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2022 , Vol. 42 >Issue 12: 3959 - 3978

DOI: https://doi.org/10.6023/cjoc202210013

综述与进展

基于芳基重氮盐的芳基自由基介导的不饱和键环化反应研究进展

  • 姜松 ,
  • 南宁 ,
  • 何景昊 ,
  • 郭嘉程 ,
  • 秦景灏 ,
  • 谢叶香 ,
  • 欧阳旋慧 ,
  • 宋仁杰
展开
  • a 江西省持久性污染物控制与资源循环利用重点实验室 南昌 330063
    b 化学生物传感与计量学国家重点实验室 长沙 410082
    c 江西省金属材料微结构调控重点实验室 南昌 330063
†共同第一作者

收稿日期: 2022-10-14

  修回日期: 2022-11-18

  网络出版日期: 2022-11-28

基金资助

国家自然科学基金(51878326); 国家自然科学基金(21861027); 国家自然科学基金(22161030); 国家自然科学基金(21901100); 江西省自然科学基金(20212ACB203007); 江西省自然科学基金(20204BCJ23010); 江西省自然科学基金(20202ACBL216017); 江西省自然科学基金(20212AEI91002); 江西省自然科学基金(20202ACB203002); 国家重点实验室专项课题经费(SKLCBSC-2021019)

收起

Recent Progress in Aryl Radical-Mediated Cyclization of Unsaturated Bonds Based on Aryldiazonium Salts

  • Song Jiang ,
  • Ning Nan ,
  • Jinghao He ,
  • Jiacheng Guo ,
  • Jinghao Qin ,
  • Yexiang Xie ,
  • Xuanhui Ouyang ,
  • Renjie Song
Expand
  • a Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang 330063
    b State Key Laboratory of Chemo/Biosensing and Chemometrics, Changsha 410082
    c Key Laboratory for Microstructural Control of Metallic Materials of Jiangxi Province, Nanchang 330063
†These authors contributed equally to this work.
*E-mail: ;
;

Received date: 2022-10-14

  Revised date: 2022-11-18

  Online published: 2022-11-28

Supported by

National Natural Science Foundation of China(51878326); National Natural Science Foundation of China(21861027); National Natural Science Foundation of China(22161030); National Natural Science Foundation of China(21901100); Natural Science Foundation of Jiangxi Province(20212ACB203007); Natural Science Foundation of Jiangxi Province(20204BCJ23010); Natural Science Foundation of Jiangxi Province(20202ACBL216017); Natural Science Foundation of Jiangxi Province(20212AEI91002); Natural Science Foundation of Jiangxi Province(20202ACB203002); Special Project Funds of State Key Laboratory(SKLCBSC-2021019)

Fold

摘要

芳基重氮盐以其较高的反应活性和广泛的来源, 被广泛应用于有机合成中. 芳基重氮盐作为一种常见的亲电试剂通过保留N2骨架和离去N2, 在材料化学、染料化学和药物化学等领域有着非常广泛的应用. 近些年, 随着自由基化学的迅速发展, 利用芳基重氮盐产生芳基自由基参与的环化反应也得到了迅速的发展. 整理了近十年来关于芳基重氮盐产生芳基自由基参与的环化反应的文献, 从芳基自由基对不饱和碳碳键、碳氮键的加成后构建各种环状化合物进行归纳. 最后, 对目前的研究进展进行了总结.

关键词： 芳基重氮盐; 芳基自由基; 不饱和键; 环化反应

本文引用格式

姜松 , 南宁 , 何景昊 , 郭嘉程 , 秦景灏 , 谢叶香 , 欧阳旋慧 , 宋仁杰 . 基于芳基重氮盐的芳基自由基介导的不饱和键环化反应研究进展[J]. 有机化学, 2022 , 42(12) : 3959 -3978 . DOI: 10.6023/cjoc202210013

Abstract

Aryldiazonium salts are widely used in organic synthesis due to their high reactivity and readily availability. As a common arylation reagent, aryl diazonium salts have been widely used in material chemistry, dye chemistry and medicinal chemistry by retaining and leaving N2 skeleton. In recent years, with the rapid development of radical chemistry, the cyclization reaction involving aryl radicals, which produced by aryldiazonium salts, has also been developed rapidly, and this strategy also stimulates the enthusiasm of organic chemists to construct various ring compounds. In this review, the addition of unsaturated carbon-carbon bonds and carbon-nitrogen bonds to construct various cyclic compounds from aryl radicals is summarized and classified according to the size of the cyclic compounds. Finally, the current research progress is summarized.

Key words： aryl diazonium salts; aryl radical; unsaturated bonds; cyclization

参考文献

[1]
(a) Xuan, S.-C.; Wang, X.-D.; Wang, J.-W.; Zhao, B.-L.; Cheng, K.; Qi, C.-Z. Chin. J. Org. Chem. 2014, 34, 1743. (in Chinese)
[1]
( 宣赏赐, 王晓丹, 王建伟, 赵保丽, 程凯, 齐陈泽, 有机化学, 2014, 34, 1743.)
[1]
(b) Zhao, X.-X.; Chang, H.-H.; Li, X.; Wei, W.-L. Chin. J. Org. Chem. 2015, 35, 478. (in Chinese)
[1]
( 赵晓霞, 常宏宏, 李兴, 魏文珑, 有机化学, 2015, 35, 478.)
[2]
Bai, Q.-F.; He, J.-Y.; Zhu, X.-Q.; Feng, G.-F.; Jin, C.-A. Chin. J. Org. Chem. 2019, 39, 527. (in Chinese)
[2]
( 白其凡, 何静耀, 祝小青, 冯高峰, 金城安, 有机化学, 2019, 39, 527.)
[3]
Liu, J.-D.; Jiang, J.-Y.; Zheng, L.-Y.; Liu, Z.-Q. Adv. Synth. Catal. 2020, 362, 4876.
[4]
Griefs, P. Justus Liebigs Ann. Chem. 1858, 106, 123.
[5]
Sandmeyer, T. Ber. Dtsch. Chem. Ges. 1884, 17, 2650.
[6]
Meerwein, H.; Büchner, E.; van Emster, K. J. Prakt. Chem. 1939, 152, 237.
[7]
Mo, F.-Y; Dong, G.-B; Zhang, Y.; Wang, J.-B. Org. Biomol. Chem. 2013, 11, 1582.
[8]
Babu, S.-S.; Muthuraja, P.; Yadav, P.; Gopinath, P. Adv. Synth. Catal. 2021, 363, 1782.
[9]
Medina-Mercado, I.; Porcel, S. Chem.-Eur. J. 2020, 26, 16206.
[10]
Oger, N.; Felpin, F.-X. ChemCatChem 2016, 8, 1998.
[11]
(a) Roglans, A.; Pla-Quintana, A.; Moreno-Manas, M. Chem. Rev. 2006, 106, 4622.
[11]
(b) He, L.; Qiu, G.; Gao, Y.; Wu, J. Org. Biomol. Chem. 2014, 12, 6965.
[11]
(c) Li, D.; Luo, Y.; Onidas, D.; He, L.; Jin, M.; Gazeau, F.; Pinson, J.; Mangeney, C. Adv. Colloid Interface Sci. 2021, 294, 102479.
[11]
(d) Mo, F.; Qiu, D.; Zhang, L.; Wang, J. Chem. Rev. 2021, 121, 5741.
[11]
(e) Zhang, F.-G.; Chen, Z.; Cheung, C. W.; Ma, J.-A. Chin. J. Chem. 2020, 38, 1132.
[11]
(f) Raicopol, M.; Pilan, L. Materials 2021, 14, 3857.
[12]
(a) Guo, W.; Lu, L. Q.; Wang, Y.; Wang, Y.-N.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., nt. Ed. 2015, 54, 2265.
[12]
(b) Yu, X.-L.; Chen, J.-R.; Chen, D.-Z.; Xiao, W.-J. Chem. Commun. 2016, 52, 8275.
[12]
(c) Ouyang, X.-H.; Li, Y.; Song, R.-J.; Hu, M.; Luo, S.; Li, J.-H. Sci. Adv. 2019, 5, eaav9839.
[12]
(d) Liu, J.; Xu, E.; Jiang, J.; Huang, Z.; Zheng, L.; Liu, Z.-Q. Chem. Commun. 2020, 56, 2202.
[12]
(e) Zhang, X.; Mei, Y.-Y.; Li, Y.-Y.; Hu, J.-G.; Huang, D.-Y.; Bi, Y.-C. Asian J. Org. Chem. 2021, 10, 453.
[12]
(f) Huang, J.; Ding, F.; Chen, Z.; Yang, G.; Wu, J. Org. Chem. Front. 2021, 8, 1461.
[12]
(g) Babu, S. S.; Muthuraja, P.; Yadav, P.; Gopinath, P. Adv. Synth. Catal. 2021, 363, 1782.
[13]
Chand, S.; Sharma, A. K.; Pandey, A. K.; Singh, K. N. Org. Lett. 2022, 24, 6423.
[14]
Sahoo, B.; Hopkinson, M. N.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 5505.
[15]
Jimoh, A.-A.; Hosseyni, S.; Ye, X.; Wojtas, L.; Hu, Y.; Shi, X. Chem. Commun. 2019, 55, 8150.
[16]
Fu, W.-J.; Xu, F.-J.; Fu, Y.-Q.; Zhu, M.; Yu, J.-Q.; Xu, C.; Zou, D.-P. J. Org. Chem. 2013, 78, 12202.
[17]
Tang, S.; Zhou, D.; Wang, Y.-C. Eur J. Org. Chem. 2014, 17, 3656.
[18]
Liu, T.; Zheng, D.-Q.; Wu, J. Org. Chem. Front. 2017, 4, 1079.
[19]
Guo, W.; Cheng, H.-G.; Chen, L.-Y.; Xuan, J.; Feng, Z.-J.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Adv. Synth. Catal. 2014, 356, 2787.
[20]
Felipe-Blanco, D.; Gonzalez-Gomez, J. C. Eur. J. Org. Chem. 2019, 2019, 7735.
[21]
Wang, Y.; Deng, L.-L.; Zhou, J.; Wang, X.-C.; Mei, H.-B; Han, J.-L; Pan, Y. Adv. Synth. Catal. 2018, 360, 1060.
[22]
Hartmann, M.; Studer, A. Angew. Chem., Int. Ed. 2014, 53, 8180.
[23]
An, Y.-Y.; Zheng, D.-Q.; Wu, J. Chem. Commun. 2014, 50, 11746.
[24]
Guo, R.; Yang, H.; Tang, P.-P. Chem. Commun. 2015, 51, 8829.
[25]
Micic, N.; Polyzos, A. Org. Lett. 2018, 20, 4663.
[26]
Shu, X.-Z.; Zhang, M.; He, Y.; Frei, H.; Toste, F.-D. J. Am. Chem. Soc. 2014, 136, 5844.
[27]
Kwon, S.-J.; Kim, D.-Y. Org. Lett. 2016, 18, 4562.
[28]
He, F.-S.; Wu, Y.-Q.; Li, X.-F.; Xia, H.-G.; Wu, J. Org. Chem. Front. 2019, 6, 1873.
[29]
Patil, D.-V.; Yun, H.; Shin, S. Adv. Synth. Catal. 2015, 357, 2622.
[30]
Alcaide, B.; Almendros, P.; Aparicio, B.; Lázaro-Milla, C.; Luna, A.; Faza, O.-N. Adv. Synth. Catal. 2017, 359, 2789.
[31]
Shen, Z.-J.; Wu, Y.-N.; He, C.-L.; He, L.; Hao, W.-J.; Wang, A.-F.; Tu, S.-J.; Jiang, B. Chem. Commun. 2018, 54, 445.
[32]
Wang, M.; Tang, B.-C.; Xiang, J.-C.; Chen, X.-L.; Ma, J.-T.; Wu, Y.-D.; Wu, A.-X. Org. Lett. 2019, 21, 8934.
[33]
Zhou, K.-D.; Chen, J.-Q.; Wu, J. Chin. Chem. Lett. 2020, 31, 2996.
[34]
Wang, X.-H; You, F.-Z.; Xiong, B.-J.; Chen, L.; Zhang, X.-M.; Lian, Z. RSC Adv. 2022, 12, 16745.
[35]
Liu, F.; Huang, J.-P.; Wu, X.-Y.; Du, F.-H.; Zeng, L.-H.; Wu, J.; Chen, Z.-Y. J. Org. Chem. 2022, 87, 6137.
[36]
Crespi, S.; J?ger, S.; K?nig, B.; Fagnoni, M. Eur. J. Org. Chem. 2017, 15, 2147.
[37]
Mkrtchyan, S.; Iaroshenko, V.-O. Chem. Commun. 2020, 56, 2606.
[38]
Wang, H.; Wang, B.; Sun, S.; Cheng, J. Org. Chem. Front. 2018, 5, 2547.
[39]
Yuan, L.; Jiang, S.-M.; Li, Z.-Z.; Zhu, Y.; Yu, J.; Li, L.; Li, M.-Z.; Tang, S.; Sheng, R.-R. Org. Biomol. Chem. 2018, 16, 2406.
[40]
Nair, A.-M.; Halder, I.; Khan, S.; Volla, C. M. R. Adv. Synth. Catal. 2020, 362, 224.
[41]
Xuan, J.; Gonzalez-Abradelo, D.; Strassert, C. A.; Daniliuc, C. G.; Studer, A. Eur. J. Org. Chem 2016, 29, 4961.
[42]
An, Y.-Y.; Zhang, J.; Xia, H.-G.; Wu, J. Org. Chem. Front. 2017, 4, 1318.
[43]
Li, J.; Zhang, W.-W.; Wei, X.-J.; Liu, F.; Hao, W.-J.; Wang, S.-L.; Li, G.; Tu, S.-J.; Jiang, B. J. Org. Chem. 2017, 82, 6621.
[44]
Liu, F.; Wang, J.-Y.; Zhou, P.; Li, G.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Angew. Chem., Int. Ed. 2017, 56, 15473.
[45]
Qin, B.-Y.; Huang, S.-X.; Chen, J.-Q.; Xiao, W.; Wu, J. Org. Chem. Front. 2022, 9, 3521.
[46]
Hari, D. P.; Hering, T.; K?nig, B. Org. Lett. 2012, 14, 5334.
[47]
Xia, Z.; Khaled, O.; Mouriès-Mansuy, V.; Ollivier, C.; Fensterbank, L. J. Org. Chem. 2016, 81, 7182.
[48]
Qu, C.-H.; Zhang, S.-L.; Du, H.-B.; Zhu, C.-J. Chem. Commun. 2016, 52, 14400.
[49]
Wang, Z.-S.; Tan, T.-D.; Wang, C.-M.; Yuan, D.-Q.; Zhang, T.; Zhu, P.-F.; Zhu, C.-Y.; Zhou, J.-M.; Ye, L.-W. Chem. Commun. 2017, 53, 6848.
[50]
Jin, C.; Su, L.-Z.; Ma, D.-X.; Cheng, M.-R. New J. Chem. 2017, 41, 14053.
[51]
Zhang, J.; Chen, J.; Zhai, Y.-H.; Yu, J.-T.; Pan, C.-D. Asian J. Org. Chem. 2022, 11, DOI: 10.1002/ajoc.202100671.
[52]
Liu, S.; Chen, K.; Hao, W.-J.; Tu, X.-C.; Tu, S.-J.; Jiang, B. J. Org. Chem. 2019, 84, 1964.
[53]
Shi, H.-N.; Huang, M.-H.; He, C.-L.; Lu, H.-P.; Hao, W.-J.; Tu, X.-C.; Tu, S.-J.; Jiang, B. J. Org. Chem. 2019, 84, 13686.
[54]
Huang, M.-H.; Shi, H.-N.; Zhu, C.-F.; He, C.-L.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Adv. Synth. Catal. 2019, 361, 5340.
[55]
Mayans, J. G.; Suppo, J. S.; Echavarren, A. M. Org. Lett. 2020, 22, 3045.
[56]
Zheng, D.-Q.; Yu, J.-Y.; Wu, J. Angew. Chem., Int. Ed. 2016, 55, 11925.
[57]
Alcaide, B.; Almendros, P.; Busto, E.; Herrera, F.; Lázaro-Milla, C.; Luna, A. Adv. Synth. Catal. 2017, 359, 2640.
[58]
An, Y.-Y.; Wu, J. Org. Lett. 2017, 19, 6028.
[59]
Medina-Mercado, I.; Colin-Molina, A.; Barquera-Lozada, J. E.; Rodríguez-Molina, B.; Porcel, S. ACS Catal. 2021, 11, 8968.
[60]
Bhat, V. S.; Lee, A. Adv. Synth. Catal. 2022, 364, 3088.
[61]
Yao, Y.-F.; Yin, Z.-Q.; He, F.-S.; Qin, X.-W.; Xie, W.-L.; Wu, J. Chem. Commun. 2021, 57, 2883.
[62]
Xiao, T.-B.; Dong, X.-C.; Tang, Y.-C.; Zhou, L. Adv. Synth. Catal. 2012, 354, 3195.
[63]
Wang, A.-F.; Hao, W.-J.; Zhu, Y.-L.; Li, G.-G.; Zhou, P.; Tu, S.-J.; Jiang, B. ACS Omega 2018, 3, 1482.
[64]
Liu, Y.; Wang, Q.-L.; Chen, Z.; Chen, P.; Tang, K.-W.; Zhou, Q.; Xie, J. Org. Biomol. Chem. 2019, 17, 10020.
[65]
Hegmann, N.; Prusko, L.; Heinrich, M. R. Org. Lett. 2017, 19, 2222.
[66]
Bansode, A. H.; Shaikh, S. R.; Gonnade, R. G.; Patil, N. T. Chem. Commun. 2017, 53, 9081.
[67]
Liu, Y.; Wang, Q.-L.; Chen, Z.; Zhou, Q.; Xiong, B.-Q.; Zhang, P.-L.; Tang, K.-W. Chem. Commun. 2019, 55, 12212.
[68]
Vidyasagar, A.; Shi, J.; Kreitmeier, P.; Reiser, O. Org. Lett. 2018, 20, 6984.
[69]
Xia, Z.-H.; Huang, J.-B.; He, Y.-M.; Zhao, J.-J.; Lei, J.; Zhu, Q. Org. Lett. 2014, 16, 2546.
[70]
Malviya, B. K.; Singh, K.; Jaiswal, P. K.; Karnatak, M.; Verma, V. P.; Badsara, S. S.; Sharma, S. New J. Chem. 2021, 45, 6367.
[71]
(a) Ghosh, I.; Marzo, L.; Das, A.; Shaikh, R.; Konig, B. Acc. Chem. Res. 2016, 49, 1566.
[71]
(b) Babu, S. S.; Muthuraja, P.; Yadav, P.; Gopinath, P. Adv. Synth. Catal. 2021, 363, 1782.
[72]
(a) Liu, Q.-Y.; Sun, B.-Q.; Liu, Z.; Kao, Y.; Dong, B.-W.; Jiang, S.-D.; Li, F.; Liu, G.-Y.; Yang, Y.; Mo, F.-Y. Chem. Sci. 2018, 9, 8731.
[72]
(b) Ouyang, X.-H.; Cheng, J.; Li, J.-H. Chem. Commun. 2018, 54, 8745.
[72]
(c) Jiang, Y.-Y.; Dou, G.-Y.; Zhang, L.-S.; Xu, K.; Little, R. D.; Zeng, C.-C. Adv. Synth. Catal. 2019, 361, 5170.
[72]
(d) Wang, P.; Yang, Z.-L.; Wang, Z.-W.; Xu, C.-Y.; Huang, L.; Wang, S.-C.; Zhang, H.; Lei, A.-W. Angew. Chem., Int. Ed. 2019, 58, 15747.
[73]
(a) Liang, Y.-Y.; Huang, J.; Ouyang, X.-H.; Qin, J.-H.; Song, R.-J.; Li, J.-H. Chem. Commun. 2021, 57, 3684.
[73]
(b) Huang, J.; Liang, Y.-Y.; Ouyang, X.-H.; Xiao, Y.-T.; Qin, J.-H.; Song, R.-J.; Li, J.-H. Org. Chem. Front. 2021, 8, 7009.
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