020, 40, 563.)
[14]
(c) Kong, Y. L.; Xu, W. X.; Ye, F. X.; Weng, J. Q. Chin. J. Org. Chem. 2019, 39, 3065. (in Chinese)
[14]
( 孔瑶蕾, 徐雯秀, 叶飞霞, 翁建全, 有机化学, 2019, 39, 3065.)
[14]
(d) Guan, B. C.; Xu, X. L.; Wang, H.; Li, X. N. Chin. J. Org. Chem. 2016, 36, 1564. (in Chinese)
[14]
( 关保川, 许孝良, 王红, 李小年, 有机化学, 2016, 36, 1564.)
[14]
(e) Bagdi, A. K.; Rahman, M.; Bhattacherjee, D.; Zyryanov, G. V.; Ghosh, S.; Chupakhin, O. N.; Hajra, A. Green Chem. 2020, 22, 6632.
[14]
(f) Zhang, G. T.; Bian, C. L.; Lei, A. W. Chin. J. Catal. 2015, 36, 1428.
[14]
(g) Xie, L.-Y.; Liu, Y.-S.; Ding, H.-R.; Gong, S.-F.; Tan, J.-X.; He, J.-Y.; Cao, Z.; He, W.-M. Chin. J. Catal. 2020, 41, 1168.
[15]
(a) Meng, X. X.; Kang, Q. Q.; Zhang, J. Y.; Li, Q.; Wei, W. T.; He, W. M. Green Chem. 2020, 22, 1388.
[15]
(b) Liu, Y.; Chen, X. L.; Sun, K.; Li, X. Y.; Zeng, F. L.; Liu, X. C.; Qu, L. B.; Zhao, Y. F.; Yu, B. Org. Lett. 2019, 21, 4019.
[15]
(c) Davies, J.; Booth, S. G.; Essafi, S.; Dryfe, R. A. W.; Leonori, D. Angew. Chem., nt. Ed. 2015, 54, 14017.
[15]
(d) Zhang, Y.; Sun, K.; Lv, Q.; Chen, X.; Qu, L.; Yu, B. Chin. Chem. Lett. 2019, 30, 1361.
[15]
(e) 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.
[15]
(f) Yang, W.-C.; Chen, C.-Y.; Li, J.-F.; Wang, Z.-L. Chin. J. Catal. 2021, 42, 1865.
[16]
(a) Zhang, X.; Rakesh, K. P.; Ravindar, L.; Qin, H. L. Green Chem. 2018, 20, 4790.
[16]
(b) Lin, J. Q.; Han, Q.; Ding, Y. Chem. Rec. 2018, 18, 1531.
[16]
(c) He, S.; Chen, X.; Zeng, F.; Lu, P.; Peng, Y.; Qu, L.; Yu, B. Chin. Chem. Lett. 2020, 31, 1863.
[17]
(a) Zhou, W.; Jiang, Y.; Chen, L.; Liu, K.; Yu, D. Chin. J. Org. Chem. 2020, 40, 3697. (in Chinese)
[17]
( 周文俊, 蒋元旭, 陈亮, 刘开兴, 余达刚, 有机化学, 2020, 40, 3697.)
[17]
(b) Zhou, M. D.; Qin, P. T.; Jing, L. K.; Sun, J.; Du, H. W. Chin. J. Org. Chem. 2020, 40, 598. (in Chinese)
[17]
( 周明东, 覃丕涛, 经理珂, 孙京, 杜海武, 有机化学, 2020, 40, 598.)
[17]
(c) Peng, S.; Lin, Y. W.; He, W. M. Chin. J. Org. Chem. 2020, 40, 541. (in Chinese)
[17]
( 彭莎, 林英武, 何卫民, 有机化学, 2020, 40, 541.)
[17]
(d) Du, J. B.; Chen, Y. G.; Zuo, Z. W. Chin. J. Org. Chem. 2020, 40, 3646. (in Chinese)
[17]
( 杜建波, 陈跃刚, 左智伟, 有机化学, 2020, 40, 3646.)
[17]
(e) Chen, Y. F.; Zhao, H.; Cheng, D. P.; Li, X. N.; Xu, X. L. Chin. J. Org. Chem. 2020, 40, 1297. (in Chinese)
[17]
( 陈跃峰, 赵赫, 程冬萍, 李小年, 许孝良, 有机化学, 2020, 40, 1297.)
[17]
(f) Li, G.-H.; Han, Q.-Q.; Sun, Y.-Y.; Chen, D.-M.; Wang, Z.-L.; Xu, X.-M.; Yu, X.-Y. Chin. Chem. Lett. 2020, 31, 3255.
[17]
(g) Chen, D.; Sun, Y.; Dong, D.; Han, Q.; Wang, Z. Chin. J. Org. Chem. 2020, 40, 4267. (in Chinese)
[17]
( 陈德茂, 孙媛媛, 董道青, 韩晴晴, 王祖利, 有机化学, 2020, 40, 4267.)
[17]
(h) Meng, N.; Lv, Y.; Liu, Q.; Liu, R.; Zhao, X.; Wei, W. Chin. Chem. Lett. 2021, 32, 258.
[17]
(i) Gan, Z. Y.; Li, G. Q.; Yang, X. B.; Yan, Q. L.; Xu, G. Y.; Li, G. Y.; Jiang, Y. Y.; Yang, D. S. Sci. China: Chem. 2020, 63, 1652.
[17]
(j) Gui, Q.-W.; Teng, F.; Li, Z.-C.; Xiong, Z.-Y.; Jin, X.-F.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2021, 32, 1907.
[17]
(k) Jiang, T. G.; Wang, K.; Guo, T.; Wu, X. Y.; Zhang, G. K. Chin. J. Catal. 2020, 41, 161.
[17]
(l) Li, X. B.; Xiong, J.; Xu, Y.; Feng, Z. J.; Huang, J. T. Chin. J. Catal. 2019, 40, 424.
[17]
(m) Ren, D. D.; Shen, R. C.; Jiang, Z. M.; Lu, X. Y.; Li, X. Chin. J. Catal. 2020, 41, 31.
[17]
(n) Ren, Z. X.; Liu, X. J.; Zhuge, Z. H.; Gong, Y. Y.; Sun, C. Q. Chin. J. Catal. 2020, 41, 180.
[18]
Liu, Y.-X.; Xue, D.; Wang, J.-D.; Zhao, C.-J.; Zou, Q.-Z.; Wang, C.; Xiao, J. Synlett 2013, 24, 507.
[19]
Tobisu, M.; Furukawa, T.; Chatani, N. Chem. Lett. 2013, 42, 1203.
[20]
(a) Hu, H.; Hu, X.; Liu, Y. Angew. Chem., nt. Ed. 2020, 59, 18975.
[20]
(b) Yuan, Y.; Jiang, M.; Wang, T.; Xiong, Y.; Li, J.; Guo, H.; Lei, A. Chem. Commun. 2019, 55, 11091.
[20]
(c) Xie, L.-Y.; Peng, S.; Liu, F.; Liu, Y.-F.; Sun, M.; Tang, Z.-L.; Jiang, S.; Cao, Z.; He, W.-M. ACS Sustainable Chem. Eng. 2019, 7, 7193.
[20]
(d) Peng, S.; Song, Y.-X.; He, J.-Y.; Tang, S.-S.; Tan, J.-X.; Cao, Z.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2019, 30, 2287.
[20]
(e) Du, S.; Pi, C.; Wan, T.; Wu, Y.; Cui, X. Adv. Synth. Catal. 2019, 361, 1766.
[20]
(f) Dong, D. Q.; Li, L. X.; Li, G. H.; Deng, Q.; Wang, Z. L.; Long, S. Chin. J. Catal. 2019, 40, 1494.
[20]
(g) Yu, H.; Pi, C.; Wang, Y.; Cui, X.; Wu, Y. Chin. J. Org. Chem. 2018, 38, 124. (in Chinese)
[20]
( 余海洋, 皮超, 王勇, 崔秀灵, 吴养洁, 有机化学, 2018, 38, 124.)
[20]
(h) Xie, L.-Y.; Qu, J.; Peng, S.; Liu, K.-J.; Wang, Z.; Ding, M.-H.; Wang, Y.; Cao, Z.; He, W.-M. Green Chem. 2018, 20, 760.
[20]
(i) Yuan, J.-W.; Qu, L.-B. Chin. Chem. Lett. 2017, 28, 981.
[21]
Li, D. Z.; Liang, C.; Jiang, Z. X.; Zhang, J. Z.; Zhuo, W. T.; Zou, F. Y.; Wang, W. P.; Gao, G. L.; Song, J. Z. J. Org. Chem. 2020, 85, 2733.
[22]
Feng, J.; Li, B.; Jiang, J.; Zhang, M.; Ouyang, W.; Li, C.; Fu, Y.; Gu, Z. Chin. J. Chem. 2018, 36, 11.
[23]
Hopkinson, M. N.; Sahoo, B.; Glorius, F. Adv. Synth. Catal. 2014, 356, 2794.
[24]
Jiang, H.; Cheng, Y. Z.; Wang, R. Z.; Zhang, Y.; Yu, S. Y. Chem. Commun. 2014, 50, 6164.
[25]
Chen, Y.; Shu, C.; Luo, F.; Xiao, X.; Zhu, G. Chem. Commun. 2018, 54, 5373.
[26]
Mkrtchyan, S.; Iaroshenko, V. O. Chem. Commun. 2020, 56, 2606.
[27]
(a) Qiu, G.; Zhou, K.; Gao, L.; Wu, J. Org. Chem. Front. 2018, 5, 691.
[27]
(b) Qiu, G.; Lai, L.; Cheng, J.; Wu, J. Chem. Commun. 2018, 54, 10405.
[27]
(c) Li, G. H.; Dong, D. Q.; Deng, Q.; Yan, S. Q.; Wang, Z. L. Synthesis 2019, 51, 3313.
[27]
(d) Ni, B.; Zhang, B.; Han, J.; Peng, B.; Shan, Y.; Niu, T. Org. Lett. 2020, 22, 670.
[28]
Liu, N. W.; Liang, S.; Manolikakes, G. Adv. Synth. Catal. 2017, 359, 1308.
[29]
Nair, A. M.; Kumar, S.; Halder, I.; Volla, C. M. R. Org. Biomol. Chem. 2019, 17, 5897.
[30]
Breton-Patient, C.; Naud-Martin, D.; Mahuteau-Betzer, F.; Piguel, S. Eur. J. Org. Chem. 2020, 2020, 6653.
[31]
Li, Y.; Wang, M.; Jiang, X. ACS Catal. 2017, 7, 7587.
[32]
Sun, D. L.; Yin, K.; Zhang, R. H. Chem. Commun. 2018, 54, 1335.
[33]
Chen, Z.; Liu, N.-W.; Bolte, M.; Ren, H.; Manolikakes, G. Green Chem. 2018, 20, 3059.
[34]
Liu, N.-W.; Chen, Z.; Herbert, A.; Ren, H.; Manolikakes, G. Eur. J. Org. Chem. 2018, 2018, 5725.
[35]
(a) Gravel, E.; Poupon, E. Nat. Prod. Rep. 2010, 27, 32.
[35]
(b) Han, Y.; Zheng, H.; Zhang, Y. Y.; Yan, C. G. Chin. Chem. Lett. 2020, 31, 1337.
[35]
(c) Ye, Y. S.; Jiang, N. N.; Yang, X. W.; Xu, G. Chin. Chem. Lett. 2020, 31, 2433.
[35]
(d) Ma, X.; Luan, X. Chin. J. Org. Chem. 2020, 40, 1785. (in Chinese)
[35]
( 马小军, 栾新军, 有机化学, 2020, 40, 1785.)
[35]
(e) Nie, Q. Y.; Ji, Z. Y.; Tang, G. L. Chin. J. Org. Chem. 2020, 40, 3467. (in Chinese)
[35]
( 聂秋玥, 季珍瑜, 唐功利, 有机化学, 2020, 40, 3467.)
[35]
(f) Yang, M.; Cao, S. X.; He, Z. J. Chin. J. Org. Chem. 2019, 39, 2235. (in Chinese)
[35]
( 杨梅, 曹仕轩, 贺峥杰, 有机化学, 2019, 39, 2235.)
[35]
(g) Yue, Y. S.; Xie, Z. F.; Chu, Y. C.; Xue, S. S. Chin. J. Org. Chem. 2020, 40, 501. (in Chinese)
[35]
( 岳永双, 解正峰, 褚义成, 薛松松, 有机化学, 2020, 40, 501.)
[36]
Nair, A. M.; Halder, I.; Khan, S.; Volla, C. M. R. Adv. Synth. Catal. 2020, 362, 224.
[37]
Lecroq, W.; Bazille, P.; Morlet-Savary, F.; Breugst, M.; Lalevée, J.; Gaumont, A.-C.; Lakhdar, S. Org. Lett. 2018, 20, 4164.
[38]
Bugaenko, D. I.; Volkov, A. A.; Livantsov, M. V.; Yurovskaya, M. A.; Karchava, A. V. Chem.-Eur. J. 2019, 25, 12502.
Options
文章导航

/

〈 〉