Recent Advances in Minisci Reactions under Electrochemical Conditions

doi:10.6023/cjoc202102001

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2621-2635.DOI: 10.6023/cjoc202102001 Previous Articles Next Articles

Special Issue: 有机电合成虚拟专辑；热点论文虚拟合集

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电化学条件下的Minisci反应研究进展

孟薇, 徐坤, 郭兵兵, 曾程初^*()

北京工业大学环境与生命学部北京 100124

收稿日期:2021-02-01 修回日期:2021-02-22 发布日期:2021-03-22
通讯作者: 曾程初
基金资助:
国家自然科学基金(21871019)

Recent Advances in Minisci Reactions under Electrochemical Conditions

Wei Meng, Kun Xu, Bingbing Guo, Chengchu Zeng()

Faculty of Environment and Life Sciences, Beijing University of Technology, Beijing 100124

Received:2021-02-01 Revised:2021-02-22 Published:2021-03-22
Contact: Chengchu Zeng
Supported by:
National Natural Science Foundation of China(21871019)

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

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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.

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Fig. & Tab. 20

Figure 1. General mechanism for the Minisci reactions

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

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

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

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

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

Figure 7. Electrochemical reductive decarboxylation from Lei group

Figure 8. Electrochemical reductive decarboxylative from Wang group

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

Figure 10. Electrochemical reductive of aryldiazonium salts from Zeng group

Figure 11. Electrochemical reductive of aryldiazonium salts from Lei group

Figure 12. Photoelectrochemical Minisci alkylation of organotrifluoroborates from Xu group

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

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

Figure 15. Photoelectrochemical trifluoromethylation from Ackermann group

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

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

Figure 18. Electrocatalytic Minisci acylation reaction from Zeng group

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

Figure 20. Photoelectrochemical Minisci carbamoylation reaction from Xu group

References 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

电化学条件下的Minisci反应研究进展

Recent Advances in Minisci Reactions under Electrochemical Conditions

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