Citation: Su Yingpeng, Shi Ya, Chang Bingbing, Wu Lili, Chong Siying, Zhang Weigang, Huang Danfeng, Wang Kehu, Hu Yulai. Chlorination of α-Cyanoketones and 1, 3-Dicarbonyl Compounds by Using Trichloroisocyanuric Acid as Chlorine Source[J]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1454-1461. doi: 10.6023/cjoc201712042 shu

Chlorination of α-Cyanoketones and 1, 3-Dicarbonyl Compounds by Using Trichloroisocyanuric Acid as Chlorine Source

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Corresponding author: Su Yingpeng, suyp51@nwnu.edu.cn
Received Date: 28 December 2017
Revised Date: 28 December 2017
Available Online: 28 June 2018
Fund Project: the Gansu Provincial Science and Technology Program 17JR5RA073Project supported by the National Natural Science Foundation of China (Nos. 21362033, 21502154) and the Gansu Provincial Science and Technology Program (No. 17JR5RA073)the National Natural Science Foundation of China 21362033the National Natural Science Foundation of China 21502154

Figures(3)

The α-chlorination of α-substituted-α-cyano ketone compounds and 1, 3-dicabonyl compounds is described. Using 0.34 equiv. trichloroisocyanuric acid as chlorine source, the chlorination can efficiently access at room temperature in a mild condition without additional oxidant or base. The chloride products can be obtained in a higher yield.
- trichloroisocyanuric acid,
- chlorination reaction,
- α-cyanoketone
1. [1]
  Roman, B. I.; Kimpe, N. D.; Stevens, C. V. Chem. Rev. 2010, 110, 5914. doi: 10.1021/cr900409h
2. [2]
  Dickenson, E. V.; Summers, R. S.; Croue, J.-P.; Gallard, H. Environ.Sci.Technol. 2008, 42, 3226. doi: 10.1021/es0711866
3. [3]
4. [4]
  Glória, P. M. C.; Prabhakar, S.; Lobo, A. M. Tetrahedron Lett. 2008, 49, 7355. doi: 10.1016/j.tetlet.2008.10.047
5. [5]
  Surmont, R.; Verniest, G.; Kimpe, N. D. Org. Lett. 2010, 12, 4648. doi: 10.1021/ol1019713
6. [6]
  Shi, M.; Zhan, G.; Zhou, S.; Du, W.; Chen, Y. Org. Lett. 2016, 18, 6480. doi: 10.1021/acs.orglett.6b03384
7. [7]
  Tang, L.; Negrerie, D. Z.; Du, Y.; Zhao, K. Synthesis 2014, 46, 1621. doi: 10.1055/s-00000084
8. [8]
  Umland, K-D.; Mayer, C.; Kirsch, S. F. Synlett 2014, 25, 813. doi: 10.1055/s-00000083
9. [9]
  Tilstam, U.; Weinmann, H. Org.Process Res.Dev. 2002, 6, 384. doi: 10.1021/op010103h
10. [10]
  Luca, L. D.; Giacomelli, G.; Porcheddu, A. Org.Lett. 2001, 3, 3041. doi: 10.1021/ol016501m
11. [11]
  Ashtekar, K. D.; Marzijarani, N. S.; Jaganathan, A.; Holmes, D.; Jackson, J. E.; Borhan, B. J.Am.Chem.Soc. 2014, 136, 13355. doi: 10.1021/ja506889c
12. [12]
  Zhang, W.; Su, Y.; Wang, K.-H.; Wu, L.; Chang, B.; Shi, Y.; Huang, D; Hu, Y. Org.Lett. 2017, 19, 376. doi: 10.1021/acs.orglett.6b03582
13. [13]
  Luca, L. D.; Giacomelli, G. Synlett 2004, 2180.
14. [14]
  Luca, L. D.; Giacomelli, G.; Nieddu, G. Synlett 2005, 223.
15. [15]
  Vo, T. T.; Zhang, J.; Parrish, D. A.; Twamley, B.; Shreeve, J. M. J. Am.Chem.Soc. 2013, 135, 11787. doi: 10.1021/ja406629g
16. [16]
  (a) Acharya, J. ; Gupta, A. K. ; Shakya, P. D. ; Kaushik, M. P. Tetrahedron Lett. 2005, 46, 5293.
  (b)Varaprath, S. ; Stutts, D. H. J. Organomet. Chem. 2007, 692, 1892.
17. [17]
  (a) Oyley, J. M. D. ; Aliev, A. E. ; Sheppard, T. D. Angew. Chem., Int. Ed. 2014, 53, 10747.
  (b) Mishra, A. K. ; Nagarajaiah, H. ; Moorthy, J. N. Eur. J. Org. Chem. 2015, 2733.
  (c) Lied, F. ; Lerchen, A. ; Knecht, T. ; Mu?ck-Lichtenfeld, C. ; Glorius, F. ACS Catal. 2016, 6, 7839.
18. [18]
  Combe, S. H.; Hosseini, A.; Parra, A.; Schreiner, P. R. J.Org. Chem. 2017, 82, 2407. doi: 10.1021/acs.joc.6b02829
19. [19]
  Mendonça, G. F.; Sindra, H. C.; Almeida, L. S.; Esteves, P. M.; Mattos, M. C. S. Tetrahedron Lett. 2009, 50, 473. doi: 10.1016/j.tetlet.2008.11.045
20. [20]
  Chong, S.; Su, Y.; Wu, L.; Zhang, W.; Ma, J.; Chen, X.; Huang, D.; Wang, K.-H.; Hu, Y. Synthesis 2016, 1359.
21. [21]
  Yu, W.; Du, Y.; Zhao, K. Org. Lett. 2009, 11, 2956.
22. [22]
  Smallridge, A. J.; Ten, A.; Trewhella, M. A. Tetrahedron Lett. 1998, 39, 5121. doi: 10.1016/S0040-4039(98)00945-9
23. [23]
  (a) Grill, J. M. ; Ogle, J. W. ; Miller, S. A. J. Org. Chem. 2006, 71, 9291.
  (b) Kim, S. H. ; Kim, K. H. ; Hong, S. H. Angew. Chem., Int. Ed. 2014, 53, 771.
1. [1]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
2. [2]
  Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
3. [3]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
4. [4]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
5. [5]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
6. [6]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
7. [7]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
8. [8]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
9. [9]
  Tongyan Yu , Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070
10. [10]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
11. [11]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
12. [12]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
13. [13]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
14. [14]
  Weikang Wang , Yadong Wu , Jianjun Zhang , Kai Meng , Jinhe Li , Lele Wang , Qinqin Liu . 三聚氰胺泡沫支撑的S型硫铟锌镉/硫掺杂氮化碳异质结的绿色H₂O₂合成：协同界面电荷转移调控与局域光热效应. Acta Physico-Chimica Sinica, 2025, 41(8): 100093-. doi: 10.1016/j.actphy.2025.100093
15. [15]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
16. [16]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
17. [17]
  Xinxin Wu . 基础有机化学教学中自由基重排反应的课程设计及其课程思政元素的融入. University Chemistry, 2025, 40(6): 316-325. doi: 10.12461/PKU.DXHX202408055
18. [18]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
19. [19]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
20. [20]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024

Get Citation

PDF

XML

Metrics

PDF Downloads(18)
Abstract views(2666)
HTML views(461)

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