ICl-Catalyzed Csp2—H Selenation of Aminocoumarin Derivatives

doi:10.6023/cjoc202106055

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4378-4383.DOI: 10.6023/cjoc202106055 Previous Articles Next Articles

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ICl催化氨基香豆素衍生物C_sp2—H芳(烷)硒化反应研究

何树华, 张行, 吴红谕, 周诗雨, 肖垚, 游贤会, 陈锦杨^*()

长江师范学院化学化工学院重庆 408000

收稿日期:2021-06-29 修回日期:2021-07-30 发布日期:2021-08-17
通讯作者: 陈锦杨
基金资助:
重庆市基础前沿研究(Cstc2018jcyjAX0051); 重庆市教育委员会(KJQN202001415)

ICl-Catalyzed C_sp2—H Selenation of Aminocoumarin Derivatives

Shuhua He, Hang Zhang, Hongyu Wu, Shiyu Zhou, Yao Xiao, Xianhui You, Jinyang Chen()

Department of Chemistry and Chemical Engineering, Yangtze Normal University, Chongqing 408000

Received:2021-06-29 Revised:2021-07-30 Published:2021-08-17
Contact: Jinyang Chen
Supported by:
Basic Frontier Research Project of Chongqing(Cstc2018jcyjAX0051); Science and Technology Research Program of Chongqing Municipal Education Commission(KJQN202001415)

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Abstract

Owing to their special biological activities, organic selenium heterocyclic compounds have widely applications in organic chemistry and drug synthesis. A series of methods for the synthesis of organoselenide heterocyclic compounds have been reported, however, shortcomings still exist. In this paper, an effective method for the synthesis of 3-aryl(alkyl)selenylcoumarin derivatives via the ICl-catalyzed selenation of coumarins with diaryl(alkyl)diselenide at room temperature is reported. In addition, this method is also suitable for the construction of C_sp2—Se bonds of other heterocyclic compounds. Compared to previous methods, this method has the advantages of mild conditions and wide functional groups tolerance, providing a general pathway to organoselenide heterocyclic compounds.

Key words: Iodine cation-catalyzed selenation, Construction of C_sp2—Se, Heterocyclic compounds, Diaryl(alkyl)diselenides

Cite this article

Shuhua He, Hang Zhang, Hongyu Wu, Shiyu Zhou, Yao Xiao, Xianhui You, Jinyang Chen. ICl-Catalyzed C_sp2—H Selenation of Aminocoumarin Derivatives[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4378-4383.

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References 42

[1]	Chen, Z.; Bi, J.; Su, W. Chin. J. Chem. 2013, 31, 507. doi: 10.1002/cjoc.201201130
[2]	Zhang, J.; Tan, Y.; Li, G.; Chen, L.; Nie, M.; Wang, Z.; Ji, H. Molecules 2021, 26, 786. doi: 10.3390/molecules26040786
[3]	Annunziata, F.; Pinna, C.; Dallavalle, S.; Tamborini, L.; Pinto, A. Int. J. Mol. Sci. 2020, 21, 4618. doi: 10.3390/ijms21134618
[4]	Goud, N. S.; Kumar, P.; Bharath, R. D. Mini Rev. Med. Chem. 2020, 20, 1754. doi: 10.2174/1389557520666200510000718
[5]	Liu, X.-H.; Liu, H.-F.; Chen, J.; Yang, Y.; Song, B.-A.; Bai, L.-S.; Liu, J.-X.; Zhu, H.-L.; Qi, X.-B. Bioorg. Med. Chem. Lett. 2010, 20, 5705.
[6]	Zhang, Z.; Bai, Z.-W.; Ling, Y. Med. Chem. 2018, 27, 1198.
[7]	Luo, G.; MosesMuyaba, W.; Tang, Z.; Zhao, R.; Xu, Q.; You, Q.; Xiang, H. Bioorg. Med. Chem. 2017, 27, 867. doi: 10.1016/j.bmcl.2017.01.013
[8]	Aman, K. K. B.; Pushap, R.; Pooja, C.; Sanjay, K. M.; Savita, C.; Narinder, S.; Navneet, K. New J. Chem. 2020, 44, 3341. doi: 10.1039/C9NJ04805G
[9]	Chen, J.; Yu, Y.; Li, S.; Ding, W. Molecules 2016, 21, 1501. doi: 10.3390/molecules21111501
[10]	Hu, X.-L.; Xu, Z.; Liu, M.-L.; Feng, L.-S.; Zhang, G.-D. Curr. Top. Med. Chem. 2017, 17, 3219.
[11]	Wu, J.-S.; Liu, W.-M.; Zhuang, X.-Q.; Wang, F.; Wang, P.-F.; Tao, S.-L.; Zhang, X.-H.; Wu, S.-K.; Lee, S.-T. Org. Lett. 2007, 9, 33. doi: 10.1021/ol062518z
[12]	Bugaenko, D. I.; Karchava, A. V.; Yunusova, Z. A.; Yurovskaya, M. A. Chem. Heterocycl. Com. 2019, 55, 483.
[13]	Styliani Voutsadaki, G. K.; Tsikalas, E. K.; George E, F.; Haralambos, E. K. Chem. Commun. 2010, 46, 3292. doi: 10.1039/b926384e
[14]	Zhang, G.; Zheng, H.; Guo, M.; Du, L.; Liu, G.; Wang, P. App. Surf. Sci. 2016, 367, 167. doi: 10.1016/j.apsusc.2016.01.110
[15]	Katerinopoulos, H. E. Curr. Pharm. Des. 2004, 10, 3835. doi: 10.2174/1381612043382666
[16]	Li, H.; Cai, L.; Li, J.; Hu, Y.; Zhou, P.; Zhang, J. Dyes Pigm. 2011, 91, 309. doi: 10.1016/j.dyepig.2011.05.011
[17]	Maja, M.; Melita, L.; Marija, K. Curr. Org. Chem. 2020, 24, 4. doi: 10.2174/1385272824666200120144305
[18]	Anamika, D. U.; Ekta, N. J.; Shivali, S. Curr. Org. Chem. 2018, 22, 2509. doi: 10.2174/1385272822666181029102140
[19]	Yu, N.; Yuki, S.; Takamitsu, H.; Suguru, Y. Org. Lett. 2020, 22, 8505. doi: 10.1021/acs.orglett.0c03106
[20]	Shi, L.; Li, Z.-Q; Cui, X.-X; Zhu, T.; Pang, X.-J; Li, L.-H; Luo, D.-F; Liu, F.-F; Zhao, B.-Y; Long, Y.; Zhang, S.-Y. Chin. J. Org. Chem. 2020, 40, 1598. (in Chinese) doi: 10.6023/cjoc201911028
	(时蕾, 李子秋, 崔鑫鑫, 朱挺, 庞晓静, 李龙辉, 罗德福, 刘方芳, 赵冰玉, 龙跃, 张赛扬, 有机化学, 2020, 40, 1598.) doi: 10.6023/cjoc201911028
[21]	Vieira, B. M.; Thurow, S.; Costa, M. D.; Casaril, A. M.; Domingues, M.; Schumacher, R. F.; Perin, G.; Alves, D.; Savegnago, L.; Lenardao, E. J. Asian J. Org. Chem. 2020, 56, 179.
[22]	Chen, Z.; Lai, H.; Hou, L.; Chen, T. Chem. Commun. 2020, 56, 179. doi: 10.1039/C9CC07683B
[23]	Chen, J.-Y.; Hu, L.; Wang, H.-Y.; Tan, H.-H. 有机化学, 2020, 39, 2048. (in Chinese)
	(陈锦杨, 胡丽, 汪海英, 谭红绘, 有机化学, 2019, 39, 2048.) doi: 10.6023/cjoc201812045
[24]	Doering, M.; Ba, L. A.; Lilienthal, N.; Nicco, C.; Scherer, C.; Abbas, M.; Zada, A. A. P.; Coriat, R.; Burkholz, T.; Wessjohann, L.; Diederich, M.; Batteux, F.; Herling, M.; Jacob, C. J. Med. Chem. 2010, 53, 6954. doi: 10.1021/jm100576z pmid: 20836556
[25]	Banerjee, B.; Koketsu, M. C. Chem. Rev. 2017, 339, 104.
[26]	Taniguchi, N.; Onami, T. J. Org. Chem. 2004, 69, 915. pmid: 14750822
[27]	Yang, D.; Li, G.; Xing, C.; Cui, W.; Li, K.; Wei, W. Org. Chem. Front. 2018, 5, 2974. doi: 10.1039/C8QO00899J
[28]	Tang, S.; Zeng, L.; Lei, A. J. Am. Chem. Soc. 2018, 140, 13128. doi: 10.1021/jacs.8b07327
[29]	Sun, L.; Zhang, X.; Wang, C.; Teng, H.; Ma, J.; Hao, Z.; Jiang, C. Green Chem. 2019, 21, 2732. doi: 10.1039/C9GC00913B
[30]	Wu, Y.; Chen, J.-Y.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He, W.-M. Green Chem. 2021, 23, 3950. doi: 10.1039/D1GC00562F
[31]	Chen, J.-Y.; Zhong, C.-T.; Gui, Q.-W.; Zhou, Y.-M.; Fang, Y.-Y.; Liu, K.-J.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2021, 32, 475. doi: 10.1016/j.cclet.2020.09.034
[32]	Zhang, X.; Yang, C.; Gao, H.; Wang, L.; Guo, L.; Xia, W. Org. Lett. 2021, 23, 347.
[33]	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.
[34]	Li, X.-D.; Gao, Y.-T.; Sun, Y.-J.; Jin, X.-Y.; Wang, D.; Liu, L.; Cheng, L. Org. Lett. 2019, 21, 6643. doi: 10.1021/acs.orglett.9b02183
[35]	Chen, W.-Y.; Lu, J. Synlett 2005, 1337.
[36]	Kidwai, M.; Bansal, V.; Mothsra, P.; Saxena, S.; Somvanshi, R. K.; Dey, S.; Singh, T. P. J. Mol. Catal. A: Chem. 2007, 268, 76. doi: 10.1016/j.molcata.2006.11.054
[37]	Weng, Y.; Zhou, H.; Sun, C.; Xie, Y.; Su, W. J. Org. Chem. 2017, 82, 9047. doi: 10.1021/acs.joc.7b01515
[38]	Kommula, D.; Li, Q.; Ning, S.; Liu, W.; Wang, Q.; Zhao, Z.-K. Synth. Commun. 2020, 50, 1026. doi: 10.1080/00397911.2020.1728775
[39]	Ghosh, P.; Nandi, A. K.; Chhetri, G.; Das, S. J. Org. Chem. 2018, 83, 12411. doi: 10.1021/acs.joc.8b01426
[40]	Noikham, M.; Yotphan, S. Eur. J. Org. Chem. 2019, 16, 2759.
[41]	Zhu, Y.-Q.; He, J.-L.; Niu, Y.-X.; Kang, H.-Y.; Han, T.-F.; Li, H.-Y. J. Org. Chem. 2018, 83, 9958. doi: 10.1021/acs.joc.8b01361
[42]	Zhang, X.; Wang, C.; Jiang, H.; Sun, L. Chem. Commun. 2018, 54, 8781. doi: 10.1039/C8CC04543G

Entry	Cat. (mol%)	Solvent	Temp./℃	Time/h	Yield^b/%
1	ICl (50)	DMSO	r.t.	12	90
2	ICl (40)	DMSO	r.t.	12	90
3	ICl (30)	DMSO	r.t.	12	90
4	ICl (20)	DMSO	r.t.	12	90
5	ICl (10)	DMSO	r.t.	12	86
6	ICl (5)	DMSO	r.t.	12	63
7	I₂ (20)	DMSO	r.t.	12	62
8	None	DMSO	r.t.	12	N.D.^c
9	ICl (20)	DMF	r.t.	12	75
10	ICl (20)	DMA	r.t.	12	81
11 12 13 14 15 16	ICl (20) ICl (20) ICl (20) ICl (20) ICl (20) ICl (20)	THF Toluene DCM 1,4-Dioxane DMSO DMSO	r.t. r.t. r.t. r.t. 50 80	12 12 12 12 12 12	64 59 26 69 90 85
17	ICl (20)	DMSO	80	6	73
18	ICl (20)	DMSO	r.t.	16	90
19	ICl (20)	DMSO	r.t.	8	85
20^d	ICl (20)	DMSO	r.t.	12	90
21^e	ICl (20)	DMSO	r.t.	12	75

Entry	Cat. (mol%)	Solvent	Temp./℃	Time/h	Yield^b/%
1	ICl (50)	DMSO	r.t.	12	90
2	ICl (40)	DMSO	r.t.	12	90
3	ICl (30)	DMSO	r.t.	12	90
4	ICl (20)	DMSO	r.t.	12	90
5	ICl (10)	DMSO	r.t.	12	86
6	ICl (5)	DMSO	r.t.	12	63
7	I₂ (20)	DMSO	r.t.	12	62
8	None	DMSO	r.t.	12	N.D.^c
9	ICl (20)	DMF	r.t.	12	75
10	ICl (20)	DMA	r.t.	12	81
11 12 13 14 15 16	ICl (20) ICl (20) ICl (20) ICl (20) ICl (20) ICl (20)	THF Toluene DCM 1,4-Dioxane DMSO DMSO	r.t. r.t. r.t. r.t. 50 80	12 12 12 12 12 12	64 59 26 69 90 85
17	ICl (20)	DMSO	80	6	73
18	ICl (20)	DMSO	r.t.	16	90
19	ICl (20)	DMSO	r.t.	8	85
20^d	ICl (20)	DMSO	r.t.	12	90
21^e	ICl (20)	DMSO	r.t.	12	75

ICl催化氨基香豆素衍生物C_sp2—H芳(烷)硒化反应研究

ICl-Catalyzed C_sp2—H Selenation of Aminocoumarin Derivatives

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ICl催化氨基香豆素衍生物Csp2—H芳(烷)硒化反应研究

ICl-Catalyzed Csp2—H Selenation of Aminocoumarin Derivatives

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ICl催化氨基香豆素衍生物C_sp2—H芳(烷)硒化反应研究

ICl-Catalyzed C_sp2—H Selenation of Aminocoumarin Derivatives