电化学条件下的Minisci反应研究进展

doi:10.6023/cjoc202102001

摘要/Abstract

Minisci反应是指亲核性的碳自由基与缺电子含氮芳杂环间发生的自由基取代反应, 是构建新的碳-碳键的一种重要方法. 另一方面, 作为一种绿色合成的技术和手段, 有机电合成近几年来再次受到人们的关注. 介绍了近期电化学条件下Minisci反应的研究进展.

关键词: Minisci反应, 有机电合成, 光电化学, 氧化还原反应

Minisci reaction, an important method for the construction of new carbon-carbon bonds, refers to one kind of the radical substitution reactions between a nucleophilic carbon radical and an electron-deficient nitrogen-containing aromatic heterocycle. Besides, organic electrosynthesis is experiencing a renaissance as a green synthesis technology and means. This review focuses on the recent advances in Minisci reactions under electrochemical conditions.

Key words: Minisci reactions, organic electrosynthesis, photoelectrochemistry, redox reactions

引用此文

孟薇, 徐坤, 郭兵兵, 曾程初. 电化学条件下的Minisci反应研究进展[J]. 有机化学, 2021, 41(7): 2621-2635.

Wei Meng, Kun Xu, Bingbing Guo, Chengchu Zeng. Recent Advances in Minisci Reactions under Electrochemical Conditions[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2621-2635.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 20

图1. Minisci反应的一般机理

Figure 1. General mechanism for the Minisci reactions

图2. 通过Minisci烷基化、羟甲基化或氨甲基化合成具有药用价值的化合物

Figure 2. Synthesis of compounds with medicinal value via Minisci alkylation, hydroxymethylation or aminomethylation

图3. Baran课题组的电化学条件下杂环芳烃的三氟甲基化反应

Figure 3. Trifluoromethylation of heterocyclic aromatic hydrocarbons under electrochemical conditions from Baran group

图4. 曾程初课题组的电化学条件下杂环芳烃的三氟甲基化反应

Figure 4. Trifluoromethylation of heterocyclic aromatic hydrocarbons under electrochemical conditions from Zeng group

图5. 王毅课题组的电化学条件下Minisci烷基化反应

Figure 5. Minisci alkylation reaction under electrochemical conditions from Wang group

图6. 曾程初课题组的镍催化电化学还原脱羧

Figure 6. Nickel-catalyzed electrochemical reductive decarboxylation from Zeng group

图7. 雷爱文课题组的电化学还原脱羧

Figure 7. Electrochemical reductive decarboxylation from Lei group

图8. 汪清民课题组的电化学还原脱羧

Figure 8. Electrochemical reductive decarboxylative from Wang group

图9. 微流控的氧化还原中性电化学平台上的NHPI酯的还原脱羧

Figure 9. Electrochemical reductive decarboxylative of NHPI ester in μRN-eChem

图10. 曾程初课题组的重氮盐电化学还原反应

Figure 10. Electrochemical reductive of aryldiazonium salts from Zeng group

图11. 雷爱文课题组的重氮盐的电化学还原反应

Figure 11. Electrochemical reductive of aryldiazonium salts from Lei group

图12. 徐海超课题组的有机三氟硼酸盐的Minisci光电烷基化反应

Figure 12. Photoelectrochemical Minisci alkylation of organotrifluoroborates from Xu group

图13. 徐海超课题组的羧酸的Minisci光电烷基化反应

Figure 13. Photoelectrochemical Minisci alkylation of carboxylic acids from Xu group

图14. 徐海超课题组的烷基草酸酯的Minisci光电烷基化反应

Figure 14. Photoelectrochemical Minisci alkylation of alkyl oxalates by Xu group

图15. Ackermann课题组的光电协调的三氟甲基化反应

Figure 15. Photoelectrochemical trifluoromethylation from Ackermann group

图16. Lambert课题组的杂芳烃与醚的电-光催化交叉偶联反应

Figure 16. Photoelectrochemical cross-coupling reaction of heteroarenes with ethers by Lambert group

图17. 徐海超课题组的杂环芳烃和脂肪烷烃的脱氢交叉偶联反应

Figure 17. Photoelectrochemical dehydrogenative cross-coupling of heteroarenes with aliphatic from Xu group

图18. 曾程初课题组的电催化Minisci酰基化反应

Figure 18. Electrocatalytic Minisci acylation reaction from Zeng group

图19. 曾程初课题组的镍催化Minisci电化学酰基化反应

Figure 19. Nickel-catalyzed electrochemical Minisci acylation from Zeng group

图20. 徐海超课题组的光电Minisci氨甲酰化反应

Figure 20. Photoelectrochemical Minisci carbamoylation reaction from Xu group

参考文献 19

[1]	(a) Duncton,M. A.J.; Estiarte,M. A.; Johnson,R. J.; Cox, M.; O'Mahony,D. J.R.; Edwards,W. T.; Kelly,M. G. J. Org. Chem. 2009, 74,6354. doi: 10.1021/jo9010624
	(b) Elwahy,A. H.M.; Abbas,A. A. J. Heterocycl. Chem. 2008, 45,1. doi: 10.1002/jhet.v45:1
	(c) Minisci, F.; Bernardi, R.; Bertini, F.; Galli, R.; Perchinummo, M. Tetrahedron 1971, 27,3575. doi: 10.1016/S0040-4020(01)97768-3
	(d) Liew,S. T.; Yang,L. -X. Curr. Pharm. Des. 2008, 14,1078. doi: 10.2174/138161208784246180
[2]	O'Brien,A. G.; Maruyama, A.; Inokuma, Y.; Fujita, M.; Baran,P. S.; Blackmond,D. G. Angew. Chem.,Int. Ed. 2014, 53,11868. doi: 10.1002/anie.201407948
[3]	Dou,G. -Y.; Jiang,Y. -Y.; Xu, K.; Zeng,C. -C. Org. Chem. Front. 2019, 6,2392. doi: 10.1039/C9QO00552H
[4]	Gao,Y. -Y.; Wu,Z. -G.; Yu, L.; Wang, Y.; Pan, Y. Angew. Chem.,Int. Ed. 2020, 59,10859. doi: 10.1002/anie.v59.27
[5]	Lian, F.; Xu, K.; Meng, W.; Zhang,H. -N.; Tan,Z. -M.; Zeng,C. -C. Chem. Commun. 2019, 55.14685. doi: 10.1039/C9CC07840A
[6]	Liu,Y. -C.; Xue,L. -W.; Shi,B. -Y.; Bu,F. -X.; Wang, D.; Lu,L. -J.; Shi,R. -Y.; Lei,A. -W. Chem. Commun. 2019, 55,14922. doi: 10.1039/C9CC08528A
[7]	Niu,K. -K.; Song,L. -Y.; Hao,Y. -K.; Liu,Y. -X.; Wang,Q. -M. Chem. Commun. 2020, 56,11673. doi: 10.1039/D0CC05391K
[8]	Mo,Y. -M.; Lu,Z. -H.; Rughoobur, G.; Patil, P.; Gershenfeld, N.; Akinwande,A. I.; Buchwald,S. L.; Jensen,K. F. Science 2020, 368,1352. doi: 10.1126/science.aba3823
[9]	Jiang,Y. -Y.; Dou,G. -Y.; Zhang,L. -S.; Xu, K.; Little,R. D.; Zeng,C. -C. Adv. Synth. Catal. 2019, 361,5170. doi: 10.1002/adsc.v361.22
[10]	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. doi: 10.1002/anie.v58.44
[11]	Yan, H.; Hou,Z. -W.; Xu,H. -C. Angew. Chem., Int. Ed. 2019, 58,4592. doi: 10.1002/anie.v58.14
[12]	Yatham,V. Y.; Bellotti, P.; König, B. Chem. Commun. 2019, 55,3489. doi: 10.1039/C9CC00492K
[13]	Lai,X. -L.; Shu,X. -M.; Song,J. -S.; Xu,H. -C. Angew. Chem.,Int. Ed. 2020, 59,10626. doi: 10.1002/anie.v59.26
[14]	Xu, F.; Lai,X. -L.; Xu,H. -C. Synlett 2020, 32,369. doi: 10.1055/a-1296-8652
[15]	Qiu,Y. -A.; Scheremetjew, A.; Finger,L. H.; Ackermann, L. Chem.- Eur. J. 2020, 26,3241. doi: 10.1002/chem.v26.15
[16]	Huang, H.; Strater,Z. M.; Lambert,T. H. J. Am. Chem. Soc. 2020, 142,1698. doi: 10.1021/jacs.9b11472
[17]	Xu, P.; Chen,P. -Y.; Xu,H. -C. Angew. Chem.,Int. Ed. 2020, 59,14275. doi: 10.1002/anie.v59.34
[18]	Wang,Q. -Q.; Xu, K.; Jiang,Y. -Y.; Liu,Y. -G.; Sun,B. -G.; Zeng,C. -C. Org. Lett. 2017, 19,5517. doi: 10.1021/acs.orglett.7b02589
[19]	Ding, H.; Xu, K.; Zeng,C. -C. J. Catal. 2020, 381,38. doi: 10.1016/j.jcat.2019.10.030