Copper-Catalyzed Vicinal C(sp2)—H Selenylation of Benzoic Acid Derivatives Using Air as Oxidant

doi:10.6023/cjoc202102002

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2302-2309.DOI: 10.6023/cjoc202102002 Previous Articles Next Articles

Special Issue: 热点论文虚拟合集

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空气氧化的铜催化苯甲酸衍生物邻位C(sp²)—H键的硒化反应

孙名扬, 徐坤, 郭兵兵, 曾程初^*()

北京工业大学环境与生命学部北京 100124

收稿日期:2021-02-01 修回日期:2021-02-28 发布日期:2021-03-12
通讯作者: 曾程初
基金资助:
国家自然科学基金(21871019)

Copper-Catalyzed Vicinal C(sp²)—H Selenylation of Benzoic Acid Derivatives Using Air as Oxidant

Mingyang Sun, Kun Xu, Bingbing Guo, Chengchu Zeng()

Faculty of Enviroment and Life Science, Beijing University of Technology, Beijing 100124

Received:2021-02-01 Revised:2021-02-28 Published:2021-03-12
Contact: Chengchu Zeng
Supported by:
National Natural Science Foundation of China(21871019)

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Abstract

An efficient copper-catalyzed vicinal C(sp²)―H selenylation of benzoic acid dervatives is reported using diselenyl ether as selenyl resource, 8-aminoquinoline as the directing group. The protocol need only air as the terminal oxidant, avoiding the utilization of other external chemical oxidants, featuring good substrates generality and compatiblity of functional groups.

Key words: copper-catalyzed, C—H activation, selenylation reaction, diselenyl ether, 8-aminoquinoline

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Mingyang Sun, Kun Xu, Bingbing Guo, Chengchu Zeng. Copper-Catalyzed Vicinal C(sp²)—H Selenylation of Benzoic Acid Derivatives Using Air as Oxidant[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2302-2309.

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References 15

[3]	(b) Vanessa, G. R.; Camilo, S. F.; Gelson, P.; Eder, J. L.; Raquel, G. J.; Lucielli, S.; Diego, A. Green Chem. 2012, 14,1030.
[4]	(a) Michal, M.; Axel, J. W. Chem. Commun. 2013, 49,5507.
	(b) Nirmalya, M.; Tanmay, C.; Brindaban, C. R. J. Org. Chem. 2013, 78,11110.
[5]	(a) Prasad, C. D.; Shah, J. B.; Amit, K.; Bhagat, S. B.; Kaustubh, S.; Soumava, B.; Sangit, K. J. Org. Chem. 2013, 78,1434.
	(b) Vanessa, G. R.; Samuel, T.; Filipe, P.; Ricardo, F. S.; Gelson, P.; Eder, J. L.; Diego, A. Adv. Synth. Catal. 2015, 357,933.
	(c) Zhang, X.; Wang, C. G.; Jiang, H.; Sun, L. H. Chem. Commun. 2018, 54,8781.
	(d) Yeon, J. K.; Dae, Y. K. Tetrahedron Lett. 2019, 60,739.
[6]	(a) Sukalyan, B.; Amit, S.; Brindaban, C. R. J. Org. Chem. 2010, 75,4864.
	(b) Thurow, S.; Penteado, F.; Perin, G.; Jacob, R. G.; Alves, D.; Lenardao, E. J. Green Chem. 2014, 16,3854.
	(c) Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P. V. Tetrahedron Lett. 2003, 44,7039.
[7]	(a) Ren, P. X.; Qi, L.; Fang, Z. Y.; Wu, T. S.; Gao, Y. M.; Shen, S.; Song, J. Y.; Wang, L. J.; Li, W. Chin. J. Org. Chem. 2019, 39,1776(in Chinese).
	(任培星, 齐林, 方卓越, 吴天舒, 高雅蒙, 沈松, 宋金燕, 王力竞, 李玮, 有机化学, 2019, 39,1776.)
	(b) Wang, X.; Mu, S. Q.; Sun, T.; Sun, K. Chin. J. Org. Chem. 2019, 39,2802(in Chinese).
	(王薪, 穆石强, 孙婷, 孙凯, 有机化学, 2019, 39,2802.)
	(c) Sun, K.; Wang, S. N.; Feng, R. R.; Zhang, Y. X.; Wang, X.; Zhang, Z. G.; Zhang, B. Org. Lett. 2019, 21,2052.
	(d) Wang, X.; Wang, Q. L.; Xue, Y. R.; Sun, K.; Wu, L. L.; Zhang, B. Chem. Commun. 2020, 56,4436.
	(e) Sun, K.; Wang, X.; Li, C.; Wang, H.; Li, L. Org. Chem. Front. 2020, 7,3100.
[8]	(a) Guy, R.; Naoto, C. Angew. Chem., Int. Ed. 2013, 52,11726.
	(b) Supriya, R.; Yusuke, A.; Naoto, C. Chem. Rev. 2020, 120,1788.
[1]	(a) Govindasamy, M.; Wolf, W. M.; Helmut, S. Chem. Rev. 2001, 101,2125.
	(b) Cristina, W. N.; Gilson, Z.; Joao, B. T. R. Chem. Rev. 2004, 104, 6255.
	(c) Pang, Y. Q.; An, B. J.; Lou, L. L.; Zhang, J. S.; Yan, J.; Huang, L.; Li, X. S.; Yin, S. J. Med. Chem. 2017, 60,7300.
[2]	(a) Corinne, M.; Philippe, D. Org. Lett. 2000, 2,1705.
	(b) Li, Y. M.; Wang, H. F.; Li, X. Y.; Chen, T.; Zhao, D. F. Tetrahedron 2010, 66,8583.
[3]	(a) Nobukazu, T. J. Org. Chem. 2007, 72,1241.
[8]	(c) Wang, Y. L.; Zhang, L. B.; Niu, J. L.; Song, M. P. Chin. J. Org. Chem. 2019, 39,1761(in Chinese).
	(王云龙, 张林宝, 牛俊龙, 宋毛平, 有机化学, 2019, 39,1761.)
	(d) Zhang, M. F.; Li, R. P.; Yang, Z.; Feng, R. K. Chin. J. Org. Chem. 2020, 40,714(in Chinese).
	(张梦帆, 李瑞鹏, 杨震, 冯若昆, 有机化学, 2020, 40,714.)
[9]	(a) Matthieu, C.; Floryan, D. C. Angew. Chem., Int. Ed. 2013, 52,9896.
	(b) Liu, J. D.; Yu, L.; Zhuang, S. B.; Gui, Q. W.; Chen, X.; Wang, W. D.; Tan, Z. Chem. Commun. 2015, 51,6418.
[10]	Masayuki, I.; Yuta, T.; Kiyohiko, N.; Yasushi, N. Org. Lett. 2014, 16,4920.
[11]	Anup, M.; Harekrishna, S.; Mahiuddin, B. Org. Lett. 2016, 18,3202.
[12]	Bijaya, K. S.; Gurupada, B.; Ranjan, J. ChemistrySelect 2017, 2,9227.
[13]	(a) Xie, T. H.; Jiang, X. Y.; Mi, Z. S.; Li, X.; Xu, X. H.; Bai, R. R.; Shuai, Q.; Xie, Y. Y. Chin. J. Org. Chem. 2019, 39,3294(in Chinese).
	(谢庭辉, 蒋筱莹, 米治胜, 李雪, 徐小河, 白仁仁, 帅棋, 谢媛媛, 有机化学, 2019, 39,3294.)
	(b) Abdukader, A.; Wang, R.; Mamat, M.; Liu, C. J. Chin. J. Org. Chem. 2020, 40,1697(in Chinese).
	( 阿布力米提•阿布都卡德尔, 汪荣, 买尔哈巴•买买提, 刘晨江, 有机化学, 2020, 40,1697.)
	(c) Liu, K. J.; Wang, Z.; Lu, L. H.; Chen, J. Y.; Zeng, F.; Lin, Y. W.; Cao, Z.; Yu, X. Y.; He, W. M. Green Chem. 2021, 23,496.
	(d) Cao, Z.; Zhu, Q.; Lin, Y. Wu.; He, W. M. Chin. Chem. Lett. 2019, 30,2132.
[14]	Liene, G.; Olafs, D. Angew. Chem., Int. Ed. 2014, 53,10209.
[15]	Ma, X. L.; Wang, Q.; Feng, X. Y.; Mo, Z. Y.; Pan, Y, M.; Chen, Y. Y.; Xin, M.; Xu, Y. L. Green Chem. 2019, 21,3547.

Entry	Catalyst	Base	Temp./℃	Yield/%
1	Ni(acac)₂	NaOAc	60	0
2	Co(acac)₂	NaOAc	60	0
3	Pd(OAc)₂	NaOAc	60	0
4	Cu(OAc)₂	NaOAc	60	67
5	Cu(CHCN)₄PF₆	NaOAc	60	66
6^c	Cu(OAc)₂	NaOAc	60	48
7^d	Cu(OAc)₂	NaOAc	60	0
8^e	Cu(OAc)₂	NaOAc	60	70
9	Cu(OAc)₂	NaOAc	25	Trace
10	Cu(OAc)₂	NaOAc	40	30
11	Cu(OAc)₂	NaOAc	80	77
12	Cu(OAc)₂	CsOAc	80	65
13	Cu(OAc)₂	NaOPiv	80	67
14	Cu(OAc)₂	NaH₂PO₄	80	0
15	Cu(OAc)₂	Na₂HPO₄	80	Trace
16	Cu(OAc)₂	Na₃PO₄	80	35
17	Cu(OAc)₂	t-BuONa	80	0
18	Cu(OAc)₂	Cs₂CO₃	80	0
19^f	Cu(OAc)₂	NaOAc	80	54

Entry	Catalyst	Base	Temp./℃	Yield/%
1	Ni(acac)₂	NaOAc	60	0
2	Co(acac)₂	NaOAc	60	0
3	Pd(OAc)₂	NaOAc	60	0
4	Cu(OAc)₂	NaOAc	60	67
5	Cu(CHCN)₄PF₆	NaOAc	60	66
6^c	Cu(OAc)₂	NaOAc	60	48
7^d	Cu(OAc)₂	NaOAc	60	0
8^e	Cu(OAc)₂	NaOAc	60	70
9	Cu(OAc)₂	NaOAc	25	Trace
10	Cu(OAc)₂	NaOAc	40	30
11	Cu(OAc)₂	NaOAc	80	77
12	Cu(OAc)₂	CsOAc	80	65
13	Cu(OAc)₂	NaOPiv	80	67
14	Cu(OAc)₂	NaH₂PO₄	80	0
15	Cu(OAc)₂	Na₂HPO₄	80	Trace
16	Cu(OAc)₂	Na₃PO₄	80	35
17	Cu(OAc)₂	t-BuONa	80	0
18	Cu(OAc)₂	Cs₂CO₃	80	0
19^f	Cu(OAc)₂	NaOAc	80	54

空气氧化的铜催化苯甲酸衍生物邻位C(sp²)—H键的硒化反应

Copper-Catalyzed Vicinal C(sp²)—H Selenylation of Benzoic Acid Derivatives Using Air as Oxidant

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空气氧化的铜催化苯甲酸衍生物邻位C(sp2)—H键的硒化反应