Synthesis of Nitrile via Electrochemical Appel Reaction

doi:10.6023/cjoc202202007

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (7): 2229-2235.DOI: 10.6023/cjoc202202007 Previous Articles Next Articles

ARTICLES

通过电化学Appel反应合成腈

李海琼, 尹梦云, 谢芬芬, 张正兵^*(), 韩盼^*(), 敬林海^*()

西华师范大学化学化工学院化学合成与污染控制四川省重点实验室四川南充 637002

收稿日期:2022-02-06 修回日期:2022-03-11 发布日期:2022-08-09
通讯作者: 张正兵, 韩盼, 敬林海
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(22001217); 四川省科技厅(2021ZYD0064); 西华师范大学英才基金(17YC020); 西华师范大学基本科研业务费(19D037); 西华师范大学基本科研业务费(19E034)

Synthesis of Nitrile via Electrochemical Appel Reaction

Haiqiong Li, Mengyun Yin, Fenfen Xie, Zhengbing Zhang(), Pan Han(), Linhai Jing()

Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong, Sichuan 637002

Received:2022-02-06 Revised:2022-03-11 Published:2022-08-09
Contact: Zhengbing Zhang, Pan Han, Linhai Jing
About author:
^† These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(22001217); Science and Technology Program of Sichuan Province(2021ZYD0064); Meritocracy Research Funds of China West Normal University(17YC020); Fundamental Research Funds of China West Normal University(19D037); Fundamental Research Funds of China West Normal University(19E034)

1. .pdf(4718KB)

Abstract

An electrochemical Appel reaction was developed for the synthesis of nitriles. This protocol features operationally simplicity, mild reaction conditions and environmental friendliness, enabling synthesis of various aromatic and aliphatic nitriles. Based on the controlled experiments and cyclic voltammetry (CV) experimental results, an electrochemical Appel reaction mechanism was proposed to explain the reaction process.

Key words: electrochemical synthesis, Appel reaction, dehydration of oximes, synthesis of nitriles

Cite this article

Haiqiong Li, Mengyun Yin, Fenfen Xie, Zhengbing Zhang, Pan Han, Linhai Jing. Synthesis of Nitrile via Electrochemical Appel Reaction[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2229-2235.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 8

References 26

[1]	(a) Dworczak, R.; Fabian, W. M. F.; Biza, P.; Weikmann, M.; Junek, H. Dyes Pigm. 1995, 28, 297. doi: 10.1016/0143-7208(95)00022-8
	(b) Dworczak, R.; Fabian, W. M. F.; Pawar, B. N.; Junek, H. Dyes Pigm. 1995, 29, 65. doi: 10.1016/0143-7208(95)00028-E
	(c) Pearce, E. M.; Weil, E. D.; Barinov, V. Y. Fire Smart Polymers (Fire and Polymers), American Chemical Society, 2001, pp. 37-48.
	(d) Amr, M. A.; Mohamed, H. E.; Mohamed, S. E.; Hesham, R. E.-S.; Ismail, A. A. Curr. Org. Synth. 2018, 15, 487. doi: 10.2174/1570179415666180403120140
[2]	Fatiadi, A. J. In Preparation and Synthetic Applications of Cyano Compounds, Eds.: Patai, S.; Rappaport, Z., Wiley, New York, 1983.
[3]	(a) Iyengar, B. S.; Dorr, R. T.; Remers, W. A. J. Med. Chem. 2004, 47, 218. doi: 10.1021/jm030225v pmid: 17228871
	(b) Romero, M.; Renard, P.; Caignard, D.-H.; Atassi, G.; Solans, X.; Constans, P.; Bailly, C.; Pujol, M. D. J. Med. Chem. 2007, 50, 294. pmid: 17228871
[4]	Pascual, E.; Sivera, F.; Yasothan, U.; Kirkpatrick, P. Nat. Rev. Drug Discov. 2009, 8, 191. doi: 10.1038/nrd2831 pmid: 19247302
[5]	Patat, A.; Paty, I.; Hindmarch, I. Hum. Psychopharmacol. 2001, 16, 369. doi: 10.1002/hup.310
[6]	(a) Sica, D. A.; Prisant, L. M. J. Clin. Hypertens. (Shelton, CT, U. S.) 2007, 9, 1. pmid: 19900016
	(b) Cooper-DeHoff, R. M.; Handberg, E. M.; Mancia, G.; Zhou, Q.; Champion, A.; Legler, U. F.; Pepine, C. J. Expert Rev. Cardiovasc. Ther. 2009, 7, 1329. doi: 10.1586/erc.09.102 pmid: 19900016
[7]	Noble, S.; McTavish, D. Drugs 1995, 50, 1032. pmid: 8612470
[8]	(a) Shu, Z.; Ye, Y.; Deng, Y.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2013, 52, 10573. doi: 10.1002/anie.201305731
	(b) Liu, J.; Zheng, H.-X.; Yao, C.-Z.; Sun, B.-F.; Kang, Y.-B. J. Am. Chem. Soc. 2016, 138, 3294. doi: 10.1021/jacs.6b00180
	(c) Ge, J.-J.; Yao, C.-Z.; Wang, M.-M.; Zheng, H.-X.; Kang, Y.-B.; Li, Y. Org. Lett. 2016, 18, 228. doi: 10.1021/acs.orglett.5b03367
	(d) Yu, L.; Li, H.; Zhang, X.; Ye, J.; Liu, J.; Xu, Q.; Lautens, M. Org. Lett. 2014, 16, 1346. doi: 10.1021/ol500075h
	(e) Zhuang, Y.-J.; Liu, J.; Kang, Y.-B. Tetrahedron Lett. 2016, 57, 5700. doi: 10.1016/j.tetlet.2016.11.034
[9]	(a) Zhou, S.; Addis, D.; Das, S.; Junge, K.; Beller, M. Chem. Commun. 2009, 4883. pmid: 29320204
	(b) Shipilovskikh, S. A.; Vaganov, V. Y.; Denisova, E. I.; Rubtsov, A. E.; Malkov, A. V. Org. Lett. 2018, 20, 728. doi: 10.1021/acs.orglett.7b03862 pmid: 29320204
[10]	(a) Zhou, W.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 7094. doi: 10.1002/anie.200903838
	(b) Tseng, K.-N. T.; Rizzi, A. M.; Szymczak, N. K. J. Am. Chem. Soc. 2013, 135, 16352. doi: 10.1021/ja409223a
	(c) Guo, S.; Wan, G.; Sun, S.; Jiang, Y.; Yu, J.-T.; Cheng, J. Chem. Commun. 2015, 51, 5085. doi: 10.1039/C5CC01024A
[11]	(a) Anderson, B. A.; Bell, E. C.; Ginah, F. O.; Harn, N. K.; Pagh, L. M.; Wepsiec, J. P. J. Org. Chem. 1998, 63, 8224. doi: 10.1021/jo9808674
	(b) Zanon, J.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 2890. doi: 10.1021/ja0299708
	(c) Cristau, H.-J.; Ouali, A.; Spindler, J.-F.; Taillefer, M. Chem.-Eur. J. 2005, 11, 2483. doi: 10.1002/chem.200400979
	(d) Pan, S.; Wu, F.; Yu, R.; Chen, W. J. Org. Chem. 2016, 81, 1558. doi: 10.1021/acs.joc.5b02710
	(e) Yan, G.; Zhang, Y.; Wang, J. Adv. Synth. Catal. 2017, 359, 4068. doi: 10.1002/adsc.201700875
[12]	(a) Fang, C.; Li, M.; Hu, X.; Mo, W.; Hu, B.; Sun, N.; Jin, L.; Shen, Z. RSC Adv. 2017, 7, 1484. doi: 10.1039/C6RA26435B pmid: 33795972
	(b) Murugesan, K.; Senthamarai, T.; Sohail, M.; Sharif, M.; Kalevaru, N. V.; Jagadeesh, R. V. Green Chem. 2018, 20, 266. doi: 10.1039/C7GC02627G pmid: 33795972
	(c) Chen, H.; Sun, S.; Xi, H.; Hu, K.; Zhang, N.; Qu, J.; Zhou, Y. Tetrahedron Lett. 2019, 60, 1434. doi: 10.1016/j.tetlet.2019.04.043 pmid: 33795972
	(d) Zhan, W.; Tong, M.; Ji, L.; Zhang, H.; Ge, Z.; Wang, X.; Li, R.. Chin. Chem. Lett. 2019, 30, 973. doi: 10.1016/j.cclet.2019.01.006 pmid: 33795972
	(e) Mudshinge, S. R.; Potnis, C. S.; Xu, B.; Hammond, G. B. Green Chem. 2020, 22, 4161. doi: 10.1039/d0gc00757a pmid: 33795972
	(f) Hua, M.; Song, J.; Huang, X.; Liu, H.; Fan, H.; Wang, W.; He, Z.; Liu, Z.; Han, B. Angew. Chem., Int. Ed. 2021, 60, 21479. doi: 10.1002/anie.202107996 pmid: 33795972
[13]	(a) Xu, J.-H.; Jiang, Q.; Guo, C.-C. J. Org. Chem. 2013, 78, 11881. doi: 10.1021/jo401919h
	(b) Preger, Y.; Root, T. W.; Stahl, S. S. ACS Omega 2018, 3, 6091. doi: 10.1021/acsomega.8b00911
	(c) Vanoye, L.; Hammoud, A.; Gérard, H.; Barnes, A.; Philippe, R.; Fongarland, P.; de Bellefon, C.; Favre-Réguillon, A. ACS Catal. 2019, 9, 9705. doi: 10.1021/acscatal.9b02779
	(d) Murata, Y.; Iwasa, H.; Matsumura, M.; Yasuike, S. Chem. Pharm. Bull. 2020, 68, 679. doi: 10.1248/cpb.c20-00228
	(e) Takahashi, Y.; Tsuji, H.; Kawatsura, M. J. Org. Chem. 2020, 85, 2654. doi: 10.1021/acs.joc.9b02705
	(f) Lu, D.; Cui, J.; Yang, S.; Gong, Y. ACS Catal. 2021, 11, 4288. doi: 10.1021/acscatal.1c00557
	(g) Xiao, J.; Guo, F.; Li, Y.; Li, F.; Li, Q.; Tang, Z.-L. J. Org. Chem. 2021, 86, 2028. doi: 10.1021/acs.joc.0c02794
[14]	(a) Li, Y.-T.; Liao, B.-S.; Chen, H.-P.; Liu, S.-T. Synthesis 2011, 2639. pmid: 30240220
	(b) Ma, X.-Y.; He, Y.; Lu, T.-T.; Lu, M. Tetrahedron 2013, 69, 2560. doi: 10.1016/j.tet.2013.01.059 pmid: 30240220
	(c) Ghosh, P.; Pariyar, G. C.; Saha, B.; Subba, R. Synth. Commun. 2016, 46, 685. doi: 10.1080/00397911.2016.1167910 pmid: 30240220
	(d) Hyodo, K.; Kitagawa, S.; Yamazaki, M.; Uchida, K. Chem. Asian J. 2016, 11, 1348. doi: 10.1002/asia.201600085 pmid: 30240220
	(e) Rapeyko, A.; Climent, M. J.; Corma, A.; Concepción, P.; Iborra, S. ACS Catal. 2016, 6, 4564. doi: 10.1021/acscatal.6b00272 pmid: 30240220
	(f) Sun, D.; Kitamura, E.; Yamada, Y.; Sato, S. Green Chem. 2016, 18, 3389. doi: 10.1039/C6GC00384B pmid: 30240220
	(g) Ding, R.; Liu, Y.; Han, M.; Jiao, W.; Li, J.; Tian, H.; Sun, B. J. Org. Chem. 2018, 83, 12939. doi: 10.1021/acs.joc.8b02190 pmid: 30240220
	(h) Zhang, D.; Huang, Y.; Zhang, E.; Yi, R.; Chen, C.; Yu, L.; Xu, Q. Adv. Synth. Catal. 2018, 360, 784. doi: 10.1002/adsc.201701154 pmid: 30240220
	(i) Ma, X.; Liu, D.; Chen, Z. Synth. Commun. 2021, 51, 3261. doi: 10.1080/00397911.2021.1943752 pmid: 30240220
[15]	(a) Sperry, J. B.; Wright, D. L. Chem. Soc. Rev. 2006, 35, 605. doi: 10.1039/b512308a pmid: 29498518
	(b) Jutand, A. Chem. Rev. 2008, 108, 2300. doi: 10.1021/cr068072h pmid: 29498518
	(c) Yoshida, J.-I.; Kataoka, K.; Horcajada, R.; Nagaki, A. Chem. Rev. 2008, 108, 2265. doi: 10.1021/cr0680843 pmid: 29498518
	(d) Francke, R.; Little, R. D. Chem. Soc. Rev. 2014, 43, 2492. doi: 10.1039/c3cs60464k pmid: 29498518
	(e) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230. doi: 10.1021/acs.chemrev.7b00397 pmid: 29498518
	(f) Ma, C.; Fang, P.; Mei, T.-S. ACS Catal. 2018, 8, 7179. doi: 10.1021/acscatal.8b01697 pmid: 29498518
	(g) Moeller, K. D. Chem. Rev. 2018, 118, 4817. doi: 10.1021/acs.chemrev.7b00656 pmid: 29498518
	(h) Yoshida, J.-I.; Shimizu, A.; Hayashi, R. Chem. Rev. 2018, 118, 4702. doi: 10.1021/acs.chemrev.7b00475 pmid: 29498518
	(i) Marken, F.; Wadhawan, J. D. Acc. Chem. Res. 2019, 52, 3325. doi: 10.1021/acs.accounts.9b00480 pmid: 29498518
	(j) Xiong, P.; Xu, H.-C. Acc. Chem. Res. 2019, 52, 3339. doi: 10.1021/acs.accounts.9b00472 pmid: 29498518
	(k) Yuan, Y.; Lei, A. Acc. Chem. Res. 2019, 52, 3309. doi: 10.1021/acs.accounts.9b00512 pmid: 29498518
	(l) Jiao, K.-J.; Xing, Y.-K.; Yang, Q.-L.; Qiu, H.; Mei, T.-S. Acc. Chem. Res. 2020, 53, 300. doi: 10.1021/acs.accounts.9b00603 pmid: 29498518
	(m) Siu, J. C.; Fu, N.; Lin, S. Acc. Chem. Res. 2020, 53, 547. doi: 10.1021/acs.accounts.9b00529 pmid: 29498518
[16]	(a) Mo, Z.-Y.; Swaroop, T. R.; Tong, W.; Zhang, Y.-Z.; Tang, H.-T.; Pan, Y.-M.; Sun, H.-B.; Chen, Z.-F. Green Chem. 2018, 20, 4428. doi: 10.1039/C8GC02143K
	(b) Zhang, Y.-Z.; Mo, Z.-Y.; Wang, H.-S.; Wen, X.-A.; Tang, H.-T.; Pan, Y.-M. Green Chem. 2019, 21, 3807. doi: 10.1039/C9GC01201J
	(c) Wang, X.-Y.; Zhong, Y.-F.; Mo, Z.-Y.; Wu, S.-H.; Xu, Y.-L.; Tang, H.-T.; Pan, Y.-M. Adv. Synth. Catal. 2021, 363, 208. doi: 10.1002/adsc.202001192
	(d) Wu, Y.; Chen, J.-Y.; Liao, H.-R.; Shu, X.-R.; Duan, L.-L.; Yang, X.-F.; He, W.-M. Green Synth. Catal. 2021, 2, 233.
	(e) Yang, Z.; Yu, Y.; Lai, L.; Zhou, L.; Ye, K.; Chen, F.-E. Green Synth. Catal. 2021, 2, 19.
	(f) Zhang, S.; Ye, X.; Wojtas, L.; Hao, W.; Shi, X. Green Synth. Catal. 2021, 2, 82.
[17]	Libendi, S. S.; Demizu, Y.; Onomura, O. Org. Biomol. Chem. 2009, 7, 351. doi: 10.1039/B816598J
[18]	(a) Cui, T.; Zhan, Y.; Dai, C.; Lin, J.; Liu, P.; Sun, P. J. Org. Chem. 2021, 86, 15897. doi: 10.1021/acs.joc.0c03026
	(b) Gao, J.; Weng, X.; Ma, C.; Xu, X.; Fang, P.; Mei, T. Chin. J. Org. Chem. 2021, 41, 3223. (in Chinese) doi: 10.6023/cjoc202103049
	( 高君青, 翁信军, 马聪, 徐学涛, 方萍, 梅天胜, 有机化学, 2021, 41, 3223.) doi: 10.6023/cjoc202103049
[19]	Dai, J.-J.; Huang, Y.-B.; Fang, C.; Guo, Q.-X.; Fu, Y. ChemSusChem 2012, 5, 617. doi: 10.1002/cssc.201100776
[20]	Ye, J.-Q.; Zhang, Z.-L.; Zha, Z.-G.; Wang, Z.-Y. Chin. Chem. Lett. 2014, 25, 1112. doi: 10.1016/j.cclet.2014.04.024
[21]	Qu, Q.; Gao, X.; Gao, J.; Yuan, G. Sci. China Chem. 2015, 58, 747. doi: 10.1007/s11426-015-5331-z
[22]	Shono, T.; Matsumura, Y.; Tsubata, K.; Kamada, T.; Kishi, K.. J. Org. Chem. 1989, 54, 2249. doi: 10.1021/jo00270a044
[23]	Hartmer, M. F.; Waldvogel, S. R. Chem. Commun. 2015, 51, 16346. doi: 10.1039/C5CC06437F
[24]	(a) Ohmori, H.; Nakai, S.; Sekiguchi, M.; Masui, M. Chem. Pharm. Bull. 1980, 28, 910. doi: 10.1248/cpb.28.910
	(b) Xu, Z.; Zheng, Y.; Wang, Z.; Shao, X.; Tian, L.; Wang, Y. Chem. Commun. 2019, 55, 15089. doi: 10.1039/C9CC08622F
[25]	(a) de Andrade, V. S. C.; de Mattos, M. C. S. Curr. Org. Synth. 2015, 12, 309. doi: 10.2174/1570179412666150305231358
	(b) Li, Z.; Sun, W.; Wang, X.; Li, L.; Zhang, Y.; Li, C. J. Am. Chem. Soc. 2021, 143, 3536. doi: 10.1021/jacs.0c13093
[26]	(a) Ban, Y.-L.; Dai, J.-L.; Jin, X.-L.; Zhang, Q.-B.; Liu, Q. Chem. Commun. 2019, 55, 9701. doi: 10.1039/C9CC05354A
	(b) Schäfer, R. J. B.; Monaco, M. R.; Li, M.; Tirla, A.; Rivera- Fuentes, P.; Wennemers, H. J. Am. Chem. Soc. 2019, 141, 18644. doi: 10.1021/jacs.9b07632

Entry	Electrolyte	Solvent	Base	Yield^b/%
1	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	67
2^c	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	33
3^d	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	26
4^e	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	48
5	ⁿBu₄NBF₄	CH₃CN	NaHCO₃	41
6	Me₄NBF₄	CH₃CN	NaHCO₃	55
7	ⁿBu₄NClO₄	CH₃CN	NaHCO₃	60
8	LiClO₄	CH₃CN	NaHCO₃	11
9	TBAB	CH₃CN	NaHCO₃	85 (83)^f
10	TBAI	CH₃CN	NaHCO₃	60
11	TBAB	CH₃CN	Na₂CO₃	70
12	TBAB	CH₃CN	K₃PO₄	46
13	TBAB	CH₃CN	Cs₂CO₃	69
14	TBAB	CH₃CN	Et₃N	44
15	TBAB	THF	NaHCO₃	0
16	TBAB	DCM	NaHCO₃	48
17	TBAB	DMF	NaHCO₃	15
18	TBAB	Dioxane	NaHCO₃	0
19^g	TBAB	CH₃CN	NaHCO₃	64
20^h	TBAB	CH₃CN	NaHCO₃	57
21ⁱ	TBAB	CH₃CN	NaHCO₃	50
22^j	TBAB	CH₃CN	NaHCO₃	0

Entry	Electrolyte	Solvent	Base	Yield^b/%
1	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	67
2^c	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	33
3^d	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	26
4^e	ⁿBu₄NPF₆	CH₃CN	NaHCO₃	48
5	ⁿBu₄NBF₄	CH₃CN	NaHCO₃	41
6	Me₄NBF₄	CH₃CN	NaHCO₃	55
7	ⁿBu₄NClO₄	CH₃CN	NaHCO₃	60
8	LiClO₄	CH₃CN	NaHCO₃	11
9	TBAB	CH₃CN	NaHCO₃	85 (83)^f
10	TBAI	CH₃CN	NaHCO₃	60
11	TBAB	CH₃CN	Na₂CO₃	70
12	TBAB	CH₃CN	K₃PO₄	46
13	TBAB	CH₃CN	Cs₂CO₃	69
14	TBAB	CH₃CN	Et₃N	44
15	TBAB	THF	NaHCO₃	0
16	TBAB	DCM	NaHCO₃	48
17	TBAB	DMF	NaHCO₃	15
18	TBAB	Dioxane	NaHCO₃	0
19^g	TBAB	CH₃CN	NaHCO₃	64
20^h	TBAB	CH₃CN	NaHCO₃	57
21ⁱ	TBAB	CH₃CN	NaHCO₃	50
22^j	TBAB	CH₃CN	NaHCO₃	0

通过电化学Appel反应合成腈

Synthesis of Nitrile via Electrochemical Appel Reaction

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 8

References 26

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[2]	Junying Zhang, Xiaojing Zhao, Ganpeng Li, Yonghui He. Electrochemical Synthesis of Masked Organoboronic Acids RB(dan) at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1815-1823.
[3]	Yongzhou Pan, Xiujin Meng, Yingchun Wang, Muxue He. Recent Progress in Electrochemical Fixation of CO₂ to Construct Carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1416-1434.
[4]	Jiawei Huang, Xiaoman Li, Liang Xu, Yu Wei. Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 756-762.
[5]	Zhengjiang Fu, Zhenjiang Yang, Li Sun, Jian Yin, Xuezheng Yi, Hu Cai, Aiwen Lei. Electrochemical Synthesis of Aryl Sulfonates from Sodium Sulfinates and Phenols under Metal-Free Conditions [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 600-606.
[6]	Xiaolong Guo, Yuxian Wang, Zhiqiang Zhao, Qing Wang, Jian Zuo, Luyao Wang. Electrochemical Oxidative C—H Trifluoromethylation of Quinoxalin-2(1H)-ones and the Performance Evaluation via Electro-descriptors [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 641-649.
[7]	Hongxia Li, Peng Chen, Zhilin Wu, Yuhan Lu, Junmei Peng, Jingyang Chen, Weimin He. Electrochemical Oxidative Cross-Dehydrogenative Coupling of Five-Membered Aromatic Heterocycles with NH₄SCN [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3398-3404.
[8]	Zhiheng Zhao, Ming Li, Yaqin Zhou, Yonghui He, Lizhu Zhang, Ganpeng Li, Lijun Gu. Synthesis of 1,2,4-Triazoles via the Electrochemical Oxidative [3+2] Annulation [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2476-2484.
[9]	Yaqin Zhou, Zhiheng Zhao, Liang Zeng, Ming Li, Yonghui He, Lijun Gu. Recent Advance in Organic Electrochemical Synthesis of Nitrogenous Heterocyclic Compounds Involving Haloids as Mediators [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1072-1080.
[10]	Dandan Li, Xiaochen Wang, Shanshan Li, Chenyu Fu, Qianqian Li, Dongtao Xu, Yingying Ma. Recent Advances in Electrochemical C(3)—H Functionalization of Quinoxalin-2(1H)-ones [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4610-4622.
[11]	Wenyi Li, Yinheng Tang, Wentao Ouyang, Yuhan Lu, Jinyang Chen, Weimin He. Electrochemical Selenylation of N-Unprotected Anilines for Consturcing 4-(Organylselanyl)anilines [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4766-4772.
[12]	Hongyu Wu, Xianyong Yu, Zhong Cao. Electrochemical Multicomponent Synthesis of α-Ketoamides from α-Oxocarboxylic Acids, Isocyanides and Water [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4712-4717.
[13]	Wei Cai, You Huang. Advances in Organophosphorus Redox Catalysis [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3903-3913.
[14]	Zhang Huaiyuan, Tang Rongping, Shi Xingli, Xie Lin, Wu Jiawei. Recent Advances in Organic Electrochemical Synthesis and Application of Hypervalent Iodine Reagents [J]. Chin. J. Org. Chem., 2019, 39(7): 1837-1845.
[15]	Wu Yaxing, Xi Yachao, Zhao Ming, Wang Siyi. Progress in Electrochemical C—H Functionalizations of Aromatic Compounds [J]. Chin. J. Org. Chem., 2018, 38(10): 2590-2605.