Visible Light-Induced Radical Cyclization for the Construction of 4-Aryl-1,2-dihydronaphthalenes

doi:10.6023/cjoc202302005

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3277-3286.DOI: 10.6023/cjoc202302005 Previous Articles Next Articles

可见光诱导的自由基环化反应构建4-芳基-1,2-二氢萘类化合物

樊思捷^a^,^b, 董武恒^a^,^b^,^*(), 梁彩云^b, 王贵超^a^,^b, 袁瑶^c, 尹作栋^a^,^*(), 张兆国^c^,^*()

a 广西大学化学化工学院广西南宁 530004
b 广西科技大学医学部广西柳州 545006
c 上海交通大学化学化工学院上海 200240

收稿日期:2023-02-05 修回日期:2023-04-20 发布日期:2023-05-05
基金资助:
广西科技大学人才启动基金(03190285); 广西科技基地与人才专项基金(桂科AD20238008)

Visible Light-Induced Radical Cyclization for the Construction of 4-Aryl-1,2-dihydronaphthalenes

Sijie Fan^a^,^b, Wuheng Dong^a^,^b(), Caiyun Liang^b, Guichao Wang^a^,^b, Yao Yuan^c, Zuodong Yin^a(), Zhaoguo Zhang^c()

a School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004
b Medicine Center, Guangxi University of Science and Technology, Liuzhou, Guangxi 545006
c School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received:2023-02-05 Revised:2023-04-20 Published:2023-05-05
Contact: * E-mail: wuheng190429@gxust.edu.cn;yinzhuod@gxu.edu.cn;zhaoguo@sjtu.edu.cn
Supported by:
Start-Up Funding from Guangxi University of Science and Technology(03190285); Guangxi Science and Technology Base and Talent Special Project Fund (AD20238008)

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Abstract

An efficient visible light-induced radical tandem cyclization method for the synthesis of 4-aryl-1,2-dihydronaph- thalenes is reported. The target products were obtained by the radical tandem cyclization of different types of monosubstituted aryl acetylenes with simple bromomalonates as radical precursors. Compared to conventional nucleophilic addition reactions, the method was obtained under mild conditions by irradiation with 7 W blue light at room temperature using fac-Ir(ppy)₃ as a photocatalyst. The reaction conditions are mild and the post-treatment is simple. This free radical triggered tandem cyclisation avails readily available bromomalonate esters and aryl alkynes as the starting materials. The method is very suitable for a wide range of substrates with good applicability to different bromomalonates and different alkynes.

Key words: visible light-induction, 4-aryl-1,2-dihydronaphthalenes, free radical tandem cyclisation

Cite this article

Sijie Fan, Wuheng Dong, Caiyun Liang, Guichao Wang, Yao Yuan, Zuodong Yin, Zhaoguo Zhang. Visible Light-Induced Radical Cyclization for the Construction of 4-Aryl-1,2-dihydronaphthalenes[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3277-3286.

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References 26

[1]	Walkinshaw A. J.; Xu W.; Suero M. G.; Gaunt M. J. J. Am. Chem. Soc. 2013, 135, 12532. doi: 10.1021/ja405972h pmid: 23947578
[2]	Bering L.; Jeyakumar K.; Antonchick A. P. Org. Lett. 2018, 20, 3911. doi: 10.1021/acs.orglett.8b01495 pmid: 29902015
[3]	Navaratne P. V.; Grenning A. J. Org. Biomol. Chem. 2017, 15, 69. doi: 10.1039/C6OB02250B
[4]	Xiao J.; Cong X. W.; Yang G. Z.; Wang Y. W.; Peng Y. Org. Lett. 2018, 20, 1651. doi: 10.1021/acs.orglett.8b00408
[5]	Charlton J. L.; Oleschuk C. J.; Chee G.-L. J. Org. Chem. 1996, 61, 3452. doi: 10.1021/jo952048e
[6]	Tian G.; Fedoseev P.; Van der Eycken E. V. Chem.-Eur. J. 2017, 23, 5224. doi: 10.1002/chem.v23.22
[7]	Lei C.; Yip Y. J.; Zhou J. S. J. Am. Chem. Soc. 2017, 139, 6086. doi: 10.1021/jacs.7b02742
[8]	Stavber G.; Zupan M.; Stavber S. Tetrahedron Lett. 2006, 47, 8463.
[9]	Yue G. L.; Wei J. Y.; Qiu D.; Mo F.-Y. Acta Chim. Sinica 2022, 80, 956. (in Chinese) doi: 10.6023/A22030118
	(岳广禄, 魏婧瑶, 邱頔, 莫凡洋, 化学学报, 2022, 80, 956.) doi: 10.6023/A22030118
[10]	Martínez A. G.; Barcina J. O.; Colorado Heras M. D. R.; Fresno De Fresno Cerezo Á. Organometallics 2001, 20, 1020. doi: 10.1021/om000957a
[11]	Campagne J.-M.; Dal Zotto C.; Wehbe J.; Virieux D. Synlett 2008, 2033.
[12]	Cheng L.; Zhou Q. L. Acta Chim. Sinica 2020, 78, 1017. (in Chinese) doi: 10.6023/A20070335
	(程磊, 周其林, 化学学报, 2020, 78, 1017.) doi: 10.6023/A20070335
[13]	Qiu Z.; Xie Z. Angew. Chem., Int. Ed. 2009, 48, 5729. doi: 10.1002/anie.v48:31
[14]	Sun C. L.; Wang Y.; Zhou X.; Wu Z. H.; Li B. J.; Guan B. T.; Shi Z. J. Chem.-Eur. J. 2010, 20, 5844. doi: 10.1002/chem.201490078
[15]	Novikov R. A.; Borisov D. D.; Tarasova A. V.; Tkachev Y. V.; Tomilov Y. V. Angew. Chem., Int. Ed. 2018, 57, 10293. doi: 10.1002/anie.201803541 pmid: 29897640
[16]	(a) Prier C. K.; Rankic D. A.; MacMillan D. W. C. Chem. Rev. 2013, 113, 5322. doi: 10.1021/cr300503r
	(b) Fagnoni D. M.; Albini A. Chem. Soc. Rev. 2013, 42, 97. doi: 10.1039/C2CS35250H
[17]	(a) Fukuzumi S.; Ohkubo K. Org. Biomol. Chem. 2014, 12, 6059. doi: 10.1039/C4OB00843J
	(b) Furst L.; Narayanam J. M.; Stephenson C. R. Angew. Chem., Int. Ed. 2011, 50, 9655. doi: 10.1002/anie.201103145
	(c) Gu X.; Lu P.; Fan W.; Li P.; Yao Y. Org. Biomol. Chem. 2013, 11, 7088. doi: 10.1039/c3ob41600c
	(d) Hari D. P.; Schroll P.; König B. J. Am. Chem. Soc. 2012, 134, 2958. doi: 10.1021/ja212099r
	(e) Kalyani D.; McMurtrey K. B.; Neufeldt S. R.; Sanford M. S. J. Am. Chem. Soc. 2011, 133, 18566. doi: 10.1021/ja208068w
[18]	Deng G. B.; Wang Z. Q.; Xia J. D.; Qian P. C.; Song R. J.; Hu M.; Gong L. B.; Li J. H. Angew. Chem., Int. Ed. 2013, 52, 1535. doi: 10.1002/anie.201208380
[19]	Liu J.; Wei Y.; Shi M. Org. Chem. Front. 2021, 8, 94. doi: 10.1039/D0QO00853B
[20]	Dong W.; Yuan Y.; Gao X.; Keranmu M.; Li W.; Xie X.; Zhang Z. Org. Lett. 2018, 20, 5762. doi: 10.1021/acs.orglett.8b02463
[21]	Dong W.; Yuan Y.; Xie X.; Zhang Z. Org. Lett. 2020, 22, 528. doi: 10.1021/acs.orglett.9b04283
[22]	Dong W.; Yuan Y.; Liang C.; Wu F.; Zhang S.; Xie X.; Zhang Z. J. Org. Chem. 2021, 86, 3697. doi: 10.1021/acs.joc.0c02477
[23]	Citterio A.; Sebastiano R.; Maronati A.; Santi R.; Bergamini F. J. Chem. Soc., Chem. Commun. 1994, 1517.
[24]	Yuan Y.; Zhang S. Y.; Dong W. H.; Wu F.; Xie X. M.; Zhang Z. G. Adv. Synth. Catal. 2021, 363, 4216. doi: 10.1002/adsc.v363.17
[25]	(a) Huo H.; Shen X.; Wang C.; Zhang L.; Röse P.; Chen L. A.; Harms K.; Marsch M.; Hilt G.; Meggers E. Nature 2014, 515, 100. doi: 10.1038/nature13892 pmid: 23001000
	(b) Larraufie M. H.; Pellet R.; Fensterbank L.; Goddard J. P.; Lacote E.; Malacria M.; Ollivier C. Angew. Chem., Int. Ed. 2011, 50, 4463. doi: 10.1002/anie.201007571 pmid: 23001000
	(c) Neumann M.; Fuldner S.; Konig B.; Zeitler K. Angew. Chem., Int. Ed. 2011, 50, 951. doi: 10.1002/anie.v50.4 pmid: 23001000
	(d) Nguyen J. D.; D'Amato E. M.; Narayanam J. M. R.; Stephenson C. R. J. Nat. Chem. 2012, 4, 854. pmid: 23001000
[26]	(a) Nguyen J. D.; Tucker J. W.; Konieczynska M. D.; Stephenson C. R. J. J. Am. Chem. Soc. 2011, 133, 4160. doi: 10.1021/ja108560e pmid: 18772399
	(b) Nicewicz D. A.; MacMillan D. W. C. Science 2008, 322, 77. doi: 10.1126/science.1161976 pmid: 18772399

Entry	Photocatalyst	Base	Solvent	Yield^b/%
1	fac-Ir(ppy)₃	Na₂CO₃	DMA	37
2	fac-Ir(ppy)₃	K₂CO₃	DMA	43
3	fac-Ir(ppy)₃	Li₂CO₃	DMA	42
4	fac-Ir(ppy)₃	ⁱPr₂NEt	DMA	7
5	fac-Ir(ppy)₃	Pyridine	DMA	9
6	fac-Ir(ppy)₃		DMA	62
7	fac-Ir(ppy)₃		DMF	86 (85^c)
8	fac-Ir(ppy)₃		DMSO	72
9	fac-Ir(ppy)₃		MeOH	82
10	fac-Ir(ppy)₃		EtOH	74
11	fac-Ir(ppy)₃		ⁱPr₂OH	44
12	fac-Ir(ppy)₃		CH₃CN	11
13	fac-Ir(ppy)₃		DCE	6
14	fac-Ir(ppy)₃		THF	0
15^d	fac-Ir(ppy)₃		DMF	0
16^e	fac-Ir(ppy)₃		DMF	0

Entry	Photocatalyst	Base	Solvent	Yield^b/%
1	fac-Ir(ppy)₃	Na₂CO₃	DMA	37
2	fac-Ir(ppy)₃	K₂CO₃	DMA	43
3	fac-Ir(ppy)₃	Li₂CO₃	DMA	42
4	fac-Ir(ppy)₃	ⁱPr₂NEt	DMA	7
5	fac-Ir(ppy)₃	Pyridine	DMA	9
6	fac-Ir(ppy)₃		DMA	62
7	fac-Ir(ppy)₃		DMF	86 (85^c)
8	fac-Ir(ppy)₃		DMSO	72
9	fac-Ir(ppy)₃		MeOH	82
10	fac-Ir(ppy)₃		EtOH	74
11	fac-Ir(ppy)₃		ⁱPr₂OH	44
12	fac-Ir(ppy)₃		CH₃CN	11
13	fac-Ir(ppy)₃		DCE	6
14	fac-Ir(ppy)₃		THF	0
15^d	fac-Ir(ppy)₃		DMF	0
16^e	fac-Ir(ppy)₃		DMF	0

可见光诱导的自由基环化反应构建4-芳基-1,2-二氢萘类化合物

Visible Light-Induced Radical Cyclization for the Construction of 4-Aryl-1,2-dihydronaphthalenes

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