光氧化还原催化串联自由基加成反应构建1,4-二酮官能团化喹喔啉-2(1H)-酮衍生物

doi:10.6023/cjoc202201025

有机化学 ›› 2022, Vol. 42 ›› Issue (5): 1396-1406.DOI: 10.6023/cjoc202201025 上一篇下一篇

研究论文

光氧化还原催化串联自由基加成反应构建1,4-二酮官能团化喹喔啉-2(1H)-酮衍生物

孙鑫^a, 屈超凡^a, 马超蕊^a, 赵筱薇^a^,^b, 柴国璧^c^,^*(), 江智勇^a^,^b^,^*()

a 河南大学河南省手性化学国际联合基地开封 475004
b 河南师范大学化学化工学院新乡 453007
c 中国烟草总公司郑州烟草研究院烟草香料基础研究重点实验室郑州 450001

收稿日期:2022-01-17 修回日期:2022-01-26 发布日期:2022-01-28
通讯作者: 柴国璧, 江智勇
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(21925103); 中国科协青年人才托举工程(2017QNRC001)

Photoredox Catalytic Cascade Radical Addition to Construct 1,4- Diketone-Functionalized Quinoxalin-2(1H)-one Derivatives

Xin Sun^a, Chaofan Qu^a, Chaorui Ma^a, Xiaowei Zhao^a^,^b, Guobi Chai^c(), Zhiyong Jiang^a^,^b()

a International Scientific and Technological Cooperation Base of Chiral Chemistry, Henan University, Kaifeng, Henan 475004
b School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
c Key Laboratory of Tobacco Flavor Basic Research of China National Tobacco Corporation, Zhengzhou Tobacco Research Institute of China National Tobacco Corporation, Zhengzhou 450001

Received:2022-01-17 Revised:2022-01-26 Published:2022-01-28
Contact: Guobi Chai, Zhiyong Jiang
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21925103); Young Elite Scientists Sponsorship Program by China Association for Science and Technology(2017QNRC001)

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摘要/Abstract

喹喔啉-2(1H)-酮的生物学重要性激发了开发高效简便合成方法学的持续追求. 其中, 对其C3—H官能团化已成为近年的研究热点, 尤其是利用光催化平台. 目前除了光催化产生的自由基直接加成喹喔啉-2(1H)-酮, 已有零星三组分串联反应策略被报道, 这一手段是基于烯烃优先接受自由基加成, 由所产生的自由基物种随后加成到喹喔啉-2(1H)-酮. 鉴于多组分反应能够有效丰富该化合物类型, 发展新的策略成为必然. 报道了α-溴代芳基乙酮与喹喔啉-2(1H)-酮的光氧化还原催化反应, 用于构建重要的1,4-二酮官能团化衍生物. 这是一个新的串联反应策略: 自由基首先加成到喹喔啉-2(1H)-酮, 所产生的中间体进一步接受溴代物产生的自由基加成或与溴代物发生S_N2反应.

关键词: 可见光, 光氧化还原催化, 自由基加成, 串联反应, 2-羟基喹喔啉

The biological importance of quinoxalin-2(1H)-ones has inspired increasing pursuit for the development of efficient and expedient synthetic methods to access these entities. Among them, C3—H functionalization of quinoxalin-2(1H)- ones has been a sought-after strategy in recent years, especially using photocatalysis platform to trigger radical intermediates. Besides the direct addition of photocatalysis-yielding radicals to 3-position of quinoxalin-2(1H)-ones, a handful of three- component cascade reactions have been described, wherein olefins were used to preferentially accept radicals to generate new radical intermediates to experience the second addition process. Given the robust ability of cascade strategy to enrich the varieties of quinoxalin-2(1H)-ones, the exploration of new protocols remains a highly attractive task. Herein, we report photoredox catalytic reactions of quinoxalin-2(1H)-ones with 2-bromo-1-arylethan-1-ones as the partners, leading to a series of valuable 1,4-diketone-functionalized quinoxalin-2(1H)-one derivatives with satisfactory results. This is an unprecedented cascade reaction strategy, involving radical addition to quinoxalin-2(1H)-ones and the resultant intermediates to accept a second addition of radicals generated from bromide substrates or to experience S_N2 reaction with bromides.

Key words: visible light, photoredox catalysis, radical addition, cascade reaction, quinoxalin-2(1H)-ones

引用此文

孙鑫, 屈超凡, 马超蕊, 赵筱薇, 柴国璧, 江智勇. 光氧化还原催化串联自由基加成反应构建1,4-二酮官能团化喹喔啉-2(1H)-酮衍生物[J]. 有机化学, 2022, 42(5): 1396-1406.

Xin Sun, Chaofan Qu, Chaorui Ma, Xiaowei Zhao, Guobi Chai, Zhiyong Jiang. Photoredox Catalytic Cascade Radical Addition to Construct 1,4- Diketone-Functionalized Quinoxalin-2(1H)-one Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1396-1406.

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[1]	(a) Shi, L.-L.; Zhou, H.; Wu, J.-F.; Li, X. Mini-Rev. Org. Chem. 2015, 12, 96. doi: 10.2174/1570193X11666141029004418 pmid: 17100630
	(b) Carta, A.; Piras, S.; Loriga, G.; Paglietti, G. Mini-Rev. Med. Chem. 2006, 6, 1179. pmid: 17100630
	(c) Li, X.; Yang, K.; Li, W.; Xu, W. Drugs Future 2006, 31, 979. doi: 10.1358/dof.2006.031.11.1037128 pmid: 17100630
	(d) Akins, P. T.; Atkinson, R. P. Curr. Med. Res. Opin. 2002, 18, 9. pmid: 17100630
[2]	For selected reviews, see: (a) Ke, Q.; Yan, G.; Yu, J.; Wu, X. Org. Biomol. Chem. 2019, 17, 5863. doi: 10.1039/C9OB00782B
	(b) Monika, M.; Selvakumar, S. Synthesis 2019, 4113.
	(c) Ghosh, P.; Das, S. Synth. Commun. 2020, 50, 2266. doi: 10.1080/00397911.2020.1765257
	(d) Meng, W.; Xu, K.; Guo, B.; Zeng, C. Chin. J. Org. Chem. 2021, 41, 2621. (in Chinese) doi: 10.6023/cjoc202102001
	(孟薇, 徐坤, 郭兵冰, 曾程初, 有机化学, 2021, 41, 2621.) doi: 10.6023/cjoc202102001
	(e) Liu, X.; Li, W.; Zhuang, C.; Cao, H. Chin. J. Org. Chem. 2021, 41, 3459. (in Chinese) doi: 10.6023/cjoc202103032
	(刘想, 李文, 庄灿展, 曹华, 有机化学, 2021, 41, 3459.) doi: 10.6023/cjoc202103032
	(f) Li, D.; Wang, X.; Li, S.; Fu, C.; Li, Q.; Xu, D.; Ma, Y. Chin. J. Org. Chem. 2021, 41, 4610. (in Chinese) doi: 10.6023/cjoc202107042
	(李丹丹, 王晓辰, 李闪闪, 付晨雨, 李倩倩, 许东涛, 马莹莹, 有机化学, 2021, 41, 4610.) doi: 10.6023/cjoc202107042
[3]	For selected recent examples of direct functionalization except of photocatalytic reactions, see: (a) Liu, S.; Huang, Y.; Qing, F.-L.; Xu, X.-H. Org. Lett. 2018, 20, 5497. doi: 10.1021/acs.orglett.8b02451 pmid: 32392413
	(b) Dutta, H. S.; Ahmad, A.; Khan, A. A.; Kumar, M.; Raziullah; Koley, D. Adv. Synth. Catal. 2019, 361, 5534. doi: 10.1002/adsc.201901212 pmid: 32392413
	(c) Zheng, D.; Studer, A. Org. Lett. 2019, 21, 325. doi: 10.1021/acs.orglett.8b03849 pmid: 32392413
	(d) Shen, J.; Xu, J.; Huang, L.; Zhu, Q.; Zhang, P. Adv. Synth. Catal. 2020, 362, 230. doi: 10.1002/adsc.201901314 pmid: 32392413
	(e) Lu, J.; He, X.-K.; Cheng, X.; Zhang, A.-J.; Xu, G.-Y.; Xuan, J. Adv. Synth. Catal. 2020, 362, 2178. doi: 10.1002/adsc.202000116 pmid: 32392413
	(f) Su, H.-Y.; Zhu, X.-L.; Huang, Y.; Xu, X.-H.; Qing, F.-L. Chem. Commun. 2020, 56, 12805. doi: 10.1039/D0CC05623E pmid: 32392413
	(g) Wang, J.; Sun, B.; Zhang, L.; Xu, T.; Xie, Y.; Jin, C. Org. Chem. Front. 2020, 7, 113. doi: 10.1039/C9QO01055F pmid: 32392413
	(h) Yuan, J.-W.; Zhu, J.-L.; Zhu, H.-L.; Peng, F.; Yang, L.-Y.; Mao, P.; Zhang, S.-R.; Li, Y.-C.; Qu, L.-B. Org. Chem. Front. 2020, 7, 273. doi: 10.1039/C9QO01322A pmid: 32392413
	(i) Xu, J.; Zhang, H.; Zhao, J.; Ni, Z.; Zhang, P.; Shi, B.-F.; Li, W. Org. Chem. Front. 2020, 7, 4031. doi: 10.1039/D0QO00872A pmid: 32392413
	(j) Meng, N.; Wang, L.; Liu, Q.; Li, Q.; Lv, Y.; Yue, H.; Wang, X.; Wei, W. J. Org. Chem. 2020, 85, 6888. doi: 10.1021/acs.joc.9b03505 pmid: 32392413
	(k) Xu, J.; Yang, H.; He, L.; Huang, L.; Shen, J.; Li, W.; Zhang, P. Org. Lett. 2021, 23, 195. doi: 10.1021/acs.orglett.0c03918 pmid: 32392413
	(l) Wen, J.; Yang, X.; Yan, K.; Qin, H.; Ma, J.; Sun, X.; Yang, J.; Wang, H. Org. Lett. 2021, 23, 1081. doi: 10.1021/acs.orglett.0c04296 pmid: 32392413
	(m) He, X.-K.; Lu, J.; Zhang, A.-J.; Zhang, Q.-Q.; Xu, G.-Y.; Xuan, J. Org. Lett. 2020, 22, 5984. doi: 10.1021/acs.orglett.0c02080 pmid: 32392413
	(n) Niu, K.; Song, L.; Hao, Y.; Liu, Y.; Wang, Q. Chem. Commun. 2020, 56, 11673. doi: 10.1039/D0CC05391K pmid: 32392413
	(o) Clinton, C. D.; Prasad, C. D.; Thombal, R. S.; Lee, Y. R. Adv. Synth. Catal. 2021, 363, 776. doi: 10.1002/adsc.202001182 pmid: 32392413
[4]	For a review on photocatalytic functionalization, see: (a) Rostoll-Berenguer, J.; Blay, G.; Pedro, J. R.; Vila, C. Eur. J. Org. Chem. 2020, 6148.
[5]	(a) Bao, P.; Liu, F.; Lv, Y.; Yue, H.; Li, J.-S.; Wei, W. Org. Chem. Front. 2020, 7, 492. doi: 10.1039/C9QO01334B
	(b) Dai, C.; Zhan, Y.; Liu, P.; Sun, P. Green Chem. 2021, 23, 314. doi: 10.1039/D0GC03697H
	(c) Aganda, K. C. C.; Hong, B.; Lee, A. Adv. Synth. Catal. 2021, 363, 1443. doi: 10.1002/adsc.202001396
[6]	(a) Meng, N.; Lv, Y.; Liu, Q.; Liu, R.; Zhao, X.; Wei, W. Chin. Chem. Lett. 2021, 32, 258. doi: 10.1016/j.cclet.2020.11.034
	(b) Yang, X.; Meng, W.-D.; Xu, X.-H.; Huang, Y. Org. Chem. Front. 2021, 8, 6597. doi: 10.1039/D1QO01170G
[7]	For selected reviews, see: (a) Lv, X.; Xu, H.; Yin, Y.; Zhao, X.; Jiang, Z. Chin. J. Chem. 2020, 38, 1480. doi: 10.1002/cjoc.202000306
	(b) Yin, Y.; Zhao, X.; Qiao, B.; Jiang, Z. Org. Chem. Front. 2020, 7, 1283. doi: 10.1039/D0QO00276C
	(c) Yin, Y.; Zhao, X.; Jiang, Z. ChemCatChem 2020, 12, 4471. doi: 10.1002/cctc.202000741
	For selected examples see: (d) Shao, T.; Yin, Y.; Lee, R.; Zhao, X.; Chai, G.; Jiang, Z. Adv. Synth. Catal. 2018, 360, 1754. doi: 10.1002/adsc.201800135
	(e) Li, J.; Gu, Z.; Zhao, X.; Qiao, B.; Jiang, Z. Chem. Commun. 2019, 55, 12916. doi: 10.1039/C9CC07380A
	(f) Qiao, B.; Li, C.; Zhao, X.; Yin, Y.; Jiang, Z. Chem. Commun. 2019, 55, 7534. doi: 10.1039/C9CC03661J
	(g) Yin, Y.; Dai, Y.; Jia, H.; Li, J.; Bu, L.; Qiao, B.; Zhao, X.; Jiang, Z. J. Am. Chem. Soc. 2018, 140, 6083. doi: 10.1021/jacs.8b01575
	(h) Cao, K.; Tan, S. M.; Lee, R.; Yang, S.; Jia, H.; Zhao, X.; Qiao, B.; Jiang, Z. J. Am. Chem. Soc. 2019, 141, 5437. doi: 10.1021/jacs.9b00286
	(i) Yin, Y.; Li, Y.; Gonçalves, T. P.; Zhan, Q.; Wang, G.; Zhao, X.; Qiao, B.; Huang, K.-W.; Jiang, Z. J. Am. Chem. Soc. 2020, 142, 19451. doi: 10.1021/jacs.0c08329
	(j) Kong, M.; Tan, Y.; Zhao, X.; Qiao, B.; Tan, C.-H.; Cao, S.; Jiang, Z. J. Am. Chem. Soc. 2021, 143, 4024. doi: 10.1021/jacs.1c01073
	(k) Guo, Z.; Chen, X.; Fang, H.; Zhao, X.; Jiang, Z. Sci. China Chem. 2021, 64, 1522. doi: 10.1007/s11426-021-1019-2
	(l) Hu, W.; Zhan, Q.; Zhou, H.; Cao, S.; Jiang, Z. Chem. Sci. 2021, 12, 6543. doi: 10.1039/D1SC01470F
	(m) Chen, X.; Wei, W.; Li, C.; Zhou, H.; Qiao, B.; Jiang, Z. Org. Lett. 2021, 23, 8744. doi: 10.1021/acs.orglett.1c03204
	(n) Chai, X.; Hu, X.; Zhao, X.; Yin, Y.; Cao, S.; Jiang, Z. Angew. Chem. Int. Ed. 2022, 61, e202115110.
	(o) Tan, Y.; Yin, Y.; Cao, S.; Zhao, X.; Qu, G.; Jiang, Z. Chin. J. Catal. 2022, 43, 558. doi: 10.1016/S1872-2067(21)63887-1
[8]	(a) Zhao, Y.; Zhang, C.; Chin, K. F.; Pytela, O.; Wei, G.; Liu, H.; Bureš, F.; Jiang, Z. RSC Adv. 2014, 4, 30062.
	(b) Liu, X.; Ye, X.; Bureš, F.; Liu, H.; Jiang, Z. Angew. Chem. Int. Ed. 2015, 54, 11443.
	(c) Shao, T.; Jiang, Z. Acta Chim. Sinica 2017, 75, 70. (in Chinese)
	(邵天举, 江智勇, 化学学报, 2017, 75, 70.)
	(d) Jia, H.; Qiao, B.; Jiang, Z. Acta Chim. Sinica 2021, 79, 1477. (in Chinese)
	(贾红绍, 乔保坤, 江智勇, 化学学报, 2021, 79, 1477.)
	(e) Yang, H.; Li, H.; Wei, G.; Jiang, Z. Angew. Chem. Int. Ed. 2021, 60, 19696.
[9]	Badawy, M. A.; Mohamed, G. G.; Omar, M. M.; Nassar, M. M.; Kamel, A. B. Eur. J. Chem. 2010, 4, 282.
[10]	See the Supporting Information for the details.
[11]	Li, J.; Kong, M.; Qiao, B.; Lee, R.; Zhao, X.; Jiang, Z. Nat. Commun. 2018, 9, 2445.

Entry	Base (equiv.)	Solvent (mL)	t/h	Yield^b%
1	NaHCO₃ (3.0)	CH₂Cl₂ (1.5)	24	58
2	NaHCO₃ (3.0)	CH₂Cl₂ (1.5)	36	55
3	NaHCO₃ (3.0)	THF (1.5)	24	N.R.
4	NaHCO₃ (3.0)	PhCl (1.5)	24	46
5	NaHCO₃ (3.0)	Ethyl acetate (1.5)	24	28
6	NaHCO₃ (3.0)	MeOH (1.5)	24	27
7	NaHCO₃ (3.0)	CH₂Cl₂ (3.0)	24	48
8^c	NaHCO₃ (3.0)	CH₂Cl₂ (1.5)	24	45
9	KHCO₃ (3.0)	CH₂Cl₂ (1.5)	24	42
10	Na₂CO₃ (3.0)	CH₂Cl₂ (1.5)	24	44
11	Diphenylphosphate (1.0)	CH₂Cl₂ (1.5)	24	<5
12	NaHCO₃ (1.0)	CH₂Cl₂ (1.5)	24	24
13	NaHCO₃ (2.0)	CH₂Cl₂ (1.5)	24	45
14	NaHCO₃ (5.0)	CH₂Cl₂ (1.5)	24	61

Entry	Base (equiv.)	Solvent (mL)	t/h	Yield^b%
1	NaHCO₃ (3.0)	CH₂Cl₂ (1.5)	24	58
2	NaHCO₃ (3.0)	CH₂Cl₂ (1.5)	36	55
3	NaHCO₃ (3.0)	THF (1.5)	24	N.R.
4	NaHCO₃ (3.0)	PhCl (1.5)	24	46
5	NaHCO₃ (3.0)	Ethyl acetate (1.5)	24	28
6	NaHCO₃ (3.0)	MeOH (1.5)	24	27
7	NaHCO₃ (3.0)	CH₂Cl₂ (3.0)	24	48
8^c	NaHCO₃ (3.0)	CH₂Cl₂ (1.5)	24	45
9	KHCO₃ (3.0)	CH₂Cl₂ (1.5)	24	42
10	Na₂CO₃ (3.0)	CH₂Cl₂ (1.5)	24	44
11	Diphenylphosphate (1.0)	CH₂Cl₂ (1.5)	24	<5
12	NaHCO₃ (1.0)	CH₂Cl₂ (1.5)	24	24
13	NaHCO₃ (2.0)	CH₂Cl₂ (1.5)	24	45
14	NaHCO₃ (5.0)	CH₂Cl₂ (1.5)	24	61

Entry	Variation from the standard conditions	Yield^b%
1	No NaHCO₃	<10
2	No DPZ	<5
3	No light	N.R.
4	Under air	N.R.

Entry	Variation from the standard conditions	Yield^b%
1	No NaHCO₃	<10
2	No DPZ	<5
3	No light	N.R.
4	Under air	N.R.

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[2]	朱彦硕, 王红言, 舒朋华, 张克娜, 王琪琳. 烷氧自由基引发1,5-氢原子转移实现C(sp³)—H键官能团化的研究进展[J]. 有机化学, 2024, 44(1): 1-17.
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[11]	刘静, 郝健, 沈其龙. 可见光促进的含色氨酸寡肽与YlideFluor试剂的直接三氟甲基化反应研究[J]. 有机化学, 2023, 43(4): 1517-1524.
[12]	曾成富, 何媛, 李清, 董琳. Ir(III)催化新型三组分串联三氟乙氧基化反应并一锅法构建复杂酰胺化合物[J]. 有机化学, 2023, 43(3): 1115-1123.
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光氧化还原催化串联自由基加成反应构建1,4-二酮官能团化喹喔啉-2(1H)-酮衍生物

Photoredox Catalytic Cascade Radical Addition to Construct 1,4- Diketone-Functionalized Quinoxalin-2(1H)-one Derivatives

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