Citation: Li Zhibin, Sun Qi, Qian Peng, Hu Kangfei, Zha Zhenggen, Wang Zhiyong. Electrochemical synthesis of α, α-dihaloacetophenones from terminal alkyne derivatives[J]. Chinese Chemical Letters, ;2020, 31(7): 1855-1858. doi: 10.1016/j.cclet.2020.02.030 shu

Electrochemical synthesis of α, α-dihaloacetophenones from terminal alkyne derivatives

Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry & Center for Excellence in Molecular Synthesis of Chinese Academy of Sciences, Collaborative Innovation Center of Suzhou Nano Science and Technology & School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, China

zgzha@ustc.edu.cn

zwang3@ustc.edu.cn

Received Date: 14 October 2019
Revised Date: 3 February 2020
Accepted Date: 17 February 2020
Available Online: 18 February 2020

Figures(4)

By virtue of electrochemistry, a series of α, α-dihaloacetophenones were easily obtained with good to excellent yields. This electrochemical procedure was taken in a divided cell with constant current in aqueous media. The reaction can be carried out smoothly at room temperature under metal and oxidant free condition, which provides an eco-friendly synthesis for the α, α-dihaloacetophenone derivatives.
- Electrochemistry,
- Alkyne derivatives,
- α, α-Dihaloacetophenones,
- Divided cell,
- Oxidant free
1. [1]
  (a) E.M. Antunes, A.F. Afolayan, M.T. Chiwakata, et al., Phytochemistry 72 (2011) 769-772;
  (b) R. Teraoka, Y. Matsushima, I. Sugimoto, et al., Chem. Pharm. Bull. 57 (2009) 1343-1347.
2. [2]
  (a) S. Araki, T. Hirashita, K. Shimizu, T. Ikeda, Y. Butsugan, Tetrahedron 52 (1996) 2803-2816;
  (b) D. Shanmugapriya, R. Shankar, G. Satyanarayana, et al., Synlett (2008) 2945-2950;
  (c) A. Raghunadh, S.B. Meruva, N.A. Kumar, et al., Synthesis (2012) 283-289;
  (d) J. Jiang, H. Zou, Q. Dong, et al., J. Org. Chem. 81 (2016) 51-56;
  (e) C. Peppe, R.P. das Chagas, R.A. Burrow, J. Organomet. Chem. 693 (2008) 3441-3445;
  (f) X. Wang, S.A. Zhang, Chin. J. Chem. 30 (2012) 96-102;
  (g) J.M. Concello'n, H. Rodríguez-Solla, C. Concello'n, P. Díaz, Synlett (2006) 837-840.
3. [3]
  (a) D. Vrazic, M. Jereb, K. Laali, Kenneth, S. Stavber, Molecules 18 (2013) 74-96;
  (b) A.G. Hiegel, K.B. Peyton, Synth. Commun. 15 (1985) 385-392;
  (c) J.G. Aston, J.D. Newkirk, D.M. Jenkins, D. Julian, Organic Synth. 23 (1943) 48;
  (d) A. Raghunadh, S.B. Meruva, N.A. Kumar, et al., Synthesis (2012) 283-289;
  (e) K.J. Satinder, C. Deepak, P. Satya, G. Rajive, Synth. Commun. 36 (2006) 2877-2881;
  (f) Z. Zheng, B. Han, C. Peng, J. Niu, A. Wang, Tetrahedron 70 (2014) 9814-9818;
  (g) Z. Chen, B. Zhou, H. Cai, W. Zhu, X. Zou, Green Chem. 11 (2009) 275-278.
4. [4]
  (a) X. Zhang, Y. Wu, Y. Zhang, et al., Tetrahedron 73 (2017) 4513-4518;
  (b) J. Liu, W. Li, C. Wang, Y. Li, Z. Li, Tetrahedron Lett. 52 (2011) 4320-4323;
  (c) C. Wu, X. Xin, Z. Fu, et al., Green Chem. 19 (2017) 1983-1989;
  (d) F. Lucie, B. Jeremy, P. Bhavana, G. Fabrice, H. Sachin, J. Org. Chem. 83 (2018) 7366-7372;
  (e) A.H. Gene, D.B. Christopher, R. Brendt, Synth. Commun. 33 (2003) 1997-2002;
  (f) C. Bryant, L. John, K. Claudia, et al., Tetrahedron Lett. 56 (2015) 4124-4127;
  (g) D.M. Maan, K.R. Kamal, P. Prodeep, Synth. Commun. 47 (2017) 2330-2341.
5. [5]
  (a) M. Sridhar, J. Raveendra, M.K.K. Reddy, G.K. Reddy, S.V. Venkata, Tetrahedron Lett. 54 (2013) 3993-3996;
  (b) C. Ye, J.M. Shreeve, J. Org. Chem. 69 (2004) 8561-8563;
  (c) P. Palash, S.G. Krishnanka, K. Saikat, C. Nirbhik, K.M. Dilip, Chem. Commun. 47 (2011) 6933-6935;
  (d) N. Tomoya, H. Shin-ichi, T. Norihiro, M. Tsuyoshi, I. Akichika, Tetrahadron Lett. 51 (2010) 4576-4578;
  (e) J. Wang, Q. Jiang, C. Guo, Synth. Commun. 44 (2014) 3130-3138;
  (f) S.A. Rather, A. Kumarab, Q.N. Ahmed, Chem. Commun. 55 (2019) 4511-4514.
6. [6]
  A.R. Moises, Z. Ivann, F.O. Horacio, R. Moises, J. Org. Chem. 81(2016) 9515-9519. doi: 10.1021/acs.joc.6b02044
7. [7]
  D.C.G. Rafael, A. Anees, M. Gustavo, C.B.B. Antonio, Chem. Eur. J. 23(2017) 16980-16984. doi: 10.1002/chem.201704609
8. [8]
  (a) M. Bi, P. Qian, Y. Wang, Z. Zha, Z. Wang, Chin. Chem. Lett. 28 (2017) 1159-1162;
  (b) R. Francke, R.D. Little, Chem. Soc. Rev. 43 (2014) 2492-2521;
  (c) C. Zeng, L. Hu, J. Zeng, R. Zhong, Chin. Chem. Lett. 18 (2007) 130-132;
  (d) M. Yan, Y. Kawamata, P.S. Baran, Chem. Rev. 117 (2017) 13230-13319;
  (e) A. Wiebe, T. Gieshoff, S. Mohle, et al., Angew. Chem. Int. Ed. 57 (2018) 5594-5619;
  (f) J. Zhang, H. Wang, Y. Chen, et al., Chin. Chem. Lett. (2019), doi: http://dx.doi.org/10.1016/j.cclet.2019.11.037.
9. [9]
  (a) J.J. Renard, H.I. Bolker, Chem. Rev. 76 (1976)487-508;
  (b) D.S. Davis, Ind. Eng. Chem. 34(5) (1942)624-624.
10. [10]
  (a) C.S. Gardner, R.C. DeLanson, J. Am. Chem. Soc. 94(9) (1972) 3195-3200;
  (b) D.S. John, E.M. Corey, A.R. Lynn, Environ. Sci. Technol. 44 (2010) 3357-3362.
1. [1]
  Xue Xin , Qiming Qu , Islam E. Khalil , Yuting Huang , Mo Wei , Jie Chen , Weina Zhang , Fengwei Huo , Wenjing Liu . Hetero-phase zirconia encapsulated with Au nanoparticles for boosting electrocatalytic nitrogen reduction. Chinese Chemical Letters, 2024, 35(5): 108654-. doi: 10.1016/j.cclet.2023.108654
2. [2]
  Zixuan Guo , Xiaoshuai Han , Chunmei Zhang , Shuijian He , Kunming Liu , Jiapeng Hu , Weisen Yang , Shaoju Jian , Shaohua Jiang , Gaigai Duan . Activation of biomass-derived porous carbon for supercapacitors: A review. Chinese Chemical Letters, 2024, 35(7): 109007-. doi: 10.1016/j.cclet.2023.109007
3. [3]
  Qiang Cao , Xue-Feng Cheng , Jia Wang , Chang Zhou , Liu-Jun Yang , Guan Wang , Dong-Yun Chen , Jing-Hui He , Jian-Mei Lu . Graphene from microwave-initiated upcycling of waste polyethylene for electrocatalytic reduction of chloramphenicol. Chinese Chemical Letters, 2024, 35(4): 108759-. doi: 10.1016/j.cclet.2023.108759
4. [4]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
5. [5]
  Li Li , Zhi-Xin Yan , Chuan-Kun Ran , Yi Liu , Shuo Zhang , Tian-Yu Gao , Long-Fei Dai , Li-Li Liao , Jian-Heng Ye , Da-Gang Yu . Electro-reductive carboxylation of CCl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO₂. Chinese Chemical Letters, 2024, 35(12): 110104-. doi: 10.1016/j.cclet.2024.110104
6. [6]
  Yan-Jiang Li , Shu-Lei Chou , Yao Xiao . Detecting dynamic structural evolution based on in-situ high-energy X-ray diffraction technology for sodium layered oxide cathodes. Chinese Chemical Letters, 2025, 36(2): 110389-. doi: 10.1016/j.cclet.2024.110389
7. [7]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
8. [8]
  Yongming Zhu , Huili Hu , Yuanchun Yu , Xudong Li , Peng Gao . Construction and Practice on New Form Stereoscopic Textbook of Electrochemistry for Energy Storage Science and Engineering: Taking Basic Course of Electrochemistry as an Example. University Chemistry, 2024, 39(8): 44-47. doi: 10.3866/PKU.DXHX202312086
9. [9]
  Yifei Cheng , Jiahui Yang , Wei Shao , Wanqun Zhang , Wanqun Hu , Weiwei Li , Kaiping Yang . Learning Goes Beyond the Written Word: Practical Insights from the “Leaf Electroplating” Popular Science Experiment. University Chemistry, 2024, 39(9): 319-327. doi: 10.3866/PKU.DXHX202310033
10. [10]
  Kuaibing Wang , Honglin Zhang , Wenjie Lu , Weihua Zhang . Experimental Design and Practice for Recycling and Nickel Content Detection from Waste Nickel-Metal Hydride Batteries. University Chemistry, 2024, 39(11): 335-341. doi: 10.12461/PKU.DXHX202403084
11. [11]
  Cen Zhou , Biqiong Hong , Yiting Chen . Application of Electrochemical Techniques in Supramolecular Chemistry. University Chemistry, 2025, 40(3): 308-317. doi: 10.12461/PKU.DXHX202406086
12. [12]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
13. [13]
  Yunan Yuan , Zhimin Luo , Jie Chen , Chaoliang He , Kai Hao , Huayu Tian . Constructing thermoresponsive PNIPAM-based microcarriers for cell culture and enzyme-free cell harvesting. Chinese Chemical Letters, 2024, 35(7): 109549-. doi: 10.1016/j.cclet.2024.109549
14. [14]
  Linbao Zhang , Weisi Guo , Shuwen Wang , Ran Song , Ming Li . Electrochemical Oxidation of Sulfides to Sulfoxides. University Chemistry, 2024, 39(11): 204-209. doi: 10.3866/PKU.DXHX202401009
15. [15]
  Tao Wei , Jiahao Lu , Pan Zhang , Qi Zhang , Guang Yang , Ruizhi Yang , Daifen Chen , Qian Wang , Yongfu Tang . An intermittent lithium deposition model based on bimetallic MOFs derivatives for dendrite-free lithium anode with ultrahigh areal capacity. Chinese Chemical Letters, 2024, 35(8): 109122-. doi: 10.1016/j.cclet.2023.109122
16. [16]
  Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
17. [17]
  Jian-Rong Li , Jieying Hu , Lai-Hon Chung , Jilong Zhou , Parijat Borah , Zhiqing Lin , Yuan-Hui Zhong , Hua-Qun Zhou , Xianghua Yang , Zhengtao Xu , Jun He . Insight into stable, concentrated radicals from sulfur-functionalized alkyne-rich crystalline frameworks and application in solar-to-vapor conversion. Chinese Journal of Structural Chemistry, 2024, 43(8): 100380-100380. doi: 10.1016/j.cjsc.2024.100380
18. [18]
  Fangwen Peng , Zhen Luo , Yingjin Ma , Haibo Ma . Theoretical study of aromaticity reversal in dimethyldihydropyrene derivatives. Chinese Journal of Structural Chemistry, 2024, 43(5): 100273-100273. doi: 10.1016/j.cjsc.2024.100273
19. [19]
  Weiyu Chen , Zenghui Li , Chenguang Zhao , Lisha Zha , Junfeng Shi , Dan Yuan . Enzyme-modulate conformational changes in amphiphile peptide for selectively cell delivery. Chinese Chemical Letters, 2024, 35(12): 109628-. doi: 10.1016/j.cclet.2024.109628
20. [20]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(843)
HTML views(76)

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