Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines
-
* Corresponding authors.
E-mail addresses: oulijuanann@163.com (L.-J. Ou), weiminhe@usc.edu.cn (W.-M. He).
Citation:
Wen-Tao Ouyang, Jun Jiang, Yan-Fang Jiang, Ting Li, Yuan-Yuan Liu, Hong-Tao Ji, Li-Juan Ou, Wei-Min He. Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines[J]. Chinese Chemical Letters,
;2024, 35(10): 110038.
doi:
10.1016/j.cclet.2024.110038
J.P. Barham, B. König, Angew. Chem. Int. Ed. 59 (2020) 11732–11747.
doi: 10.1002/anie.201913767
X.Y. Yu, J.R. Chen, W.J. Xiao, Chem. Rev. 121 (2021) 506–561.
doi: 10.1021/acs.chemrev.0c00030
H. Wang, Y.M. Tian, B. König, Nat. Rev. Chem. 6 (2022) 745–755.
doi: 10.1038/s41570-022-00421-6
N. Holmberg-Douglas, D.A. Nicewicz, Chem. Rev. 122 (2022) 1925–2016.
doi: 10.1021/acs.chemrev.1c00311
Y. Lv, H. Ding, J. You, W. Wei, D. Yi, Chin. Chem. Lett. 35 (2024) 109107.
doi: 10.1016/j.cclet.2023.109107
S. Saranya, S. Radhika, C.M. Afsina Abdulla, G. Anilkumar, J. Heterocycl. Chem. 58 (2021) 1570–1580.
doi: 10.1002/jhet.4261
I.V. Machado, J.R.N. dos Santos, M.A.P. Januario, A.G. Corrêa, Ultrason. Sonochem. 78 (2021) 105704.
doi: 10.1016/j.ultsonch.2021.105704
K.S. Wahan, G. Bhargava, A.P. Chawla, Curr. Org. Chem. 27 (2023) 1010–1019.
doi: 10.2174/1385272827666230911130127
T. Xiong, H. Yuan, F. Yang, J. Jiang, Green Synth. Catal. 3 (2022) 46–52.
doi: 10.1016/j.gresc.2021.10.005
C.G. Joseph, G. Li Puma, A. Bono, D. Krishnaiah, Ultrason. Sonochem. 16 (2009) 583–589.
doi: 10.1016/j.ultsonch.2009.02.002
D. Paustian, M. Franke, M. Stelter, P. Braeutigam, Catalysts 12 (2022) 754.
doi: 10.3390/catal12070754
A.A. Isari, F. Hayati, B. Kakavandi, et al., Chem. Eng. J. 392 (2020) 123685.
doi: 10.1016/j.cej.2019.123685
A. Mukherjee, S. Das, Y.H. Ahn, J. Water Process Eng. 49 (2022) 103186.
doi: 10.1016/j.jwpe.2022.103186
M. Montana, V. Montero, O. Khoumeri, P. Vanelle, Molecules 25 (2020) 2784.
doi: 10.3390/molecules25122784
X. Jiang, K. Wu, R. Bai, P. Zhang, Y. Zhang, Eur. J. Med. Chem. 229 (2022) 114085.
doi: 10.1016/j.ejmech.2021.114085
P. Rani Kiran, S. Chahal, et al., New J. Chem. 45 (2021) 18722–18763.
doi: 10.1039/D1NJ03445F
K.L. Wang, H.T. Ji, L.J. Ou, W.M. He, Eur. J. Org. Chem. 26 (2023) e202300752.
Z. Wang, N. Meng, Y. Lv, et al., Chin. Chem. Lett. 34 (2023) 107599.
doi: 10.1016/j.cclet.2022.06.022
N. Meng, Y. Lv, Q. Liu, et al., Chin. Chem. Lett. 32 (2021) 258–262.
doi: 10.1016/j.cclet.2020.11.034
J. Sun, H. Yang, B. Zhang, Green Chem. 24 (2022) 858–863.
doi: 10.1039/D1GC03992J
M. Wang, J. Liu, Y. Zhang, P. Sun, Adv. Synth. Catal. 364 (2022) 2660–2665.
doi: 10.1002/adsc.202200455
H. Zhang, J. Xu, Y. Ouyang, et al., Chin. Chem. Lett. 33 (2022) 2036–2040.
doi: 10.1016/j.cclet.2021.09.069
L. Ding, K. Niu, Y. Liu, Q. Wang, Chin. Chem. Lett. 33 (2022) 4057–4060.
doi: 10.1016/j.cclet.2021.12.053
Y. Deng, X. Cheng, H. Tan, et al., Adv. Synth. Catal. 365 (2023) 865–870.
doi: 10.1002/adsc.202300035
X. Shi, Y. Cao, Y. Liu, et al., Org. Chem. Front. 10 (2023) 1296–1300.
doi: 10.1039/D2QO02019J
J. Zhu, Y. Guo, Y. Zhang, et al., Green Chem. 25 (2023) 986–992.
doi: 10.1039/D2GC04521D
F. Cheng, L. Fan, Q. Lv, X. Chen, B. Yu, Green Chem. 25 (2023) 7971–7977.
doi: 10.1039/D3GC02545D
J. Ren, C. Pi, X. Cui, Y. Wu, Green Chem. 24 (2022) 3017–3022.
doi: 10.1039/D1GC04825B
J.C. Hou, J. Jiang, Y.C. Wen, et al., J. Org. Chem. 89 (2024) 6117–6125.
doi: 10.1021/acs.joc.4c00087
H.Y. Song, J. Jiang, C. Wu, et al., Green Chem. 25 (2023) 3292–3296.
doi: 10.1039/D2GC04843D
H. Hou, C. Wang, X. Cheng, et al., Catal. Sci. Technol. 13 (2023) 305–309.
doi: 10.1039/D2CY01640K
J. Xu, L. Huang, L. He, et al., Green Chem. 23 (2021) 6632–6638.
doi: 10.1039/D1GC01899J
L. Dai, G. Zhong, Chin. J. Org. Chem. 43 (2023) 2589–2590.
doi: 10.6023/cjoc202300042
J. Lu, X.K. He, X. Cheng, et al., Adv. Synth. Catal. 362 (2020) 2178–2182.
doi: 10.1002/adsc.202000116
L.Y. Xie, S. Peng, L.H. Yang, et al., Green Chem. 23 (2021) 374–378.
doi: 10.1039/D0GC02844D
K.C.C. Aganda, B. Hong, A. Lee, Adv. Synth. Catal. 363 (2021) 1443–1448.
doi: 10.1002/adsc.202001396
Y. He, G. Wang, W. Hu, et al., ACS Sustain. Chem. Eng. 11 (2023) 910–920.
doi: 10.1021/acssuschemeng.2c04720
J.W. Yuan, J.L. Zhu, H.L. Zhu, et al., Org. Chem. Front. 7 (2020) 273–285.
doi: 10.1039/C9QO01322A
J. Li, J. Hu, Y. Xiao, et al., Tetrahedron Lett. 88 (2022) 153511.
doi: 10.1016/j.tetlet.2021.153511
Y. Li, M. Gao, L. Wang, X. Cui, Org. Biomol. Chem. 14 (2016) 8428–8432.
doi: 10.1039/C6OB01283C
A. Gupta, M.S. Deshmukh, N. Jain, J. Org. Chem. 82 (2017) 4784–4792.
doi: 10.1021/acs.joc.7b00464
W. Wei, L. Wang, P. Bao, et al., Org. Lett. 20 (2018) 7125–7130.
doi: 10.1021/acs.orglett.8b03079
L. Zheng, Y.E. Qian, Y.Z. Hu, et al., Org. Lett. 23 (2021) 1643–1647.
doi: 10.1021/acs.orglett.1c00064
Q. Yang, Z. Yang, Y. Tan, et al., Adv. Synth. Catal. 361 (2019) 1662–1667.
doi: 10.1002/adsc.201801661
Y. Tan, B. Liu, Y.P. Han, et al., Chem. Asian J. 15 (2020) 3365–3369.
doi: 10.1002/asia.202000916
Y.F. Si, X.L. Chen, X.Y. Fu, et al., ACS Sustain. Chem. Eng. 8 (2020) 10740–10746.
Y. Li, C. Dai, S. Xie, P. Liu, P. Sun, Org. Lett. 23 (2021) 5906–5910.
doi: 10.1021/acs.orglett.1c02014
W.T. Ouyang, H.T. Ji, J. Jiang, et al., Chem. Commun. 59 (2023) 14029–14032.
doi: 10.1039/D3CC04020H
Y.H. Lu, Z.T. Zhang, H.Y. Wu, et al., Chin. Chem. Lett. 34 (2023) 108036.
doi: 10.1016/j.cclet.2022.108036
J.F. Cui, W.Q. Zhong, J.M. Huang, J. Org. Chem. 88 (2023) 1147–1154.
doi: 10.1021/acs.joc.2c02654
Y.H. Lu, S.Y. Mu, J. Jiang, et al., ChemSusChem 16 (2023) e202300523.
doi: 10.1002/cssc.202300523
J. Zhou, Z. Li, Z. Sun, et al., J. Org. Chem. 85 (2020) 4365–4372.
doi: 10.1021/acs.joc.0c00050
L. Zhang, J. He, P. Zhang, et al., Green Synth. Catal. 4 (2023) 226–230.
doi: 10.1016/j.gresc.2022.04.004
Y. Li, X. Liang, K. Niu, et al., Org. Lett. 24 (2022) 5918–5923.
doi: 10.1021/acs.orglett.2c02150
J. Liu, Z. Huang, C. Wang, et al., Eur. J. Org. Chem. 26 (2023) e202300129.
doi: 10.1002/ejoc.202300129
H. Li, P. Chen, Z. Wu, et al., Chin. J. Org. Chem. 42 (2022) 3398–3404.
doi: 10.6023/cjoc202207009
S. Mu, H. Li, Z. Wu, et al., Chin. J. Org. Chem. 42 (2022) 4292–4299.
doi: 10.6023/cjoc202211002
Q.X. Luo, H.T. Ji, Y.H. Lu, et al., J. Org. Chem. 88 (2023) 16790–16796.
doi: 10.1021/acs.joc.3c01271
H.Y. Song, J. Jiang, Y.H. Song, et al., Chin. Chem. Lett. 35 (2024) 109246.
doi: 10.1016/j.cclet.2023.109246
H.Y. Song, F. Xiao, J. Jiang, et al., Chin. Chem. Lett. 34 (2023) 108509.
doi: 10.1016/j.cclet.2023.108509
K. Wang, J. Huang, W. Liu, et al., Chin. J. Org. Chem. 42 (2022) 2527–2534.
doi: 10.6023/cjoc202203055
R. Yi, W. He, Chin. J. Org. Chem. 43 (2023) 2985–2987.
doi: 10.6023/cjoc202300047
T. Liu, F. Xue, Z. Chen, et al., J. Catal. 414 (2022) 76–83.
doi: 10.1016/j.jcat.2022.08.029
Q.H. Teng, Y. Yao, W.X. Wei, et al., Green Chem. 21 (2019) 6241–6245.
doi: 10.1039/C9GC03045J
J. Xu, H. Zhang, J. Zhao, et al., Org. Chem. Front. 7 (2020) 4031–4042.
doi: 10.1039/D0QO00872A
L. Xuan, R. Du, P. Lei, et al., Green Chem. 24 (2022) 9475–9481.
doi: 10.1039/D2GC02874C
Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112
Boqiang Wang , Yongzhuo Xu , Jiajia Wang , Muyang Yang , Guo-Jun Deng , Wen Shao . Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines. Chinese Chemical Letters, 2024, 35(9): 109502-. doi: 10.1016/j.cclet.2024.109502
Chong-Yang Shi , Jian-Xing Gong , Zhen Li , Chao Shu , Long-Wu Ye , Qing Sun , Bo Zhou , Xin-Qi Zhu . Gold-catalyzed intermolecular amination of allyl azides with ynamides: Efficient construction of 3-azabicyclo[3.1.0] scaffold. Chinese Chemical Letters, 2025, 36(2): 109895-. doi: 10.1016/j.cclet.2024.109895
Wen-Jing Li , Jun-Bo Wang , Yu-Heng Liu , Mo Zhang , Zhan-Hui Zhang . Molybdenum-doped carbon nitride as an efficient heterogeneous catalyst for direct amination of nitroarenes with arylboronic acids. Chinese Chemical Letters, 2025, 36(3): 110001-. doi: 10.1016/j.cclet.2024.110001
Xin Li , Jia-Min Lu , Bo Li , Chen Zhao , Bei-Bei Yang , Li Li . Chiroptical sensing for remote chiral amines via a C–H activation reaction. Chinese Chemical Letters, 2025, 36(5): 110310-. doi: 10.1016/j.cclet.2024.110310
Pengcheng Su , Shizheng Chen , Zhihong Yang , Ningning Zhong , Chenzi Jiang , Wanbin Li . Vapor-phase postsynthetic amination of hypercrosslinked polymers for efficient iodine capture. Chinese Chemical Letters, 2024, 35(9): 109357-. doi: 10.1016/j.cclet.2023.109357
Yu Xiong , Li-Jun Hu , Jian-Guo Song , Di Zhang , Yi-Shuang Peng , Xiao-Jun Huang , Jian Hong , Bin Zhu , Wen-Cai Ye , Ying Wang . Structure elucidation of plumerubradins A–C: Correlations between 1H NMR signal patterns and structural information of [2+2]-type cyclobutane derivatives. Chinese Chemical Letters, 2025, 36(5): 110149-. doi: 10.1016/j.cclet.2024.110149
Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF3·OEt2-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
Yuan Zhang , Shenghao Gong , A.R. Mahammed Shaheer , Rong Cao , Tianfu Liu . Plasmon-enhanced photocatalytic oxidative coupling of amines in the air using a delicate Ag nanowire@NH2-UiO-66 core-shell nanostructures. Chinese Chemical Letters, 2024, 35(4): 108587-. doi: 10.1016/j.cclet.2023.108587
Jun Zhang , Zhiyao Zheng , Can Zhu . Stereochemical editing: Catalytic racemization of secondary alcohols and amines. Chinese Chemical Letters, 2024, 35(5): 109160-. doi: 10.1016/j.cclet.2023.109160
Ling-Hao Zhao , Hai-Wei Yan , Jian-Shuang Jiang , Xu Zhang , Xiang Yuan , Ya-Nan Yang , Pei-Cheng Zhang . Effective assignment of positional isomers in dimeric shikonin and its analogs by 1H NMR spectroscopy. Chinese Chemical Letters, 2024, 35(5): 108863-. doi: 10.1016/j.cclet.2023.108863
Bicheng Zhu , Jingsan Xu . S-scheme heterojunction photocatalyst for H2 evolution coupled with organic oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100327-100327. doi: 10.1016/j.cjsc.2024.100327
Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
Ruike Hu , Kangmin Wang , Junxiang Liu , Jingxian Zhang , Guoliang Yang , Liqiu Wan , Bijin Li . Extended π-conjugated systems by external ligand-assisted C−H olefination of heterocycles: Facile access to single-molecular white-light-emitting and NIR fluorescence materials. Chinese Chemical Letters, 2025, 36(4): 110113-. doi: 10.1016/j.cclet.2024.110113
Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C3N4/AgI.x.y heterojunction photocatalyst for simultaneous and stoichiometric production of H2 and H2O2 from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
Huaixiang Yang , Miao-Miao Li , Aijun Zhang , Jiefei Guo , Yongqi Yu , Wei Ding . Visible-light-induced photocatalyst- and metal-free radical phosphinoyloximation of alkenes with tert-butyl nitrite as bifunctional reagent. Chinese Chemical Letters, 2025, 36(3): 110425-. doi: 10.1016/j.cclet.2024.110425
Yuan Teng , Zichun Zhou , Jinghua Chen , Siying Huang , Hongyan Chen , Daibin Kuang . Dual atom-bridge effect promoting interfacial charge transfer in 2D/2D Cs3Bi2Br9/BiOBr epitaxial heterojunction for efficient photocatalysis. Chinese Chemical Letters, 2025, 36(2): 110430-. doi: 10.1016/j.cclet.2024.110430