Electrochemically Mediated Esterification of Aromatic Aldehydes with Aliphatic Alcohols via Anodic Oxidation

doi:10.6023/cjoc202110019

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4718-4724.DOI: 10.6023/cjoc202110019 Previous Articles Next Articles

Special Issue: 有机电合成虚拟专辑；绿色合成化学专辑；热点论文虚拟合集

ARTICLES

电化学介导的芳香醛和脂肪醇氧化酯化反应

程诗砚^a, 欧楚鸿^a, 林洪敏^a, 贾均松^a, 唐海涛^a, 潘英明^a^,^c, 黄国保^b^,^*(), 蒙秀金^a^,^*()

a 广西师范大学化学与药学学院省部共建药用资源化学与药物分子工程国家重点实验室广西桂林 541004
b 玉林师范学院化学与食品科学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
c 吉首大学化学与化工学院湖南吉首 416000

收稿日期:2021-10-14 修回日期:2021-12-08 发布日期:2021-12-15
通讯作者: 黄国保, 蒙秀金
基金资助:
广西自然科学基金(2021GXNSFBA196041); 广西农产资源化学与生物技术重点实验室开放课题基金(2020KF04); 武陵山地区民族药解析与创制湖南省工程实验室开放课题(hgxy2101)

Electrochemically Mediated Esterification of Aromatic Aldehydes with Aliphatic Alcohols via Anodic Oxidation

Shiyan Cheng^a, Chuhong Ou^a, Hongmin Lin^a, Junsong Jia^a, Haitao Tang^a, Yingming Pan^a^,^c, Guobao Huang^b(), Xiujin Meng^a()

a State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi 541004
b Key Laboratory of Agricultural Resources Chemistry and Biotechnology, College of Chemistry and Food Science, Yulin Normal University, Yulin, Guangxi 537000
c College of Chemistry and Chemical Engineering, Jishou University, Jishou, Hunan 416000

Received:2021-10-14 Revised:2021-12-08 Published:2021-12-15
Contact: Guobao Huang, Xiujin Meng
Supported by:
Guangxi Natural Science Foundation(2021GXNSFBA196041); Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology(2020KF04); Opening Project of Hunan Engineering Laboratory for Analysis and Drugs Development of Ethnomedicine in Wuling Mountains(hgxy2101)

1. .pdf(1127KB)

Abstract

A series of ester compounds were synthesized by direct oxidative coupling of aldehydes with alcohols. The electrosynthesis reaction can be carried out at room temperature without inert gas protection, external oxidants, N-heterocyclic carbene (NHC) catalyst and alkali (such as DBU (1,5-dizzabicyclo[5.4.0]undecen-5-ene)), etc. The oxidative esterification reaction processes in a simple and easily available undivided electrochemical cell and constant current mode. This protocol features mild reaction conditions, broad substrate scope, cheap and easily available starting materials, and simple operation, providing a new strategy for the green synthesis of ester compounds.

Key words: organic electrosynthesis, dehydrogenative coupling, esterification

Cite this article

Shiyan Cheng, Chuhong Ou, Hongmin Lin, Junsong Jia, Haitao Tang, Yingming Pan, Guobao Huang, Xiujin Meng. Electrochemically Mediated Esterification of Aromatic Aldehydes with Aliphatic Alcohols via Anodic Oxidation[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4718-4724.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

References 28

[1]	Hettikankanamalage, A. A.; Lassfolk, R.; Ekholm, F. S.; Leino, R.; Crich, D. Chem. Rev. 2020, 120, 7104. doi: 10.1021/acs.chemrev.0c00243 pmid: 32627532
[2]	Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations, John Wiley & Sons, Inc., New York, 1999.
[3]	Otera, J.; Nishikido, J. J. Am. Chem. Soc. 2010, 132, 9221.
[4]	Sable, V.; Shah, J.; Sharma, A.; Kapdi, A. R. Chem. Asian J. 2019, 14, 2639. doi: 10.1002/asia.v14.15
[5]	Endo, A.; Kuroda, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346. pmid: 1010803
[6]	(a) Liu, C.; Tang, S.; Zheng, L.; Liu, D.; Zhang, H.; Lei, A. Angew. Chem., Int. Ed. 2012, 51, 5662. doi: 10.1002/anie.201201960
	(b) Zhu, L.; Ren, X.; Yu, Y.; Ou, P.; Wang, Z.-X.; Huang, X. Org. Lett. 2020, 22, 2087. doi: 10.1021/acs.orglett.0c00579
	(c) Li, X.; Goh, T. W.; Li, L.; Xiao, C.; Guo, Z.; Zeng, X. C.; Huang, W. ACS Catal. 2016, 6, 3461. doi: 10.1021/acscatal.6b00397
	(d) Suzuki, K.; Yamaguchi, T.; Matsushita, K.; Iitsuka, C.; Miura, J.; Akaogi, T.; Ishida, H. ACS Catal. 2013, 3,1845. doi: 10.1021/cs4004084
	(e) Paul, B.; Khatun, R.; Sharma, S. K.; Adak, S.; Singh, G.; Das, D.; Siddiqui, N.; Bhandari, S.; Joshi, V.; Sasaki, T.; Bal, R. ACS Sustainable Chem. Eng. 2019, 7, 3982. doi: 10.1021/acssuschemeng.8b05291
	(f) Cheng, J.; Zhu, M.; Wang, C.; Li, J.; Jiang, X.; Wei, Y.; Tang, W.; Xue, D.; Xiao, J. Chem. Sci. 2016, 7, 4428. doi: 10.1039/C6SC00145A
[7]	(a) Sarkar, S. D.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2010, 132, 1190. doi: 10.1021/ja910540j pmid: 20055393
	(b) Liu, B.; Yan, J.; Huang, R.; Wang, W.; Jin, Z.; Zanoni, G.; Zheng, P.; Yang, S.; Chi, Y. R. Org. Lett. 2018, 20, 3447. doi: 10.1021/acs.orglett.8b01029 pmid: 20055393
	(c) Wu, Z.; Jiang, D.; Wang, J. Org. Chem. Front. 2019, 6, 688. doi: 10.1039/C8QO01420E pmid: 20055393
	(d) Carmine, G. D.; Ragno, D.; Massi, A.; D'Agostino, C. Org. Lett. 2020, 22, 4927. doi: 10.1021/acs.orglett.0c01188 pmid: 20055393
[8]	(a) Gaspa, S.; Porcheddu, A.; Luca, L. D. Org. Lett. 2015, 17, 3666. doi: 10.1021/acs.orglett.5b01579
	(b) Chun, S.; Chung, Y. K. Org. Lett. 2017, 19: 3787. doi: 10.1021/acs.orglett.7b01617
	(c) Mühldorf, B.; Wolf, R. ChemCatChem 2017, 9, 920. doi: 10.1002/cctc.v9.6
	(d) Kozlov, K. S.; Romashov, L. V.; Ananikov, V. P. Green Chem. 2019, 21, 3464. doi: 10.1039/C9GC00840C
[9]	(a) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230. doi: 10.1021/acs.chemrev.7b00397 pmid: 24500279
	(b) Moeller, K. D. Chem. Rev. 2018, 118, 4817. doi: 10.1021/acs.chemrev.7b00656 pmid: 24500279
	(c) Wiebe, A.; Gieshoff, T.; Möhle, S.; Rodrigo, E.; Zirbes, M.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2018, 57, 5594. doi: 10.1002/anie.201711060 pmid: 24500279
	(d) Francke, R.; Little, R. D. Chem. Soc. Rev. 2014, 43, 2492. doi: 10.1039/c3cs60464k pmid: 24500279
	(e) Yoshida, J.; Shimizu, A.; Hayashi, R. Chem. Rev. 2018, 118, 4702. doi: 10.1021/acs.chemrev.7b00475 pmid: 24500279
	(f) Tang, S.; Liu, Y.; Lei, A. Chem 2018, 4, 27. doi: 10.1016/j.chempr.2017.10.001 pmid: 24500279
	(g) Yuan, Y.; Lei, A. Acc. Chem. Res. 2019, 52, 3309. doi: 10.1021/acs.accounts.9b00512 pmid: 24500279
	(h) Xiong, P.; Xu, H.-C. Acc. Chem. Res. 2019, 52, 3339. doi: 10.1021/acs.accounts.9b00472 pmid: 24500279
	(i) Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118, 4485. doi: 10.1021/acs.chemrev.7b00271 pmid: 24500279
	(j) Zhou, Y.-J.; Zhao, Z.-H.; Zeng, L.; Li, L.; He, Y.-H.; Gu, L.-J. Chin. J. Org. Chem. 2021, 41, 1072. (in Chinese) doi: 10.6023/cjoc202007049 pmid: 24500279
	( 周娅琴, 赵志恒, 曾亮, 李鸣, 何永辉, 谷利军, 有机化学, 2021, 41, 1072.) doi: 10.6023/cjoc202007049 pmid: 24500279
	(k) Meng, Z.-Y.; Feng, C.-T.; Xu, K. Chin. J. Org. Chem. 2021, 41, 2535. (in Chinese) doi: 10.6023/cjoc202012013 pmid: 24500279
	( 蒙泽银, 冯承涛, 徐坤, 有机化学, 2021, 41, 2535.) doi: 10.6023/cjoc202012013 pmid: 24500279
	(l) Wu, M.; Yu, L.; Hou, H.-Q.; Chen, H.-Z.; Zhuang, Q.-L.; Zhou, S.-Y.; Lin, X.-Y. Chin. J. Org. Chem. 2021, 41, 2326. (in Chinese) doi: 10.6023/cjoc202012028 pmid: 24500279
	( 吴媚, 于玲, 侯慧青, 陈厚铮, 庄庆龙, 周孙英, 林小燕, 有机化学, 2021, 41, 2326.) doi: 10.6023/cjoc202012028 pmid: 24500279
	(m) Liu, W.-Q.; Yang, X.-L.; Tong, Z.-H.; Wu, L.-Z. Acta Chim. Sinica 2019, 77, 861. (in Chinese) doi: 10.6023/A19030077 pmid: 24500279
	( 刘文强, 杨修龙, 佟振合, 吴骊珠, 化学学报, 2019, 77, 861.) doi: 10.6023/A19030077 pmid: 24500279
	(n) Ma, Y.; Wu, S.; Jiang, S.; Xiao, F.; Deng, G.-J. Chin. J. Chem. 2021, 39, 3334. doi: 10.1002/cjoc.v39.12 pmid: 24500279
	(o) Yang, Z.; Yu, Y.; Lai, L.; Zhou, L.; Ye, K.; Chen, F.-E. Green Synth. Catal. 2021, 2, 19. pmid: 24500279
	(p) Chen, N.; Xu, H.-C. Green Synth. Catal. 2021, 2, 165. pmid: 24500279
	(q) 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. pmid: 24500279
	(r) Chen, J.-Y.; Wu, H.-Y.; Gui, Q.-W.; Yan, S.-S.; Deng, J.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. J. Catal. 2021, 42, 1445. doi: 10.1016/S1872-2067(20)63750-0 pmid: 24500279
[10]	Finney, E. E.; Ogawa, K. A.; Boydston, A. J. J. Am. Chem. Soc. 2012, 134, 12374. doi: 10.1021/ja304716r pmid: 22768916
[11]	Green, R. A.; Pletcher, D.; Leach, S. G.; Brown, R. C. D. Org. Lett. 2015, 17, 3290. doi: 10.1021/acs.orglett.5b01459
[12]	(a) 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
	(b) 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
	(c) Li, Q.-Y.; Cheng, S.-Y.; Tang, H.-T.; Pan, Y.-M. Green Chem. 2019, 21, 5517. doi: 10.1039/C9GC03028J
	(d) 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.v362.3
	(e) 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
	(f) 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
[13]	Sawamura, T.; Takahashi, K.; Inagi, S.; Fuchigami, T. Angew. Chem., Int. Ed. 2012, 51, 4413. doi: 10.1002/anie.201200438
[14]	Xie, C.; Lin, L., Huang, L.; Wang, Z.; Jiang, Z.; Zhang, Z.; Han, B. Nat. Commun. 2021, 12, 4823. doi: 10.1038/s41467-021-25118-0
[15]	Teng, B.; Shi, J.; Yao, C. Green Chem. 2018, 20, 2465. doi: 10.1039/C8GC00500A
[16]	Yu, D.; To, W.-P.; Tong, G. S. M.; Wu, L.-L.; Chan, K.-T.; Du, L.; Phillips, D. L.; Liu, Y.; Che, C.-M. Chem. Sci. 2020, 11, 6370. doi: 10.1039/D0SC01340D
[17]	Wang, L.; Neumann, H.; Spannenberg, A.; Beller, M. Chem. Commun. 2017, 53, 7469. doi: 10.1039/C7CC02828H
[18]	Yang, H. S.; Macha, L.; Ha, H.-J.; Yang, J. W. Org. Chem. Front. 2021, 8, 53. doi: 10.1039/D0QO01135E
[19]	Khosravi, K.; Khalaji, K.; Naserifar, S. J. Chin. Chem. Soc. 2017, 64, 303. doi: 10.1002/jccs.2017.64.issue-3
[20]	Yu, C.; Özkaya, B.; Patureau, F. W. Chem.-Eur. J. 2021, 27, 3682. doi: 10.1002/chem.v27.11
[21]	Lawson, J. R.; Wilkins, L. C.; Melen, R. L. Chem.-Eur. J. 2017, 23, 10997. doi: 10.1002/chem.201703109 pmid: 28686789
[22]	Veatch, A. M.; Alexanian, E. J. Chem. Sci. 2020, 11, 7210. doi: 10.1039/D0SC02178D
[23]	Bourne-Branchu, Y.; Gosmini, C.; Danoun, G. Chem.-Eur. J. 2017, 23, 10043. doi: 10.1002/chem.201702608 pmid: 28594064
[24]	Silva, A. T. M.; Pereira, V. V.; Takahashi, J. A.; Silva, R. R.; Duarte, L. P. Nat. Prod. Res. 2018, 32, 1714. doi: 10.1080/14786419.2017.1399380
[25]	Hoque, M. E.; Hassan, M. M. M.; Chattopadhyay, B. J. Am. Chem. Soc. 2021, 143, 5022. doi: 10.1021/jacs.0c13415
[26]	Rysak, V.; Dixit, R.; Trivelli, X.; Merle, N.; Agbossou-Niedercorn, F.; Kumar, V.; Michon, C. Cat. Sci. Technol. 2020, 10, 4586. doi: 10.1039/D0CY00775G
[27]	Rammurthy, B.; Peraka, S.; Vasu, A.; Sai, G. K.; Rohini, Y. D.; Narender, N. Asian J. Org. Chem. 2021, 10, 594. doi: 10.1002/ajoc.v10.3
[28]	Velasco, N.; Suárez, A.; Martínez-Lara, F.; Fernández-Rodríguez, M. Á.; Sanz, R.; Suárez-Pantiga, S. J. Org. Chem. 2021, 86, 7078. doi: 10.1021/acs.joc.1c00333

Entry	Electrolyte	Solvent	Current/ mA	Electrode	Yield^b/ %
1	LiClO₄	CH₃CN	5	RVC(+)ǁPt(–)	65
2	LiClO₄	CH₃CN	10	RVC(+)ǁPt(–)	92
3	LiClO₄	CH₃CN	15	RVC(+)ǁPt(–)	92
4	NH₄I	CH₃CN	10	RVC(+)ǁPt(–)	35
5	TBAI	CH₃CN	10	RVC(+)ǁPt(–)	30
6	TBAP	CH₃CN	10	RVC(+)ǁPt(–)	NR
7	LiClO₄	DMSO	10	RVC(+)ǁPt(–)	58
8	LiClO₄	DMF	10	RVC(+)ǁPt(–)	Trace
9	LiClO₄	DCE	10	RVC(+)ǁPt(–)	20
10	LiClO₄	CH₃CN	10	Pt(–)ǁRVC(+)	25
11	LiClO₄	CH₃CN	10	RVC(+)ǁFe(–)	30
12	LiClO₄	CH₃CN	10	RVC(+)ǁNi(–)	38
13	LiClO₄	CH₃CN	10	RVC(+)ǁC felt(–)	40
14	LiClO₄	CH₃CN	10	RVC(+)ǁRVC(–)	45
15	LiClO₄	CH₃CN	10	C(+)ǁPt(–)	85
16	LiClO₄	CH₃CN	10	Pt(+)ǁPt(–)	NR

Entry	Electrolyte	Solvent	Current/ mA	Electrode	Yield^b/ %
1	LiClO₄	CH₃CN	5	RVC(+)ǁPt(–)	65
2	LiClO₄	CH₃CN	10	RVC(+)ǁPt(–)	92
3	LiClO₄	CH₃CN	15	RVC(+)ǁPt(–)	92
4	NH₄I	CH₃CN	10	RVC(+)ǁPt(–)	35
5	TBAI	CH₃CN	10	RVC(+)ǁPt(–)	30
6	TBAP	CH₃CN	10	RVC(+)ǁPt(–)	NR
7	LiClO₄	DMSO	10	RVC(+)ǁPt(–)	58
8	LiClO₄	DMF	10	RVC(+)ǁPt(–)	Trace
9	LiClO₄	DCE	10	RVC(+)ǁPt(–)	20
10	LiClO₄	CH₃CN	10	Pt(–)ǁRVC(+)	25
11	LiClO₄	CH₃CN	10	RVC(+)ǁFe(–)	30
12	LiClO₄	CH₃CN	10	RVC(+)ǁNi(–)	38
13	LiClO₄	CH₃CN	10	RVC(+)ǁC felt(–)	40
14	LiClO₄	CH₃CN	10	RVC(+)ǁRVC(–)	45
15	LiClO₄	CH₃CN	10	C(+)ǁPt(–)	85
16	LiClO₄	CH₃CN	10	Pt(+)ǁPt(–)	NR

电化学介导的芳香醛和脂肪醇氧化酯化反应

Electrochemically Mediated Esterification of Aromatic Aldehydes with Aliphatic Alcohols via Anodic Oxidation

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 28

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yunzhe Zhong, Ying hen, Lei Yu, Hongwei Zhou. Electrochemical Mediated Esterification Reaction of Carboxylic Acids and Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2855-2863.
[2]	Yijun Shi, Xinyue Sun, Han Cao, Fusheng Bie, Jie Ma, Zhe Liu, Xingshun Cong. Thioesterification of Esters with Primary Aliphatic Thiols at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2499-2505.
[3]	Zehui Li, Haoyu Zou, Lincai Li, Yiling Zhao, Hongping Zhu. Synthesis and Propylene Oxide Carbonylation Hydroesterification Catalytic Property of N,O-Ligand Coordination Cobalt Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3907-3915.
[4]	Jiayi Zhao, Yicong Ge, Chuan He. Construction of Silicon-Stereogenic Center via Catalytic Asymmetric Si—H/X—H Dehydrogenative Coupling [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3352-3366.
[5]	Dongping Xu, Fei Huang, Lin Tang, Xinming Zhang, Wu Zhang. Visible Light-Induced Hydroxyalkylation of Heteroarenes with Aliphatic Alcohols [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1493-1500.
[6]	Binyang Jiang, Shi-Liang Shi. Recent Progress in Upgrading of Alcohol and Amine via Asymmetric Dehydrogenative Coupling [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3263-3279.
[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]	Peng Wang, Da Yang, Huan Liu. Recent Advances on Carbonylation of 1,3-Dienes [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3379-3389.
[9]	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.
[10]	Wanqun Tian, Mengyuan Li, Shuang Yang, Hao Zhang, Haiyang Liu, Xinyan Xiao. Copper Corrole as an Efficient Catalyst for Esterification of Allylic sp³-C—H Bonds with Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2875-2884.
[11]	Muxue He, Shiyan Cheng, Yongzhou Pan, Haitao Tang, Yingming Pan. Electrochemically Mediated S—N Bond Formation: Synthesis of Sulfenamides [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2354-2360.
[12]	Xiaoping Zhang, Guiyong Jin, Zhifei Chen, Qingfu Wang, Sensen Zhao, Zhiyong Wu, Shuai Wan, Gaolei Xi, Xu Zhao. Synthesis and Antioxidant Properties of Pyrazine-Thiazole Bi-heteroaryl Compounds [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2445-2453.
[13]	Hao Wang, Ping Ying, Jingbo Yu, Weike Su. Alternative Strategies Enabling Cross-Dehydrogenative Coupling: Access to C—C Bonds [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1897-1924.
[14]	Yu Jieqiang, Jia Jun, Wang Xingwang. Synthesis of a Type of Linear β,γ-Unsaturated α-Keto Tryptophol Ester Compounds [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2778-2787.
[15]	Wang Hui, Wang Anwei, Xia Zhenzhen, Zhou Weiyou, Sun Zhonghua, Qian Junfeng, He Mingyang. Nickel(Ⅱ)-Catalyzed Aerobic Cross-Dehydrogenative Coupling for the Synthesis of N-Aryl Tetrahydroisoquinolines [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2099-2107.