Recent Progress on the Electrochemical Difunctionalization of Alkenes/Alkynes

doi:10.6023/cjoc202204066

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (12): 4169-4201.DOI: 10.6023/cjoc202204066 Previous Articles Next Articles

Special Issue: 自由基化学专辑

REVIEWS

电化学促进的烯烃和炔烃双官能团化反应研究进展

李秀英, 陶萍芳, 程泳渝, 胡琼, 黄伟娟, 李芸, 罗志辉^*(), 黄国保^*()

玉林师范学院广西农产资源化学与生物技术重点实验室广西玉林 537000

收稿日期:2022-04-27 修回日期:2022-06-13 发布日期:2022-09-08
通讯作者: 罗志辉, 黄国保
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(21961042); 广西高校中青年教师基础能力提升(2021KY0587); 广西高校中青年教师基础能力提升(2022KY0572); 玉林师范学院科研(G2021ZK16); 玉林师范学院科研(G2022ZK08)

Recent Progress on the Electrochemical Difunctionalization of Alkenes/Alkynes

Xiuying Li, Pingfang Tao, Yongyu Cheng, Qiong Hu, Weijuan Huang, Yun Li, Zhihui Luo(), Guobao Huang()

Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology, Yulin Normal University, Yulin, Guangxi 537000

Received:2022-04-27 Revised:2022-06-13 Published:2022-09-08
Contact: Zhihui Luo, Guobao Huang
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21961042); Basic Ability Improvement Project of Young and Middle-Aged Teachers in Guangxi Colleges(2021KY0587); Basic Ability Improvement Project of Young and Middle-Aged Teachers in Guangxi Colleges(2022KY0572); Program of Yulin Normal University(G2021ZK16); Program of Yulin Normal University(G2022ZK08)

The difunctionalization of unsaturated hydrocarbons (alkenes or alkynes) is an important strategy to introduce functional groups, and is also an important method to synthesize polysubstituted hydrocarbons, which is widely used in the fields of total synthesis of natural products and drug synthesis. The latest research progress on the electrochemically enabled difunctionalization of alkenes or alkynes in recent five years is summarized. According to the classification of difunctionalization of alkenes and cyclization of unsaturated hydrocarbon, the application and the related reaction mechanism are introduced. It is hoped that this review can be referred to the future application in organic synthesis of electrochemic- mediated difunctionalization of alkenes/alkynes.

Key words: electrochemistry, alkenes/alkynes, difunctionalization

Cite this article

Xiuying Li, Pingfang Tao, Yongyu Cheng, Qiong Hu, Weijuan Huang, Yun Li, Zhihui Luo, Guobao Huang. Recent Progress on the Electrochemical Difunctionalization of Alkenes/Alkynes[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4169-4201.

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Fig. & Tab. 71

Scheme 1. Electrochemically mediated trifluoromethylation of alkene amination

Scheme 2. Electrochemically mediated intermolecular oxidative trifluoromethylation and amino trifluoromethylation of olefins

Scheme 3. Electrochemically mediated azide oxidation of alkenes

Scheme 4. Electrochemical difluoromethylation of electron-deficient alkenes

Scheme 5. Electrochemical oxidative alkoxysulfonylation of alkenes

Scheme 6. Electrochemical oxidation-induced difunctionalization of alkynes and alkenes with sulfonyl hydrazides

Scheme 7. Electrochemical sulfonylation/heteroarylation of alkenes

Scheme 8. Electrochemically mediated olefin sulfonylation

Scheme 9. Electrochemically mediated alkoxy sulfonation of alkenes

Scheme 10. Electrochemically mediated amination sulfonation of alkenes

Scheme 11. Electrochemically mediated sulfonation of alkenes

Scheme 12. Electrochemically mediated olefin formylation reaction

Scheme 13. Electrochemically mediated oxyketonation of olefins

Scheme 14. Electrochemically enabled carbohydroxylation of alkenes

Scheme 15. Electrochemical dimethoxylation of olefins

Scheme 16. Electrochemical synthesis of aryl ethylene imides

Scheme 17. Electrochemical diazotization of alkenes

Scheme 18. Electrocatalytic radical dichlorination of alkenes

Scheme 19. Electrochemically catalyzed chloroalkylation of alkenes

Scheme 20. Electrochemically mediated acyloxylation/trifluoromethylation of styrene derivatives

Scheme 21. Cu-electrocatalytic diazidation of alkenes

Scheme 22. Cathodic regioselective coupling of aliphatic ketones with alkenes

Scheme 23. Cathodic regioselective coupling of aliphatic ketones with alkenes

Scheme 24. Electrochemical multi-component reaction of potassium metabisulfite with alkenes and alcohols enabling synthesis of sulfonate esters

Scheme 25. Difunctionalization of unactivated olefins via selective electrochemical chlorosulfuration or chlorosulfoxidation

Scheme 26. Scalable electrocatalytic intermolecular acylcyanation and aminocyanation of alkenes

Scheme 27. Electrochemical organoselenium-catalyzed Intermolecular hydroazolylation of alkenes

Scheme 28. Electrochemically mediated indolylation of styrene derivatives

Scheme 29. Electrochemically mediated iodoazide of styrene derivatives

Scheme 30. Electrochemical difluorination of alkenes

Scheme 31. Electrocatalytic synthesis of gem-bisarylthio enamines and α-phenylthio ketones

Scheme 32. Electrochemically enabled chemoselective sulfonylation and hydrazination of indoles

Scheme 33. Electroreductive carbofunctionalization of alkenes with alkyl bromides

Scheme 34. Electrochemical construction of nitrogen heterocycles

Scheme 35. Electrochemically mediated synthesis of γ- and δ- lactam from N-phenylamide

Scheme 36. Electrocatalytic intramolecular dehydrogenation cyclization of N-aryl enylamine

Scheme 37. Synthesis of selenoindolones by cyclization of acrylamide

Scheme 38. Electrochemically mediated bifunctional selenization of terminal alkenes

Scheme 39. Electrochemical mediated intramolecular selenidation/cyclization of alkenes

Scheme 40. Synthesis of chlorotrifluoromethylated pyrrolidines by electrocatalytic radical ene-yne cyclization

Scheme 41. Electrochemically mediated tandem sulfonylation cyclization of ortho-aminoalkene radicals

Scheme 42. Electrochemically mediated trifluoromethyl cyclization of N-arylacrylamides

Scheme 43. Electrochemically mediated trifluoromethylation/ C(sp2)—H functionalization of arylacrylamides

Scheme 44. Electrochemically mediated enol trifluoromethylation to synthesize morpholine derivatives

Scheme 45. Electrochemically mediated enol trifluoromethylation cyclization to synthesize seven-membered heterocycles

Scheme 46. Electrochemically mediated cyclization of N-cyanamide alkene trifluoromethylation

Scheme 47. Electrochemically mediated difluoromethylation cyclization of diphenylalkenes

Scheme 48. Electrochemical sulfonylation-induced lactonization of alkenes: synthesis of sulfonyl phthalides

Scheme 49. Electrocatalytic oxidative hydrofunctionalization reactions of alkenes via Co-cycle

Scheme 50. Electrochemically enabled synthesis of imidazo-fused N—Heteroaromatic compounds through (3+2) annulation reaction of heteroarylamines with intramolecular alkynes

Scheme 51. Electrochemically mediated C—H/N—H functionalization synthesis of (aza)indole

Scheme 52. Modification of ethinylestradiol derivatives under electrochemical conditions

Scheme 53. Electrochemical synthesis of benzoxazolone derivatives

Scheme 54. Electrochemical synthesis of benzoxazolones and their subsequent transformations

Scheme 55. Electrooxidative tandem cyclization of activated alkynes with sulfinic acids to sulfonated indenones

Scheme 56. Electrochemically enabled synthesis of 2,1-ben- zoxazoles from o?nitrophenylacetylenes

Scheme 57. Electrochemically mediated radical tandem cyclization of alkynes

Scheme 58. Electrosynthesis of azaheterocycles through anodic oxidation cyclization of 1,6-enynes

Scheme 59. Electrochemically mediated synthesis of aziridine from triaryl-substituted alkenes and sulfamate

Scheme 60. Electrochemical dehydrogenation cyclization of alkenes with 1,2- or 1,3-diol

Scheme 61. Electrochemical synthesis of isoquinolone derivatives from ethylene/acetylene and aryl/vinyl amides

Scheme 62. Electrochemically mediated cyclization of alkenes with tertiary aniline [4+2] to form tetrahydroquinoline

Scheme 63. Electrochemical synthesis of quinazolinones from alkenes and 2-aminobenzamides

Scheme 64. Three-component reaction of electrochemical oxidation of o-aminostyrene, carbon dioxide and secondary amine

Scheme 65. Electrochemically mediated cyclization of N-2-pyridyl hydrazine with inner alkynes

Scheme 66. Ruthenium/electrochemical dehydroalkyne cyclization

Scheme 67. Electrochemical mediated decarboxylation [4+2] of aryl glyoxylic acid with inner alkynes

Scheme 68. Synthesis of 1?naphthols by intermolecular annulation of alkynes with 1,3-dicarbonyl compounds

Scheme 69. Electrochemically mediated dehydrogenation coupling of amides and alkenes

Scheme 70. Electrochemical oxidative [4+2] annulation for the unfunctionalized heterobiaryl compounds

Scheme 71. One-pot two-step electrosynthesis of cinnoline derivatives

References 89

[1]	(a) Lan, X. W.; Wang, N. X.; Xing, Y. Eur. J. Org. Chem. 2017, 2017, 5821. doi: 10.1002/ejoc.201700678
	(b) Chen, X.; Xiao, F.; He, W. M. Org. Chem. Front. 2021, 8, 5206. doi: 10.1039/D1QO00375E
[2]	Mei, H.; Yin, Z.; Liu, J.; Sun, H.; Han, J. Chin. J. Chem. 2019, 37, 292.
[3]	(a) Steckhan, E.; Arns, T.; Heineman, W. R.; Hilt, G.; Hoormann, D.; Jorissen, J.; Kroner, L.; Lewall, B.; Putter, H. Chemosphere 2001, 43, 63. pmid: 24500279
	(b) Frontana-Uribe, B. A.; Little, R. D.; Ibanez, J. G.; Palma, A.; Vasquez-Medrano, R. Green Chem. 2010, 12, 2099. doi: 10.1039/c0gc00382d pmid: 24500279
	(c) Francke, R.; Little, R. D. Chem. Soc. Rev. 2014, 43, 2492. doi: 10.1039/c3cs60464k pmid: 24500279
	(d) LaBelle, E. V.; Marshall, C. W.; May, H. D. Acc. Chem. Res. 2020, 53, 62. doi: 10.1021/acs.accounts.9b00522 pmid: 24500279
[4]	Zhang, X.; Cui, T.; Zhao, X.; Liu, P.; Sun, P. Angew. Chem., Int. Ed. 2020, 59, 3465. doi: 10.1002/anie.201913332
[5]	Huang, Y.; Hong, H.; Zou, Z.; Liao, C.; Lu, J.; Qin, Y.; Li, Y.; Chen, L. Org. Biomol. Chem. 2019, 17, 5014. doi: 10.1039/C9OB00717B
[6]	Jud, W.; Kappe, C. O.; Cantillo, D. Chem.-Eur. J. 2018, 24, 17234. doi: 10.1002/chem.201804708
[7]	Zhang, L.; Zhang, G.; Wang, P.; Li, Y.; Lei, A. Org. Lett. 2018, 20, 7396. doi: 10.1021/acs.orglett.8b03081
[8]	Siu, J. C.; Sauer, G. S.; Saha, A.; Macey, R. L.; Fu, N. K.; Chauviré, T.; Lancaster, K. M.; Lin, S. J. Am. Chem. Soc. 2018, 140, 12511. doi: 10.1021/jacs.8b06744
[9]	Xu, H. H.; Song, J.; Xu, H. C. ChemSusChem 2019, 12, 3060. doi: 10.1002/cssc.201803058
[10]	Yuan, Y.; Cao, Y.; Lin, Y.; Li, Y.; Huang, Z.; Lei, A. ACS Catal. 2018, 8, 10871. doi: 10.1021/acscatal.8b03302
[11]	Kong, X.; Yu, K.; Chen, Q.; Xu, B. Asian J. Org. Chem. 2020, 9, 1. doi: 10.1002/ajoc.201900679
[12]	Zheng, M. W.; Yuan, X.; Cui, Y. S.; Qiu, J. K.; Li, G. G.; Guo, K. Org. Lett. 2018, 20, 7784. doi: 10.1021/acs.orglett.8b03191
[13]	Zhang, Z. F.; Yan, J. Y.; Ma, D. K.; Sun, J. W. Chin. Chem. Lett. 2019, 30, 1509. doi: 10.1016/j.cclet.2019.04.023
[14]	Mei, H. B.; Liu, J.; Guo, Y. J.; Han, J. L. ACS Omega 2019, 4, 14353. doi: 10.1021/acsomega.9b02442
[15]	Luo, M.-J.; Liu, B.; Li, Y.; Hu, M.; Li, J.-H. Adv. Synth. Catal. 2019, 361, 1538. doi: 10.1002/adsc.201801492
[16]	Gao, Y. Y.; Mei, H. B.; Han, J. L.; Pan, Y. Chem.-Eur. J. 2018, 24, 17205. doi: 10.1002/chem.201804157
[17]	Sun, X.; Ma, H. X.; Mei, T. S.; Fang, P.; Hu, Y. Org. Lett. 2019, 9, 3167.
[18]	Dai, C. H.; Shen, Y. J.; Wei, Y. F.; Liu, P.; Sun, P. P. J. Org. Chem. 2021, 86, 13711. doi: 10.1021/acs.joc.1c01831
[19]	Xiong, P.; Long, H.; Song, J.; Wang, Y.; Li, J. F.; Xu, H.-C. J. Am. Chem. Soc. 2018, 140, 16387. doi: 10.1021/jacs.8b08592 pmid: 30384602
[20]	Zhang, S.; Li, L.; Wu, P.; Gong, P.; Liu, R.; Xu, K. Adv. Synth. Catal. 2019, 361, 485. doi: 10.1002/adsc.201801173
[21]	Zhang, X.; Cui, T.; Zhao, X.; Liu, P.; Sun, P. Angew. Chem., Int. Ed. 2020, 59, 3465. doi: 10.1002/anie.201913332
[22]	Fu, N.; Sauer, G. S.; Saha, A.; Loo, A.; Lin, S. Science 2017, 357, 575. doi: 10.1126/science.aan6206
[23]	Fu, N.; Sauer, G. S.; Lin, S. J. Am. Chem. Soc. 2017, 139, 15548. doi: 10.1021/jacs.7b09388
[24]	Fu, N.; Shen, Y.; Allen, A. R.; Song, L.; Ozaki, A.; Lin, S. ACS Catal. 2019, 9, 746. doi: 10.1021/acscatal.8b03209
[25]	Fu, N. K.; Song, L.; Liu, J. J.; Shen, Y. F.; Siu, J. C.; Lin, S. J. Am. Chem. Soc. 2019, 141, 14480. doi: 10.1021/jacs.9b03296
[26]	Sun, X.; Ma, H.-M.; Mei, T.-S.; Fang, P.; Hu, Y.-L. Org. Lett. 2019, 21, 3167. doi: 10.1021/acs.orglett.9b00867
[27]	Cai, C.-Y.; Zheng, Y.-T.; Li, J.-F.; Xu, H.-C. J. Am. Chem. Soc. 2022, 144, 11980. doi: 10.1021/jacs.2c05126
[28]	Wu, H.; Chen, W.; Deng, W.; Yang, L.; Li, X.; Hu, Y.; Li, Y.; Chen, L.; Huang, Y. Org. Lett. 2022, 24, 1412. doi: 10.1021/acs.orglett.2c00314
[29]	Zhang, S.; Gao, W.; Shi, J.; Li, J.; Li, F.; Liang, Y.; Zhan, X.; Li, M.-B. Org. Chem. Front. 2022, 9, 1261 doi: 10.1039/D1QO01852C
[30]	Liu, J.; Xu, J.; Mei, H.; Han, J. Green Chem. 2022, 24, 6113. doi: 10.1039/D2GC01909D
[31]	Zhou, Pan.; Niu, K.; Song, H.; Liu, Y.; Wang, Q. Green Chem. 2022, 24, 5760 doi: 10.1039/D2GC02134J
[32]	Kong, X.; Chen, X.; Chen, Y.; Cao, Z.-Y. J. Org. Chem. 2022, 87, 7013. doi: 10.1021/acs.joc.1c03134
[33]	Tan, Z.; Xiang, F.; Xu, Kun.; Zeng, C. Org. Lett. 2022, 24, 5345. doi: 10.1021/acs.orglett.2c01983
[34]	Liang, S.; Zeng, C.-C.; Luo, X.-G.; Ren, F.-Z.; Tian, H.-Y.; Sun, B.-G.; Little, R. D. Green Chem. 2016, 18, 2222. doi: 10.1039/C5GC02626A
[35]	Yan, W.-Q.; Lin, M.-Y.; Little, R. D.; Zeng, C.-C. Tetrahedron 2017, 73, 764. doi: 10.1016/j.tet.2016.12.058
[36]	Doobary, S.; Sedikides, A. T.; Caldora, H. P.; Poole, D. L.; Lennox, A. J. J. Angew. Chem., Int. Ed. 2020, 59, 1155. doi: 10.1002/anie.201912119
[37]	Yang, D.; Yan, Q.; Zhu, E.; Lv, J.; He, W. Chin. Chem. Lett. 2022, 33, 1798. doi: 10.1016/j.cclet.2021.09.068
[38]	Pan, Y. Z.; Meng, X. J.; Cheng, S.-Y.; Li, Q. Y.; Tang, H. T.; Pan, Y. M. Synlett 2021, 32, 593. doi: 10.1055/a-1335-7902
[39]	(a) Mo, Z. Y.; Zhang, Y. Z.; Huang, G. B.; Wang, X. Y.; Tang, H. T. Adv. Synth. Catal. 2020, 362, 2160. doi: 10.1002/adsc.201901607
	(b) Cheng, S. Y.; Ou, C. H.; Lin, H. M.; Jia, J. S.; Tang, H.T.; Pan, Y. M.; Huang, G. B.; Meng, X. J. Chin. J. Org. Chem. 2021, 41, 4718. (in Chinese) doi: 10.6023/cjoc202110019
	( 程诗砚, 欧楚鸿, 林洪敏, 贾均松, 唐海涛, 潘英明, 黄国保, 蒙秀金, 有机化学, 2021, 41, 4718.) doi: 10.6023/cjoc202110019
[40]	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
[41]	Zhang, W.; Lin, S. J. Am. Chem. Soc. 2020, 49, 20661.
[42]	(a) Shatskiy, A.; Lundberg, H.; Kärkäs, M. D. ChemElectroChem 2019, 6, 4067. doi: 10.1002/celc.201900435
	(b) Poizot, P.; Gaubicher, J.; Renault, S.; Dubois, L.; Liang, Y.; Yao, Y. Chem. Rev. 2020, 14, 6490.
	(c) Martins, G. M.; Zimmer, G. C.; Mendes, S. R.; Ahmed, N. Green Chem. 2020, 22, 4849. doi: 10.1039/D0GC01324B
[43]	Zhu, L.; Xiong, P.; Mao, Z.-Y.; Wang, Y.-H.; Yan, X.; Lu, X.; Xu, H.-C. Angew. Chem., Int. Ed. 2016, 55, 2226. doi: 10.1002/anie.201510418
[44]	Xu, H. C.; Campbell, J. M.; Moeller, K. D. J. Org. Chem. 2014, 79, 379. doi: 10.1021/jo402623r
[45]	Tang, S.; Gao, X.; Lei, A. Chem. Commun. 2017, 53, 3354. doi: 10.1039/C7CC00410A
[46]	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
[47]	Zhong, P. F.; Lin, H. M.; Wang, L. W.; Mo, Z. Y.; Meng, X. J.; Tang, H. T.; Pan, Y. M. Green Chem. 2020, 22, 6334. doi: 10.1039/D0GC02125C
[48]	Meng, X. J.; Zhong, P. F.; Wang, Y. M.; Wang, H. S.; Tang, H. T.; Pan, Y. M. Adv. Synth. Catal. 2020, 362, 506. doi: 10.1002/adsc.201901115
[49]	Kharma, A.; Jacob, Cl.; Bozzi, Í. A. O.; Jardim, G. A. M.; Braga, A. L.; Salomão, K.; Gatto, C. C.; Silva, M. F. S.; Pessoa, C.; Stangier, M.; Ackermann, L.; Júnior, E. N. S. Eur. J. Org. Chem. 2020, 29, 4474.
[50]	Ye, K. Y.; Song, Z.; Sauer, G. S.; Harenberg, J. H.; Fu, N.; Lin, S. Chem.-Eur. J. 2018, 24, 12274. doi: 10.1002/chem.201802167
[51]	He, T.-J.; Zhong, W.-Q.; Huang, J.-M. Chem. Commun. 2020, 56, 2735. doi: 10.1039/C9CC09551A
[52]	Jiang, Y.-Y.; Dou, G.-Y.; Xu, K.; Zeng, C.-C. Org. Chem. Front. 2018, 5, 2573. doi: 10.1039/C8QO00645H
[53]	Zhang, Z.; Zhang, L.; Cao, Y.; Li, F.; Bai, G.; Liu, G.; Yang, Y.; Mo, F. Org. Lett. 2019, 21, 762. doi: 10.1021/acs.orglett.8b04010
[54]	Claraz, A.; Courant, T.; Masson, G. Org. Lett. 2020, 22, 1580. doi: 10.1021/acs.orglett.0c00176
[55]	Li, Z.; Jiao, L.; Sun, Y.; He, Z.; Wei, Z.; Liao, W. Angew. Chem., Int. Ed. 2020, 59, 7266. doi: 10.1002/anie.202001262
[56]	Zhang, S.; Li, L. J.; Zhang, J. J.; Zhang, J. Q.; Xue, M. Y.; Xu, K. Chem. Sci. 2019, 10, 3181. doi: 10.1039/C9SC00100J
[57]	Kang, J.-C.; Tu, Y.-Q.; Dong, J.-W.; Chen, C.; Zhou, J.; Ding, T.-M.; Zai, J.-T.; Chen, Z.-M.; Zhang, S.-Y. Green Chem. 2020, 22, 16. doi: 10.1039/C9GC03290H
[58]	Yang, J.; Li, G.; Yu, Ke.; Xu, Bo.; Chen, Q. J. Org. Chem. 2022, 87, 1208. doi: 10.1021/acs.joc.1c02557
[59]	Yang, F.; Nie, Y.-C.; Liu, H.-Y. Zhang, L.; Mo, F.; Zhu, R. ACS Catal. 2022, 12, 2132. doi: 10.1021/acscatal.1c05557
[60]	Hou, Z. W.; Mao, Z. Y.; Song, J.; Xu, H. C. ACS Catal. 2017, 7, 5810. doi: 10.1021/acscatal.7b02105
[61]	Xiong, P.; Xu, H. H.; Song, J.; Xu, H. C. J. Am. Chem. Soc. 2018, 140, 2460. doi: 10.1021/jacs.8b00391 pmid: 29406700
[62]	Hou, Z. W.; Mao, Z. Y.; Melcamu, Y. Y.; Lu, X.; Xu, H. C. Angew. Chem., Int. Ed. 2018, 57, 1636. doi: 10.1002/anie.201711876
[63]	Hou, Z.-W.; Mao, Z.-Y.; Zhao, H.-B.; Melcamu, Y. Y.; Lu, X.; Song, J.; Xu, H.-C. Angew. Chem., Int. Ed. 2016, 55, 9168. doi: 10.1002/anie.201602616
[64]	Xu, F.; Long, H.; Song, J.; Xu, H. Angew. Chem., Int. Ed. 2019, 58, 9017. doi: 10.1002/anie.201904931
[65]	Hou, Z.-W.; Xu, H.-C. Chin. J. Chem. 2020, 38, 394. doi: 10.1002/cjoc.201900500
[66]	Wen, J.; Shi, W.; Zhang, F.; Liu, D.; Tang, S.; Wang, H.; Lin, X. M.; Lei, A. Org. Lett. 2017, 19, 3131. doi: 10.1021/acs.orglett.7b01256
[67]	Wang, L. W.; Feng, Y. F.; Lin, H. M.; Tang, H. T.; Pan, Y. M.; J. Org. Chem. 2021, 22, 16121.
[68]	Hua, J.; Fang, Z.; Xu, J.; Bian, M.; Liu, C. K.; He, W.; Zhu, N.; Yang, Z.; Guo, K. Green Chem. 2019, 21, 4706. doi: 10.1039/C9GC02131K
[69]	Cai, C.; Lu, Y.; Yuan, C.; Fang, Z.; Yang, X.; Liu, C.; Guo, K. ACS Sustainable Chem. Eng. 2022, 10, 3288. doi: 10.1021/acssuschemeng.1c07933
[70]	Li, J.; Huang, W.; Chen, J.; He, L.; Cheng, X.; Li, G. Angew. Chem., Int. Ed. 2018, 20, 5695.
[71]	Cai, C. Y.; Xu, H. C. Nat. Commun. 2018, 9, 3551. doi: 10.1038/s41467-018-06020-8
[72]	Tang, S.; Wang, D.; Liu, Y.; Zeng, L.; Lei, A. Nat. Commun. 2018, 9, 798. doi: 10.1038/s41467-018-03246-4
[73]	Huang, P.; Wang, P.; Wang, S.; Tang, S.; Lei, A. Green Chem. 2018, 20, 4870. doi: 10.1039/C8GC02463D
[74]	Teng, Q. H.; Sun, Y.; Yao, Y.; Tang, H. T.; Li, J. R.; Pan, Y. M. ChemElectroChem 2019, 6, 3120. doi: 10.1002/celc.201900682
[75]	Xiong, T.-K.; Zhou, X.-Qi.; Zhang, M.; Tang, H.-T.; Pan, Y.-M.; Liang, Y. Green Chem. 2021, 23, 4328. doi: 10.1039/D1GC00949D
[76]	Tian, C.; Massignan, L.; Meyer, T. H.; Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 2383. doi: 10.1002/anie.201712647
[77]	Mei, R.; Sauermann, N.; Oliveira, J. C. A.; Ackermann, L. J. Am. Chem. Soc. 2018, 140, 7913. doi: 10.1021/jacs.8b03521
[78]	Kong, W.-J.; Shen, Z. G.; Finger, L. H.; Ackermann, L. Angew. Chem., Int. Ed. 2020, 59, 5551. doi: 10.1002/anie.201914775
[79]	Qiu, Y. A.; Tian, C.; Massignan, L.; Rogge, T.; Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 5818. doi: 10.1002/anie.201802748
[80]	Mei, R.; Koeller, J.; Ackermann, L. Chem. Commun. 2018, 54, 12879. doi: 10.1039/C8CC07732K
[81]	Xu, F.; Huang, Y.-J.; Li, C.; Xu, H.-C. ACS Catal. 2018, 8, 3820. doi: 10.1021/acscatal.8b00373
[82]	Luo, M. J.; Zhang, T. T.; Cai, F. J.; Li, J. H.; He, D. L. Chem. Commun. 2019, 55, 7251. doi: 10.1039/C9CC03210J
[83]	He, M. X.; Mo, Z. Y.; Wang, Z. Q.; Cheng, S. Y.; Xie, R. R.; Tang, H. T.; Pan, Y. M. Org. Lett. 2020, 22, 724. doi: 10.1021/acs.orglett.9b04549
[84]	Li, Q. Y.; Cheng, S. Y.; Tang, H. T.; Pan, Y. M. Org. Lett. 2019, 21, 9841. doi: 10.1021/acs.orglett.9b03682
[85]	Wang, Z.-Q.; Hou, C.; Zhong, Y.-F.; Lu, Y.-X.; Mo, Z.-Y.; Pan, Y.-M.; Tang, H.-T. Green Chem. 2019, 21, 5517. doi: 10.1039/C9GC03028J
[86]	Hu, X.; Nie, L.; Zhang, G.; Lei, A. Angew. Chem., Int. Ed. 2020, 25, 15238.
[87]	Cai, C.; Lu, Y.; Yuan, C.; Fang, Z.; Yang, X.; Liu, C.; Guo, K. ACS Sustainable Chem. Eng. 2021, 9, 16989. doi: 10.1021/acssuschemeng.1c05810
[88]	Mo, Z.-Y.; Swaroop, T. R.; T, Wei.; Zhang, Y. Z.; Tang, H. T.; Pan, Y. M.; Sun, H. B.; Chen, Z.-F. Green Chem. 2018, 20, 4428. doi: 10.1039/C8GC02143K
[89]	Wang, Z. Q.; Meng, X. J.; Li, Q. Y.; Tang, H. T.; Wang, H. S.; Pan, Y. M. Adv. Synth. Catal. 2018, 360, 4043. doi: 10.1002/adsc.201800871

电化学促进的烯烃和炔烃双官能团化反应研究进展

Recent Progress on the Electrochemical Difunctionalization of Alkenes/Alkynes

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