Citation: Wang Maorui, Wu Yuzheng, Yao Jian, Deng Li, Pan Yingming, Huang Kebin, Tang Haitao. Triethylamine Promoted the C-C Bond Cleavage of α-Halo Ketones: α-Acetoxyaryl Ketone Synthesis[J]. Chinese Journal of Organic Chemistry, ;2019, 39(11): 3223-3229. doi: 10.6023/cjoc201904051 shu

Triethylamine Promoted the C-C Bond Cleavage of α-Halo Ketones: α-Acetoxyaryl Ketone Synthesis

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi 541004

Corresponding author: Huang Kebin, kbhuang@mailbox.gxnu.edu.cn Tang Haitao, httang@gxnu.edu.cn
Received Date: 22 April 2019
Revised Date: 7 June 2019
Available Online: 2 November 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21362002), and the Bagui Scholar Program of Guangxi Province of China (No. 2016A13)the Bagui Scholar Program of Guangxi Province of China 2016A13the National Natural Science Foundation of China 21362002

Figures(4)

The cleavage of C-C bonds is a key method for synthesis of useful intermediates. A novel amine-promoted C-C bond cleavage of α-halo ketones was reported. Oxidant-free and metal-free conditions are the striking features of the protocol. In this simple method, a variety of α-acetoxyaryl ketone compounds were prepared from commercially available α-halo ketones in good to excellent yields.
- cleavage of C-C bonds,
- α-halo ketones,
- oxidant-free and metal-free,
- α-acetoxyaryl ketone
1. [1]
  (a) Souillart, L.; Cramer, N. Chem. Rev. 2015, 115, 9410.
  (b) Chen, F.; Wang, T.; Jiao, N. Chem. Rev. 2014, 114, 8613.
  (c) Wang, T.; Jiao, N. Acc. Chem. Res. 2014, 47, 1137.
  (d) Murakami, M.; Ishida, N. J. Am. Chem. Soc. 2016, 138, 13759.
  (e) Tiwari, B.; Zhang, J.; Chi, Y. R. Angew. Chem. Int. Ed. 2012, 51, 1911.
  (f) Sai, M.; Yorimitsu, H.; Oshima, K. Angew. Chem. Int. Ed. 2011, 50, 3294.
  (g) Chen, W.-L.; Wu, S.-Y.; Mo, X.˗L.; Wei, L.˗X.; Liang, C.; Mo, D.˗L. Org. Lett. 2018, 20, 3527.
2. [2]
  (a) Tobisu, M.; Chatani, N. Chem. Soc. Rev. 2008, 37, 300.
  (b) Qin, C.; Shen, T.; Tang, C.; Jiao, N. Angew. Chem. Int. Ed. 2012, 51, 6971.
  (c) Qin, C.; Zhou, W.; Chen, F.; Ou, Y.; Jiao, N. Angew. Chem. Int. Ed. 2011, 50, 12595.
  (d) Klein, J. E. M. N.; Plietker, B. Org. Biomol. Chem. 2013, 11, 1271.
  (e) Kulinkovich, O. G. Chem. Rev. 2003, 103, 2597.
  (f) Bart, S. C.; Chirik, P. J. J. Am. Chem. Soc. 2003, 125, 886.
  (g) Seiser, T.; Cramer, N. J. Am. Chem. Soc. 2010, 132, 5340.
  (h) Seiser, T.; Saget, T.; Tran, D. N.; Cramer, N. Angew. Chem. Int. Ed. 2011, 50, 7740.
  (i) Jun, C-H. Chem. Soc. Rev., 2004, 33, 610.
3. [3]
  (a) Kumar, K. A. A.; Venkateswarlu, V.; Vishwakarma, R. A.; Sawant, S. D. Synthesis 2015, 47, 3161.
  (b) Zhang, J.; Jiang, J.; Li, Y.; Zhao, Y.; Wan, X. Org. Lett. 2013, 15, 3222.
4. [4]
  Liu, L.; Ishida, N.; Murakami, M. Angew. Chem. Int. Ed. 2012, 51, 2485. doi: 10.1002/anie.201108446
5. [5]
  (a) Wang, M.; Lu, J.; Zhang, X.; Li, L.; Li, H.; Luo, N.; Wang, F. ACS Catal. 2016, 6, 6086.
  (b) Liu, H.; Wang, M. Li, H.; Luo, N.; Xu, S.; Wang, F. J. Catal. 2017, 346, 170.
  (c) Wang, M.; Lu, J.; Li, L.; Li, H.; Liu, H.; Wang, F. J. Catal. 2017, 348, 160.
  (d) Anjum, A.; Srinivas, P. Chem. Lett. 2001, 9, 900.
  (e) Baruah, S.; Borthakur, S.; Gogoi, S. Chem. Commun. 2017, 53, 9133.
  (f) Nakamura, R.; Obora, Y.; Ishii, Y. Adv. Synth. Catal. 2009, 351, 1677.
  (g) Minisci, F.; Recupero, F.; Pedulli, G. F.; Lucarini, M. J. Mol. Catal. A 2003, 204~205, 63.
  (h) Minisci, F.; Recupero, F.; Fontana, F.; Bjϕrsvik, H˗R.; Liguori, L. Synlett. 2002, 610.
  (i) Sathyanarayana, P.; Ravi, O.; Muktapuram, P. R.; Bathula, S. R. Org. Biomol. Chem. 2015. 13, 9681.
6. [6]
  (a) Xu, L.; Wang, S.; Chen, B.; Li, M.; Hu, X.; Hu, B.; Jin, L.; Sun, N.; Shen, Z. Synlett. 2018, 1505.
  (b) Shaikh, T. M. A.; Sudalai, A. Eur. J. Org. Chem. 2008, 4877.
  (c) Santaniello, E.; Manzocchi, A.; Farachi, C. Synthesis 1980, 563.
  (d) Lee, J. C.; Lee, J. M. Synth. Commun. 2006, 36, 1071.
  (e) Lee, J. C.; Choi, J. H.; Lee, Y. C. Synlett. 2001, 1563.
7. [7]
  (a) Liu, H.; Li, H.; Lu, J.; Zeng, S.; Wang, M.; Luo, N.; Xu, S.; Wang, F. ACS Catal. 2018, 8, 4761.
  (b) Hirashima, S˗i.; Nobuta, T.; Tada, N.; Itoh, A. Synlett 2009, 2017.
  (c) Yamaguchi, T.; Matsusaki, Y.; Tada, N.; Miura, T.; Itoh, A. Photochem. Photobiol. Sci. 2013, 12, 417.
8. [8]
  (a) Sathyanarayana, P.; Upare, A.; Ravi, O.; Muktapuram, P. R.; Bathula, S. R. RSC Adv. 2016, 6, 22749.
  (b) Angeles, N. A.; Villavicencio, F.; Guadarrama, C.; Corona, D.; Cuevas˗Yañez, E. J. Braz. Chem. Soc. 2010, 21, 905.
  (c) Cao, L.; Ding, J.; Gao, M.; Wang, Z.; Li, J.; Wu, A. Org. Lett. 2009, 11, 3810.
  (d) Rajendar, K.; Kant, R.; Narender, T. Adv. Synth. Catal. 2013, 355, 3591.
9. [9]
  (a) Caputo, D. F. J.; Arroniz, C.; Dürr, A. B.; Mousseau, J. J.; Stepan, A. F.; Mansfield, S. J.; Anderson, E. A. Chem. Sci. 2018, 9, 5295.
  (b) Ram, R. N.; Soni, V. K. J. Org. Chem. 2015, 80, 8922.
  (c) Luo, J.; Zhang, X.; Zhang, J. ACS Catal. 2015, 5, 2250.
  (d) Xu, G˗C.; Yu, H˗L.; Zhang, X˗Y.; Xu, J˗H. ACS Catal. 2012, 2, 2566.
  (e) Neumann, M.; Füldner, S.; König, B.; Zeitler, K. Angew. Chem. Int. Ed. 2011, 50, 951.
  (f) Jiang, H.; Bak, J. R.; López˗Delgado, F. J.; Jørgensen, K. A. Green Chem. 2013, 15, 3355.
  (g) Zhou, F.; Hu, X.; Gao, M.; Cheng, T.; Liu, G. Green Chem. 2016, 18, 5651.
  (h) Toma, T.; Shimokawa, J.; Fukuyama, T. Org. Lett. 2007, 9, 3195.
10. [10]
  Yu, S.; Liu, S.; Lan, Y.; Wan, B.; Li, X. J. Am. Chem. Soc. 2015, 137, 1623. doi: 10.1021/ja511796h
11. [11]
  (a) Tong, W.; Li, W.˗H.; He, Y.; Mo, Z.˗Y.; Tang, H.˗T.; Wang, H.˗S.; Pan, Y.˗M. Org. Lett. 2018, 20, 2494.
  (b) He, Y.; Wang, Y.; Liang, X.; Huang, B.; Wang, H.; Pan, Y.˗M.; Org. Lett. 2018, 20, 7117.
  (c) Huang, X.˗Y.; Ding, R.; Mo, Z.˗Y.; Xu, Y.˗L.; Tang, H.˗T.; Wang, H.˗S.; Chen, Y.˗Y.; Pan, Y.˗M. Org. Lett. 2018, 20, 4819.
  (d) Zhang, B.; Studer, A. Chem. Soc. Rev. 2015, 44, 3505.
  (e) Wang, X.; Xiong, W.; Huang, Y.; Zhu, J.; Hu, Q.; Wu, W.; Jiang, H. Org. Lett. 2017, 19, 5818.
  (f) Hu, W.; Li, J.; Xu, Y.; Li, J.; Wu, W.; Liu, H.; Jiang, H. Org. Lett. 2017, 19, 678.
  (g) Peng, J.; Gao, Y.; Hu, W.; Gao, Y.; Hu, M.; Wu, W.; Ren, Y.; Jiang, H. Org. Lett. 2016, 18, 5924.
12. [12]
  (a) Tan, L.; Chen, C.; Liu, W. Beilstein J. Org. Chem. 2017, 13, 1079.
  (b) Jia, W˗G.; Zhang, H.; Li, D˗D.; Yan, L˗Q. RSC Adv. 2016, 6, 27590.
1. [1]
  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
2. [2]
  Yuwei Liang , Jianwei Huang , Zhiqiang Zhang , Qinghong Yang , Aiwen Lei , Hong Yi . Electrochemical Mn-catalyzed nitrogenation of alkynes to nitriles via C≡C bonds cleavage. Chinese Chemical Letters, 2026, 37(4): 111166-. doi: 10.1016/j.cclet.2025.111166
3. [3]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
4. [4]
  Junyou Ding , Xiaotong Li , Hongmin Lin , Bochao Ye , Xing Zhou , Feihu Cui , Yingming Pan , Haitao Tang . Highly regioselective hydrogermylation of unsaturated C-C bonds over ligand-control single atom palladium catalysts. Chinese Chemical Letters, 2025, 36(11): 111286-. doi: 10.1016/j.cclet.2025.111286
5. [5]
  Chunxiu Yu , Zelin Wu , Hongle Shi , Lingyun Gu , Kexin Chen , Chuan-Shu He , Yang Liu , Heng Zhang , Peng Zhou , Zhaokun Xiong , Bo Lai . Insights into the electron transfer mechanisms of peroxydisulfate activation by modified metal-free acetylene black for degradation of sulfisoxazole. Chinese Chemical Letters, 2024, 35(8): 109334-. doi: 10.1016/j.cclet.2023.109334
6. [6]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
7. [7]
  Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
8. [8]
  Kexin Yin , Jingren Yang , Yanwei Li , Qian Li , Xing Xu . Metal-free diatomaceous carbon-based catalyst for ultrafast and anti-interference Fenton-like oxidation. Chinese Chemical Letters, 2024, 35(12): 109847-. doi: 10.1016/j.cclet.2024.109847
9. [9]
  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
10. [10]
  Lingdan Kong , Pingping Huang , Feng Yuan , Yue Zhang , Xiaoqian Shi , Kang Han , Keke Liu , Qing Xu , Wenjing Zhang , Tom Lawson , Xiaoru Xia , Yong Liu , Yuepeng Jin . A metal-free bionic nanozyme for efficient inhibition of cancer recurrence and metastasis following photothermal therapy. Chinese Chemical Letters, 2025, 36(9): 111030-. doi: 10.1016/j.cclet.2025.111030
11. [11]
  Congxu Wang , Xuan Xie , Feng Qiu , Lei Zhu , Imran Shakir , Yuxi Xu . Recent advances in photocatalytic overall production of hydrogen peroxide from metal-free photocatalysts. Chinese Chemical Letters, 2026, 37(1): 111604-. doi: 10.1016/j.cclet.2025.111604
12. [12]
  Tong Yue , Jun-Bo Wang , Xin-Yue Wang , Ming-Yi Huang , Mo Zhang , Zhan-Hui Zhang . Metal-free carbon quantum dots as photocatalyst for phosphonation of undirected heteroaryl compounds. Chinese Chemical Letters, 2026, 37(8): 112050-. doi: 10.1016/j.cclet.2025.112050
13. [13]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
14. [14]
  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
15. [15]
  Lingdan Kong , Pingping Huang , Feng Yuan , Yue Zhang , Xiaoqian Shi , Kang Han , Keke Liu , Qing Xu , Wenjing Zhang , Tom Lawson , Xiaoru Xia , Yong Liu , Yuepeng Jin . Corrigendum to “A metal-free bionic nanozyme for efficient inhibition of cancer recurrence and metastasis following photothermal therapy” [Chinese Chemical Letters 36 (2025) 111030]. Chinese Chemical Letters, 2026, 37(9): 112822-. doi: 10.1016/j.cclet.2026.112822
16. [16]
  Wentian Zheng , Jiachen Wang , Yifan Ren , Yanbiao Liu . Integrated electrochemical and catalytic system with metal-free CNT membrane electrode for efficient aniline degradation via peracetic acid activation. Chinese Chemical Letters, 2026, 37(10): 112462-. doi: 10.1016/j.cclet.2026.112462
17. [17]
  Jiaxuan YANG , Chenfa DENG , Jingyang LIU , Chenzexi XU , Hongxin CHEN , Yahui ZHU , Ying LI , Shuhua WANG , Rongping ZHOU , Chao CHEN . Advances in selective hydrogenation of α, β-unsaturated aldehydes/ketones catalyzed by metal-organic frameworks and their derivatives: A review. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 1973-2010. doi: 10.11862/CJIC.20250175
18. [18]
  Xinghao Cai , Chen Ma , Ying Kang , Yuqiang Ren , Xue Meng , Wei Lu , Shiming Fan , Shouxin Liu . Nickel-catalyzed C(sp²)–H alkynylation of free α-substituted benzylamines using a transient directing group. Chinese Chemical Letters, 2025, 36(10): 110901-. doi: 10.1016/j.cclet.2025.110901
19. [19]
  Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp³) and C(sp)-C(sp²) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
20. [20]
  Xiaodan Wang , Yingnan Liu , Zhibin Liu , Zhongjian Li , Tao Zhang , Yi Cheng , Lecheng Lei , Bin Yang , Yang Hou . Highly efficient electrosynthesis of H₂O₂ in acidic electrolyte on metal-free heteroatoms co-doped carbon nanosheets and simultaneously promoting Fenton process. Chinese Chemical Letters, 2024, 35(7): 108926-. doi: 10.1016/j.cclet.2023.108926

Get Citation

PDF

XML

Metrics

PDF Downloads(35)
Abstract views(1788)
HTML views(183)

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