Citation: Liu Kai-Jian, Deng Ji-Hui, Zeng Tang-Yu, Chen Xin-Jie, Huang Ying, Cao Zhong, Lin Ying-Wu, He Wei-Min. 1, 2-Diethoxyethane catalyzed oxidative cleavage of gem-disubstituted aromatic alkenes to ketones under minimal solvent conditions[J]. Chinese Chemical Letters, ;2020, 31(7): 1868-1872. doi: 10.1016/j.cclet.2020.01.036 shu

1, 2-Diethoxyethane catalyzed oxidative cleavage of gem-disubstituted aromatic alkenes to ketones under minimal solvent conditions

a.
Department of Chemistry, Hunan University of Science and Engineering, Yongzhou 425100, China
b.
Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, Changsha University of Science and Technology, Changsha 410114, China
c.
School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China
d.
School of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, China

weiminhe2016@yeah.net

Received Date: 21 November 2019
Revised Date: 1 January 2020
Accepted Date: 17 January 2020
Available Online: 17 January 2020

Figures(7)

Aerobic oxidation using pure dioxygen gas as the oxidant has attracted much attention, but its application in synthetic chemistry has been significantly hampered by the complexity of catalytic system and potential risk of high-energy dioxygen gas. By employing 1, 2-diethoxyethane as a catalyst and ambient air as an oxidant, an efficient protocol for the construction of various aryl-alkyl and diaryl ketones through oxidative cleavage of gem-disubstituted aromatic alkenes under minimal solvent conditions has been achieved.
- Ketone,
- Oxidation,
- Ambient air,
- Oxidative cleavage
1. [1]
  (a) H. Yi, G. Zhang, H. Wang, et al., Chem. Rev. 117 (2017) 9016-9085;
  (b) M.H. Huang, W.J. Hao, G. Li, S.J. Tu, B. Jiang, Chem. Commun. (Camb.) 54 (2018) 10791-10811;
  (c) X. Gong, G. Li, Z. Gan, et al., Asian J. Org. Chem. 8 (2019) 1472-1478;
  (d) Y. Zhang, K. Sun, Q. Lv, et al., Chin. Chem. Lett. 30 (2019) 1361-1368;
  (e) H. Yue, P. Bo, B.L. Wang, et al., Chin. J. Org. Chem. 39 (2019) 463-468;
  (f) G.H. Li, D.Q. Dong, Q. Deng, S.Q. Yan, Z.L. Wang, Synthesis 51 (2019) 3313-3319;
  (g) Q. Huang, L. Zhu, D. Yi, X. Zhao, W. Wei, Chin. Chem. Lett. 31 (2020) 373-376;
  (h) K. Sun, X.L. Chen, Y.L. Zhang, et al., Chem. Commun. (Camb.) 55 (2019) 12615-12618;
  (i) L. Wang, M. Zhang, Y. Zhang, et al., Chin. Chem. Lett. 31 (2020) 67-70;
  (j) G.H. Li, D.Q. Dong, X.Y. Yu, Z.L. Wang, New J. Chem. 43 (2019) 1667-1670;
  (k) K. Sun, Y.F. Si, X.L. Chen, et al., Adv. Synth. Catal. 361 (2019) 4483-4488;
  (l) L. Wang, Y. Zhang, M. Zhang, et al., Tetrahedron Lett. 60 (2019) 1845-1848;
  (m) S. Liu, K. Chen, W.J. Hao, et al., J. Org. Chem. 84 (2019) 1964-1971;
  (n) K. Sun, B. Luan, Z. Liu, et al., Org. Biomol. Chem. 17 (2019) 4208-4211;
  (o) L. Xiong, H. Hu, C.W. Wei, B. Yu, Eur. J. Org. Chem. 2020 (2020) 1588-1597.
2. [2]
  C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev. 41 (2012) 3464-3484. doi: 10.1039/c2cs15323h
3. [3]
  (a) X. Ji, D. Li, X. Zhou, H. Huang, G.J. Deng, Green Chem. 19 (2017) 619-622;
  (b) D.F. Jiang, J.Y. Hu, W.J. Hao, et al., Org. Chem. Front. 5 (2018) 189-196;
  (c) X. Chen, Z. Wang, H. Huang, G.J. Deng, Adv. Synth. Catal. 360 (2018) 4017-4022;
  (d) F.L. Zeng, X.L. Chen, S.Q. He, et al., Org. Chem. Front. 6 (2019) 1476-1480;
  (e) Y. Xia, H. Huang, F. Zhang, G.J. Deng, Org. Lett. 21 (2019) 7489-7492;
  (f) Z. Gan, Q. Yan, G. Li, et al., Adv. Synth. Catal. 361 (2019) 4558-4567;
  (g) X. Ji, M. Tan, M. Fu, G.J. Deng, H. Huang, Org. Biomol. Chem.17 (2019) 4979-4983;
  (h) K. Chen, W.J. Hao, S.J. Tu, B. Jiang, Green Chem. 21 (2019) 675-683;
  (i) X.Zhang, S.Dong, Q.Ding, X.Fan, G.Zhang, Chin.Chem.Lett.30 (2019) 375-378;
  (j) K.J. Liu, T.Y. Zeng, J.L. Zeng, et al., Chin. Chem. Lett. 30 (2019) 2304-2308;
  (k) K.J. Liu, J.H. Deng, J. Yang, et al., Green Chem. 22 (2020) 433-438;
  (l) W.M. He, Y.W. Lin, D. Yu, Sci. China Chem. 63 (2020) 291-293.
4. [4]
  (a) J.P. Wan, Y. Gao, L. Wei, Chem. Asian J. 11 (2016) 2092-2102;
  (b) G. Urgoitia, R. SanMartin, M.T. Herrero, E. DomÃnguez, ACS Catal. 7 (2017) 3050-3060.
5. [5]
  T.J. Fisher, P.H. Dussault, Tetrahedron 73 (2017) 4233-4258. doi: 10.1016/j.tet.2017.03.039
6. [6]
  (a) K. Miyamoto, N. Tada, M. Ochiai, J. Am. Chem. Soc. 129 (2007) 2772-2773;
  (b) F.V. Singh, H.M.S. Milagre, M.N. Eberlin, H.A. Stefani, Tetrahedron Lett. 50 (2009) 2312-2316;
  (c) A. Rajagopalan, M. Lara, W. Kroutil, Adv. Synth. Catal. 355 (2013) 3321-3335;
  (d) X. Zeng, D. Xu, C. Miao, C. Xia, W. Sun, RSC Adv. 4 (2014) 46494-46497;
  (e) D.J. Lippincott, P.J. Trejo-Soto, F. Gallou, B.H. Lipshutz, Org. Lett. 20 (2018) 5094-5097.
7. [7]
  (a) M.M. Hossain, W.K. Huang, H.J. Chen, P.H. Wang, S.G. Shyu, Green Chem. 16 (2014) 3013-3017;
  (b) C. Mi, X.G. Meng, X.H. Liao, X. Peng, RSC Adv. 5 (2015) 69487-69492;
  (c) A. Gonzalez-de-Castro, J. Xiao, J. Am. Chem. Soc. 137 (2015) 8206-8218;
  (d) G. Urgoitia, R. SanMartin, M.T. Herrero, E. DomÃnguez, Adv. Synth. Catal. 358 (2016) 1150-1156;
  (e) Y. Liu, D. Xue, C. Li, J. Xiao, C. Wang, Catal. Sci. Technol. 7 (2017) 5510-5514;
  (f) C.A. Hone, A. Oâorg^TM Kearney-McMullan, R. Munday, C.O. Kappe, ChemCatChem 9 (2017) 3298-3302;
  (g) C. Zhu, D. Wei, Y. Wu, et al., J. Alloys. Compd. 778 (2019) 731-740;
  (h) B. Xiong, X. Zeng, S. Geng, et al., Green Chem. 20 (2018) 4521-4527.
8. [8]
  (a) T. Wang, N. Jiao, J. Am. Chem. Soc. 135 (2013) 11692-11695;
  (b) G.Z. Wang, X.L. Li, J.J. Dai, H.J. Xu, J. Org. Chem. 79 (2014) 7220-7225;
  (c) Y. Imada, Y. Okada, K. Noguchi, K. Chiba, Angew. Chem. Int. Ed. 58 (2019) 125-129;
  (d) Z. Cheng, W. Jin, C. Liu, Org. Chem. Front. 6 (2019) 841-845.
9. [9]
  P.M. Osterberg, J.K. Niemeier, C.J. Welch, et al., Org. Process Res. Dev. 19 (2015) 1537-1543. doi: 10.1021/op500328f
10. [10]
  (a) X. Wang, C. Wang, Y. Liu, J. Xiao, Green Chem. 18 (2016) 4605-4610;
  (b) B. Liu, F. Jin, T. Wang, X. Yuan, W. Han, Angew. Chem. Int. Ed. 56 (2017) 12712-12717;
  (c) S. Li, B. Zhu, R. Lee, B. Qiao, Z. Jiang, Org. Chem. Front. 5 (2018) 380-385;
  (d) R. Li, X. Chen, S. Wei, et al., Adv. Synth. Catal. 360 (2018) 4807-4813;
  (e) B. Liu, P. Hu, F. Xu, et al., Comm. Chem. 2 (2019) 5-12;
  (f) D.Q. Dong, L.X. Li, G.H. Li, et al., Chin. J. Catal. 40 (2019) 1494-1498;
  (g) L.Y. Xie, J.L. Hu, Y.X. Song, et al., ACS Sustainable Chem. Eng. 7 (2019) 19993-19999;
  (h) L.Y. Xie, Y.S. Lu, H.R. Ding, et al., Chinese J. Catal. 41 (2020) 1168-1173;
  (i) G. Li, Q. Yan, X. Gong, X. Dou, D. Yang, ACS Sustainable Chem. Eng. 7 (2019) 14009-14015;
  (j) L.Y. Xie, Y.L. Chen, L. Qin, et al., Org. Chem. Front. 6 (2019) 3950-3955;
  (k) Z. Wang, X. Ji, J. Zhao, H. Huang, Green Chem. 21 (2019) 5512-5516;
  (l) Y. Lv, P. Bao, H. Yue, J.S. Li, W. Wei, Green Chem. 21 (2019) 6051-6055.
11. [11]
  (a) L.H. Lu, Z. Wang, W. Xia, et al., Chin. Chem. Lett. 30 (2019) 1237-1240;
  (b) L. Peng, Z. Hu, Q. Lu, et al., Chin. Chem. Lett. 30 (2019) 2151-2156;
  (c) L. Peng, Z. Hu, Z. Tang, Y. Jiao, X. Xu, Chin. Chem. Lett. 30 (2019) 1481-1487;
  (d) W.-H. Bao, Z. Wang, X. Tang, et al., Chin. Chem. Lett. 30 (2019) 2259-2262;
  (e) Z. Cao, Q. Zhu, Y.W. Lin, W.M. He, Chin. Chem. Lett. 30 (2019) 2132-2138;
  (f) S. Peng, Y.X. Song, J.Y. He, et al., Chin. Chem. Lett. 30 (2019) 2287-2290;
  (g) Z. Wang, W.M. He, Chin. J. Org. Chem. 39 (2019) 3594-3595;
  (h) Q.W. Gui, X. He, W. Wang, et al., Green Chem. 22 (2020) 118-122;
  (j) S. Peng, Y.W. Lin, W.M. He, Chin. J. Org. Chem. 40 (2020) 541-542;
  (i) S. Peng, D. Hu, J.L. Hu, et al., Adv. Synth. Catal. 361 (2019) 5721-5726.
12. [12]
  (a) S. Mahajan, B. Sharma, K.K. Kapoor, Tetrahedron Lett. 56 (2015) 1915-1918;
  (b) O. Ravi, A. Shaikh, A. Upare, K.K. Singarapu, S.R. Bathula, J. Org. Chem. 82 (2017) 4422-4428;
  (c) G.C. Senadi, M.R. Mutra, T.Y. Lu, J.J. Wang, Green Chem. 19 (2017) 4272-4277;
  (d) R. Bashary, G.L. Khatik, Bioorg. Chem. 82 (2019) 156-162.
13. [13]
  (a) G.R. Buettner, Free Radical Biol. Med. 3(1987) 259-303;
  (b) J. Van Der Zee, D.P. Barr, R.P. Mason, Free Radical Biol. Med. 20 (1996) 199-206.
14. [14]
  (a) M.M. Hossain, S.G. Shyu, Tetrahedron 70(2014) 251-255;
  (b) K.J. Liu, S. Jiang, L.H. Lu, et al., Green Chem. 20 (2018) 3038-3043.
1. [1]
  Xiaoxue Li , Hongwei Zhou , Rongrong Qian , Xu Zhang , Lei Yu . A concise synthesis of Se/Fe materials for catalytic oxidation reactions of anthracene and polyene. Chinese Chemical Letters, 2025, 36(3): 110036-. doi: 10.1016/j.cclet.2024.110036
2. [2]
  Zhikang Wu , Guoyong Dai , Qi Li , Zheyu Wei , Shi Ru , Jianda Li , Hongli Jia , Dejin Zang , Mirjana Čolović , Yongge Wei . POV-based molecular catalysts for highly efficient esterification of alcohols with aldehydes as acylating agents. Chinese Chemical Letters, 2024, 35(8): 109061-. doi: 10.1016/j.cclet.2023.109061
3. [3]
  Chen Lian , Si-Han Zhao , Hai-Lou Li , Xinhua Cao . A giant Ce-containing poly(tungstobismuthate): Synthesis, structure and catalytic performance for the decontamination of a sulfur mustard simulant. Chinese Chemical Letters, 2024, 35(10): 109343-. doi: 10.1016/j.cclet.2023.109343
4. [4]
  Yuchen Zhang , Lifeng Ding , Zhenghe Xie , Xin Zhang , Xiaofeng Sui , Jian-Rong Li . Porous sorbents for direct capture of carbon dioxide from ambient air. Chinese Chemical Letters, 2025, 36(3): 109676-. doi: 10.1016/j.cclet.2024.109676
5. [5]
  Chao-Long Chen , Rong Chen , La-Sheng Long , Lan-Sun Zheng , Xiang-Jian Kong . Anchoring heterometallic cluster on P-doped carbon nitride for efficient photocatalytic nitrogen fixation in water and air ambient. Chinese Chemical Letters, 2024, 35(4): 108795-. doi: 10.1016/j.cclet.2023.108795
6. [6]
  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
7. [7]
  Wenjing Dai , Lan Luo , Zhen Yin . Interface reconstruction of hybrid oxide electrocatalysts for seawater oxidation. Chinese Journal of Structural Chemistry, 2025, 44(3): 100442-100442. doi: 10.1016/j.cjsc.2024.100442
8. [8]
  Gang Hu , Chun Wang , Qinqin Wang , Mingyuan Zhu , Lihua Kang . The controlled oxidation states of the H₄PMo₁₁VO₄₀ catalyst induced by plasma for the selective oxidation of methacrolein. Chinese Chemical Letters, 2025, 36(2): 110298-. doi: 10.1016/j.cclet.2024.110298
9. [9]
  Yi Zhang , Biao Wang , Chao Hu , Muhammad Humayun , Yaping Huang , Yulin Cao , Mosaad Negem , Yigang Ding , Chundong Wang . Fe–Ni–F electrocatalyst for enhancing reaction kinetics of water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100243-100243. doi: 10.1016/j.cjsc.2024.100243
10. [10]
  Yang Yang , Jing-Li Luo , Xian-Zhu Fu . Water-oxidation intermediates enabling electrochemical propylene epoxidation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100269-100269. doi: 10.1016/j.cjsc.2024.100269
11. [11]
  Gu Gong , Mengzhu Li , Ning Sun , Ting Zhi , Yuhao He , Junan Pan , Yuntao Cai , Longlu Wang . Versatile oxidized variants derived from TMDs by various oxidation strategies and their applications. Chinese Chemical Letters, 2024, 35(6): 108705-. doi: 10.1016/j.cclet.2023.108705
12. [12]
  Erzhuo Cheng , Yunyi Li , Wei Yuan , Wei Gong , Yanjun Cai , Yuan Gu , Yong Jiang , Yu Chen , Jingxi Zhang , Guangquan Mo , Bin Yang . Galvanostatic method assembled ZIFs nanostructure as novel nanozyme for the glucose oxidation and biosensing. Chinese Chemical Letters, 2024, 35(9): 109386-. doi: 10.1016/j.cclet.2023.109386
13. [13]
  Zhipeng Wan , Hao Xu , Peng Wu . Selective oxidation using in-situ generated hydrogen peroxide over titanosilicates. Chinese Journal of Structural Chemistry, 2024, 43(6): 100298-100298. doi: 10.1016/j.cjsc.2024.100298
14. [14]
  Huangjie Lu , Yingzhe Du , Peng Lin , Jian Lin . Separation of americium from lanthanides based on oxidation state control. Chinese Journal of Structural Chemistry, 2024, 43(10): 100344-100344. doi: 10.1016/j.cjsc.2024.100344
15. [15]
  Xian Yan , Huawei Xie , Gao Wu , Fang-Xing Xiao . Boosted solar water oxidation steered by atomically precise alloy nanocluster. Chinese Chemical Letters, 2025, 36(1): 110279-. doi: 10.1016/j.cclet.2024.110279
16. [16]
  Qinwei Lu , Jinjie Lu , Juying Lei , Xubiao Luo , Yanbo Zhou . Cyclodextrin-boosted photocatalytic oxidation for efficient bisphenol A removal. Chinese Chemical Letters, 2025, 36(3): 110017-. doi: 10.1016/j.cclet.2024.110017
17. [17]
  Zhiqiang Wang , Yajie Gao , Tianjun Wang , Wei Chen , Zefeng Ren , Xueming Yang , Chuanyao Zhou . Photocatalyzed oxidation of water on oxygen pretreated rutile TiO₂(110). Chinese Chemical Letters, 2025, 36(4): 110602-. doi: 10.1016/j.cclet.2024.110602
18. [18]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
19. [19]
  Yue Zhang , Xiaoya Fan , Xun He , Tingyu Yan , Yongchao Yao , Dongdong Zheng , Jingxiang Zhao , Qinghai Cai , Qian Liu , Luming Li , Wei Chu , Shengjun Sun , Xuping Sun . Ambient electrosynthesis of urea from carbon dioxide and nitrate over Mo₂C nanosheet. Chinese Chemical Letters, 2024, 35(8): 109806-. doi: 10.1016/j.cclet.2024.109806
20. [20]
  Qijun Tang , Wenguang Tu , Yong Zhou , Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(890)
HTML views(114)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142