Electrochemistry-Enabled 2,2,6,6-Tetramethylpiperidoxyl (TEMPO)-Mediated Oxidative Dehydrogenation Povarov/Tandem Reactions of Glycine Derivatives

doi:10.6023/cjoc202401002

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (3): 940-950.DOI: 10.6023/cjoc202401002 Previous Articles Next Articles

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电化学促进2,2,6,6-四甲基哌啶氧化物(TEMPO)介导的甘氨酸衍生物氧化脱氢Povarov/串联反应

李章健^a^,^b, 王振华^b, 郭剑峰^b, 方萍^b, 马聪^b^,^*(), 刘润华^b^,^c^,^*(), 梅天胜^b^,^c^,^*()

a 四川师范大学化学与材料科学学院成都 610068
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室中国科学院大学上海 200032
c 中国科学院上海有机化学研究所宁波中科新材料创制中心浙江宁波 315800

收稿日期:2024-01-04 修回日期:2024-02-28 发布日期:2024-04-02
基金资助:
中国科学院战略性先导科技专项(XDB0610000); 国家重点研发项目(2021YFA1500100); 国家自然科学基金(21821002); 国家自然科学基金(91956112); 国家自然科学基金(22101294); 上海市科学技术委员会(21ZR1476500); 上海市科学技术委员会(20XD1425100); 宁波市自然科学基金(2023J035)

Electrochemistry-Enabled 2,2,6,6-Tetramethylpiperidoxyl (TEMPO)-Mediated Oxidative Dehydrogenation Povarov/Tandem Reactions of Glycine Derivatives

Zhang-Jian Li^a^,^b, Zhen-Hua Wang^b, Jian-Feng Guo^b, Ping Fang^b, Cong Ma^b(), Run-Hua Liu^b^,^c(), Tian-Sheng Mei^b^,^c()

a College of Chemistry and Materials, Sichuan Normal University, Chengdu 610068
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032
c Ningbo Zhongke Creation Center of New Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Ningbo, Zhejiang 315800

Received:2024-01-04 Revised:2024-02-28 Published:2024-04-02
Contact: *E-mail: mei7900@sioc.ac.cn; macong2016@sioc.ac.cn; liurh@mail.sioc.ac.cn
Supported by:
Strategic Priority Research Program of the Chinese Academy of Sciences(XDB0610000); National Key R&D Program of China(2021YFA1500100); National Natural Science Foundation of China(21821002); National Natural Science Foundation of China(91956112); National Natural Science Foundation of China(22101294); Science and Technology Commission of Shanghai Municipality of Shanghai(21ZR1476500); Science and Technology Commission of Shanghai Municipality of Shanghai(20XD1425100); Natural Science Foundation of Ningbo(2023J035)

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Abstract

The oxidative dehydrogenation Povarov/tandem reaction between electrochemically oxidized glycine derivatives and olefins was investigated. Specifically, a nitrogen oxide radical 2,2,6,6-tetramethylpiperidoxyl (TEMPO) was used as a redox mediator to reduce the potential of the electrochemical reaction and avoid over-oxidation of electron-rich aromatic amines at higher potentials. The reaction provides a potential pathway for the nitrogen-α functionalization of glycine derivatives. Further, the reaction represents an efficient method for synthesizing quinoline derivatives under mild conditions to achieve high yields through a combination of Shono oxidation and Povarov reactions.

Key words: electrochemistry, 2,2,6,6-tetramethylpiperidoxyl (TEMPO), Povarov reaction, Shono oxidation

Cite this article

Zhang-Jian Li, Zhen-Hua Wang, Jian-Feng Guo, Ping Fang, Cong Ma, Run-Hua Liu, Tian-Sheng Mei. Electrochemistry-Enabled 2,2,6,6-Tetramethylpiperidoxyl (TEMPO)-Mediated Oxidative Dehydrogenation Povarov/Tandem Reactions of Glycine Derivatives[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 940-950.

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Fig. & Tab. 9

References 11

[1]	(a) Ma C.; Fang P.; Mei T.-S. ACS Catal. 2018, 8, 7179. doi: 10.1021/acscatal.8b01697
	(b) Yuan Y.; Lei A. Acc. Chem. Res. 2019, 52, 3309. doi: 10.1021/acs.accounts.9b00512
	(c) Xiong P.; Xu H.-C. Acc. Chem. Res. 2019, 52, 3339. doi: 10.1021/acs.accounts.9b00472
	(d) Roeckl J. L.; Pollok D.; Franke R.; Waldvogel R. S. Acc. Chem. Res. 2020, 53, 45. doi: 10.1021/acs.accounts.9b00511
	(e) Zhu C.; Ang N. W. J.; Meyer T. H.; Qiu Y.; Ackermann L. ACS Cent. Sci. 2021, 7, 415. doi: 10.1021/acscentsci.0c01532
	(f) Malapit C.; Minteer S. D. Chem. Rev. 2022, 122, 3180. doi: 10.1021/acs.chemrev.1c00614
	(g) Zhang X.; Zhan J.; Yu Z.; Deng J.; Li M.; Shao Y. Chin. J. Chem. 2023, 41, 214. doi: 10.1002/cjoc.v41.2
	(h) Zeng L.; Qin J.-H.; Lv G.-F.; Hu M.; Sun Q.; Ouyang X.-H.; He D.-L.; Li J.-H. Chin. J. Chem. 2023, 41, 1921. doi: 10.1002/cjoc.v41.16
[2]	(a) Kingston C.; Palkowitz M. D.; Kawamata Y.; Baran P. S. Acc. Chem. Res. 2020, 53, 72. doi: 10.1021/acs.accounts.9b00539
	(b) Wang F.; Stahl S. Acc. Chem. Res. 2020, 53, 561. doi: 10.1021/acs.accounts.9b00544
	(c) Pollok D.; Waldvogel S. R. Chem. Sci. 2020, 11, 12386. doi: 10.1039/D0SC01848A
	(d) Siu J. C.; Fu N. K.; Lin S. Acc. Chem. Res. 2020, 53, 547. doi: 10.1021/acs.accounts.9b00529
	(e) Zhu C.; Ang N. W. J.; Meyer T.-H.; Qiu Y.; Ackermann L. ACS Cent. Sci. 2021, 7, 415. doi: 10.1021/acscentsci.0c01532
	(f) Wang Z.-H.; Ma C.; Fang P.; Xu H.-C.; Mei T.-S. Acta Chim. Sinica 2022, 80, 1115. (in Chinese) doi: 10.6023/A22060260
	( 王振华, 马聪, 方萍, 徐海超, 梅天胜, 化学学报, 2022, 80, 1115.)
	(g) Cheng X.; Lei A.; Mei T.-S.; Xu H.-C.; Xu K.; Zeng C. CCS Chem. 2022, 4, 1120. doi: 10.31635/ccschem.021.202101451
[3]	(a) Shono T.; Hamaguchi H.; Matsumura Y. J. Am. Chem. Soc. 1975, 97, 4264. doi: 10.1021/ja00848a020 pmid: 35015533
	(b) Shono T.; Matsumura Y.; Uchida K.; Tsubata K.; Makino A. J. Org. Chem. 1984, 49, 300. doi: 10.1021/jo00176a016 pmid: 35015533
	(c) Onomura O. Heterocycles 2012, 85, 2111. doi: 10.3987/REV-12-744 pmid: 35015533
	(d) Jones A. M.; Banks C. E. Beilstein J. Org. Chem. 2014, 10, 3056. doi: 10.3762/bjoc.10.323 pmid: 35015533
	(e) Fu N.; Li L.; Yang Q.; Luo S. Org. Lett. 2017, 19, 2122. doi: 10.1021/acs.orglett.7b00746 pmid: 35015533
	(f) Kärkäs M. D. Chem. Soc. Rev. 2018, 47, 5786. doi: 10.1039/C7CS00619E pmid: 35015533
	(g) Wang F.; Rafiee M.; Stahl S. S. Angew. Chem., Int. Ed. 2018, 57, 6686. doi: 10.1002/anie.v57.22 pmid: 35015533
	(h) Lennox A. J. J.; Goes S. L.; Webster M. P.; Koolman H. F.; Djuric S. W.; Stahl S. S. J. Am. Chem. Soc. 2018, 140, 11227. doi: 10.1021/jacs.8b08145 pmid: 35015533
	(i) Feng T.; Wang S.; Qiu Y. Synlett 2022, 33, 1582. doi: 10.1055/a-1828-1217 pmid: 35015533
	(j) Novaes L. F. T.; Ho J. S. K.; Mao K.; Liu K.; Tanwar M.; Neurock M.; Villemure E.; Terrett J. A.; Lin S. J. Am. Chem. Soc. 2022, 144, 1187. doi: 10.1021/jacs.1c09412 pmid: 35015533
[4]	(a) Povarov L, S.; Mikhailov B, M. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1963, 953.
	(b) Povarov L, S.; Mikhailov B, M. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1963, 2039.
	(c) Povarov L. S. Chem. Rev. 1967, 36, 656.
	(d) Makioka Y.; Shindo T.; Taniguchi Y.; Takaki K.; Fujiwara F. Synthesis 1995, 1995, 801. doi: 10.1055/s-1995-4002
	(e) Mariafrancesca F.; Lorenzo C.; Luca B. Synthesis 2014, 46, 135. doi: 10.1055/s-00000084
[5]	(a) Francke R.; Little R. D. Chem. Soc. Rev. 2014, 43, 2492. doi: 10.1039/c3cs60464k pmid: 24500279
	(b) Yan M.; Kawamata Y.; Baran P. S. Chem. Rev. 2017, 117, 13230. doi: 10.1021/acs.chemrev.7b00397 pmid: 24500279
	(c) Masdeu C.; Palacios F.; Alonso C. Top. Curr. Chem. 2023, 381, 20. pmid: 24500279
[6]	(a) Povarov L. S.; Mikhailov B. M.; Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1963, 953. pmid: 21718039
	(b) Murata S.; Miura M.; Nomura M. J. Org. Chem. 1989, 54, 4700. doi: 10.1021/jo00280a049 pmid: 21718039
	(c) Murahashi S, I.; Naota T.; Miyaguchi N.; Nakato T. Tetrahedron Lett. 1992, 33, 6991. doi: 10.1016/S0040-4039(00)60914-0 pmid: 21718039
	(d) Araneo S.; Fontana F.; Minisci F.; Recupero F.; Serri A. Tetrahedron Lett. 1995, 36, 4307. doi: 10.1016/0040-4039(95)00746-Y pmid: 21718039
	(e) Huang L. H.; Zhang X. B.; Zhang Y. H. Org. Lett. 2009, 11, 3730. doi: 10.1021/ol901347t pmid: 21718039
	(f) Nishino M.; Hirano K.; Satoh T.; Miura M. J. Org. Chem. 2011, 76, 6447. doi: 10.1021/jo2011329 pmid: 21718039
	(g) Zhu S, Q.; Das A.; Bui L.; Zhou H. J.; Curran D. P.; Rueping M. J. Am. Chem. Soc. 2013, 135, 1823. doi: 10.1021/ja309580a pmid: 21718039
	(h) Zhao L.; Baslø O.; Li C.-J. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 4106. doi: 10.1073/pnas.0809052106 pmid: 21718039
[7]	(a) Richter H.; García Mancheño O. Org. Lett. 2011, 13, 6066. doi: 10.1021/ol202552y pmid: 23705827
	(b) Rohlmann R.; Stopka T.; Richter H.; García Mancheño O. J. Org. Chem. 2013, 78, 6050. doi: 10.1021/jo4007199 pmid: 23705827
[8]	(a) Jia X.; Peng F.; Qing C.; Huo C.; Wang X. Org. Lett. 2012, 14, 4030. doi: 10.1021/ol301909g
	(b) Jia X.; Wang Y.; Peng F.; Huo C.; Yu L.; Liu J.; Wang X. J. Org. Chem. 2013, 78, 9450. doi: 10.1021/jo401018v
	(c) Liu P.; Wang Z.; Lin J.; Hu X. Eur. J. Org. Chem. 2012, 2012, 1583. doi: 10.1002/ejoc.v2012.8
	(d) Huo C.; Yuan Y.; Wu M.; Jia X.; Wang X.; Chen F.; Tang J. Angew. Chem., Int. Ed. 2014, 126, 13762. doi: 10.1002/ange.v126.49
	(e) Huo C.; Xie H, S.; Wu M, X.; Jia X, D.; Wang X.; Tang J. Chem.-Eur. J. 2015, 21, 5723. doi: 10.1002/chem.v21.15
[9]	(a) Xie Z. Y.; Jia J.; Liu X. G.; Liu L. Adv. Synth. Catal. 2016, 358, 919. doi: 10.1002/adsc.v358.6
	(b) Ni M.; Zhang Y.; Gong T.; Feng B. Adv. Synth. Catal. 2017, 359, 824. doi: 10.1002/adsc.v359.5
	(c) Yang X.; Li Y.; Li Y.; Zhang Y. J. Org. Chem. 2016, 81, 12433. doi: 10.1021/acs.joc.6b02683
	(d) Wang S.; Ye Y.; Hu Y.; Meng M.; Liu Z.; Liu J.; Chen K.; Zhang Z.; Zhang Y. Chem. Commun. 2023, 59, 2628. doi: 10.1039/D2CC07071E
[10]	(a) Wang Z.-H.; Gao P.-S.; Wang X.; Gao J.-Q.; Xu X.-T.; He Z.; Ma C.; Mei T.-S. J. Am. Chem. Soc. 2021, 143, 15599. doi: 10.1021/jacs.1c08671
	(b) Gao J.-Q.; Weng X.-J.; Ma C.; Xu X.-T.; Fang P.; Mei T.-S. Chin. J. Org. Chem. 2021, 41, 3223. (in Chinese)
	( 高君青, 翁信军, 马聪, 徐学涛, 方萍, 梅天胜, 有机化学, 2021, 41, 3223.)
	(c) Gao P.-S.; Weng X.-J.; Wang Z.-H.; Zheng C.; Sun B.; Chen Z.-H.; You S.-L.; Mei T.-S. Angew. Chem., Int. Ed. 2020, 59, 15254. doi: 10.1002/anie.v59.35
	(d) Liu H.-L.; He Z.; Wang N.-N.; Xu H.; Fang P.; Mei T.-S. Org. Lett. 2023, 25, 608. doi: 10.1021/acs.orglett.2c04136
	(e) He Z.; Liu H.-L.; Wang Z.-H.; Jiao K.-J.; Li Z.-M.; Li Z.-J.; Fang P.; Mei T.-S. J. Org. Chem. 2023, 88, 6203. doi: 10.1021/acs.joc.3c00223
[11]	(a) James M.; Ramesh V.; Claudia B.; Robert Y.; Lorraine J.-B. Org. Biomol. Chem. 2014, 12, 255. doi: 10.1039/C3OB41539B pmid: 19572501
	(b) Wang J.; Li L.; Guo Y.; Li S.; Wang S.; Li Y.; Zhang Y. Org. Biomol. Chem. 2020, 18, 8179. doi: 10.1039/D0OB01837F pmid: 19572501
	(c) Jaideep B.; Abubakar W.;Sadhana, S.; Imam, R, S.; Manoj, K.; Ram, A, V.; Ajay, K.; Sandip B. Org. Biomol. Chem. 2014, 12, 6267. doi: 10.1039/c4ob00488d pmid: 19572501
	(d) Heinrich R.; Mancheno G. Org. Lett. 2011, 13, 6066. doi: 10.1021/ol202552y pmid: 19572501
	(e) Yang X.; Li L.; Li Y.; Zhang Y. J. Org. Chem. 2016, 81, 12433. doi: 10.1021/acs.joc.6b02683 pmid: 19572501
	(f) Huang H.; Jiang H.; Chen K.; Liu H. J. Org. Chem. 2009, 74, 5476. doi: 10.1021/jo901101v pmid: 19572501

Entry	Variations from standard conditions	Yield^b/%
1	None	97 (95^c)^a
2	No Fe(OTf)₃	0
3	No TEMPO	43
4	No current	22
5	Under N₂	Trace
6	Ce(OTf)₃ instead of Fe(OTf)₃	41
7	Fe(OTf)₂ instead of Fe(OTf)₃	17
8	n-Bu₄NCl instead of n-Bu₄NPF₆	trace
9	Et₄NBF₄instead of n-Bu₄NPF₆	36
10	Carbon felt instead of RVC	43
11	DIPEA	trace
12	3.0 mA	24
13	4-OH-TEMPO instead of TEMPO	55
15	ABNO instead of TEMPO	68

Entry	Variations from standard conditions	Yield^b/%
1	None	97 (95^c)^a
2	No Fe(OTf)₃	0
3	No TEMPO	43
4	No current	22
5	Under N₂	Trace
6	Ce(OTf)₃ instead of Fe(OTf)₃	41
7	Fe(OTf)₂ instead of Fe(OTf)₃	17
8	n-Bu₄NCl instead of n-Bu₄NPF₆	trace
9	Et₄NBF₄instead of n-Bu₄NPF₆	36
10	Carbon felt instead of RVC	43
11	DIPEA	trace
12	3.0 mA	24
13	4-OH-TEMPO instead of TEMPO	55
15	ABNO instead of TEMPO	68

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电化学促进2,2,6,6-四甲基哌啶氧化物(TEMPO)介导的甘氨酸衍生物氧化脱氢Povarov/串联反应

Electrochemistry-Enabled 2,2,6,6-Tetramethylpiperidoxyl (TEMPO)-Mediated Oxidative Dehydrogenation Povarov/Tandem Reactions of Glycine Derivatives

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