Efficient Hydrolysis of Haloalkynes to α-Haloketones in Ionic Liquid
- Corresponding author: Xiang Jiannan, jnxiang@hnu.edu.cn
Citation:
Fu Wenqiang, Tan Ping, Deng Wei, Xiang Jiannan. Efficient Hydrolysis of Haloalkynes to α-Haloketones in Ionic Liquid[J]. Chinese Journal of Organic Chemistry,
;2017, 37(6): 1501-1505.
doi:
10.6023/cjoc201610031
(a) Erian, A. W.; Sherif, S. M.; Gaber, H. M. Molecules 2003, 8, 793.
(b) Zhang, H.; Wei, Q.; Wei, S.; Qu, J.; Wang, B. Eur. J. Org. Chem. 2016, 3373.
De Kimpe, N.; Verhé, R. The Chemistry of α-Haloketones, α-Haloaldehydes and α-Haloimines, Ed.: Patai, S., Wiley, Chichester, UK, 1988, pp. 1~119.
(a) Ostrowski, T.; Golankiewicz, B.; De Clercq, E.; Andrei, G.; Snoeck, R. Eur. J. Med. Chem. 2009, 44, 3313.
(b) Conde, S.; Pérez, D. I.; Martínez, A.; Perez, C.; Moreno, F. J. J. Med. Chem. 2003, 46, 4631.
(a) Morton, H. E.; Leanna, M. R. Tetrahedron Lett. 1993, 34, 4481.
(b) Patil, R. D.; Joshi, G.; Adimurthy, S.; Ranu, B. C. Tetrahedron Lett. 2009, 50, 2529.
(c) Tanemura, K.; Suzuki, T.; Nishida, Y.; Satsumabayashi, K.; Horaguchi, T. Chem. Commun. 2004, 470.
(d) Meshram, H. M.; Reddy, P. N.; Vishnu, P.; Sadashiv, K.; Yadav, J. S. Tetrahedron Lett. 2006, 47, 991.
(e) Pravst, I.; Zupan, M.; Stavber, S. Tetrahedron 2008, 64, 5191.
(f) Kosower, E. M.; Wu, G. S. J. Org. Chem. 1963, 28, 633.
(g) Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Fujisaki, S.; Maeno, K.; Okamoto, T. Synthesis 1988, 545.
(h) Dieter, R. K.; Nice, L. E.; Velu, S. E. Tetrahedron Lett. 1996, 37, 2377.
Xie, L.; Wu, Y.; Yi, W.; Zhu, L.; Xiang, J.; He, W. J. Org. Chem. 2013, 78, 9190.
doi: 10.1021/jo401437w
Zou, H.; He, W.; Dong, Q.; Wang, R.; Yi, N.; Jiang, J.; Peng, D.; He, W. Eur. J. Org.Chem. 2016, 116.
(a) Chen, Z.; Ye, D.; Ye, M.; Zhou, Z.; Li, S.; Liu, L. Tetrahedron Lett. 2014, 55, 1373.
(b) Zeng, M.; Huang, R.; Li, W.; Liu, X.; He, F.; Zhang, Y.; Xiao, F. Tetrahedron Lett. 2016, 72, 3818.
(a) Olivier-Bourbigou, H.; Magna, L.; Morvan, D. Appl. Catal. A: Gen. 2010, 373, 1.
(b) Hu, Y.; Guo, Z.; Lue, B. M.; Xu, X. J. Agric. Food Chem. 2009, 57, 3845.
(c) Tzani, A.; Douka, A.; Papadopoulos, A.; Pavlatou, E. A.; Voutsas, E.; Detsi, A. ACS Sustainable Chem. Eng. 2013, 1, 1180.
Wong, W.; Ho, K.; Lee, L.; Lam, K.; Zhou, Z.; Chan, T.; Wong, K. ACS Catal. 2011, 1, 116.
doi: 10.1021/cs100016h
Wei, Q. L.; Zhang, S. S.; Gao, J.; Li, W. H.; Xu, L. Z.; Yu, Z. G. Bioorg. Med. Chem. 2006, 14, 7146.
doi: 10.1016/j.bmc.2006.06.065
Reddy Bodireddy, M.; Gangi, R. N. C. Synth. Commun. 2013, 43, 2603.
doi: 10.1080/00397911.2012.725264
Guan, X.; AlMisbaa, Z.; Huang, K. Arabian J. Chem. 2015, 8, 892.
doi: 10.1016/j.arabjc.2014.01.024
Sugiura, A.; Kepner, R. E.; Webb, A. D. J. Org. Chem. 1962, 27, 773.
doi: 10.1021/jo01050a020
Jiang, Q.; Sheng, W.; Guo, C. Green Chem. 2013, 15, 2175
doi: 10.1039/c3gc40515j
Rosenmund, K. W. Chem. Ber. 1957, 90, 1922.
doi: 10.1002/(ISSN)1099-0682
Lapointe, D.; Markiewicz, T.; Whipp, C. J.; Toderian, A.; Fagnou, K. J. Org. Chem. 2011, 76, 749.
doi: 10.1021/jo102081a
Judefind, W. L. J. Am. Chem. Soc. 1920, 42, 1043.
doi: 10.1021/ja01450a019
Arrieta, A. Synth. Commun. 1984, 14, 939.
doi: 10.1080/00397918408063764
Suzuki, M. Yakugaku Zasshi 1952, 72, 305.
doi: 10.1248/yakushi1947.72.3_305
Antunes, H.; Fardelone, L. C.; Rodrigues, J. A. R.; Moran, P. J. S. Tetrahedron: Asymmetry 2004, 15, 2615.
doi: 10.1016/j.tetasy.2004.07.029
Daojuan Cheng , Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105
Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
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
Yiling Wu , Peiyao Jin , Shenyue Tian , Ji Zhang . The Star of Sugar Substitutes: An Interview of Erythritol. University Chemistry, 2024, 39(9): 22-27. doi: 10.12461/PKU.DXHX202404034
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
Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
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
Yingran Liang , Fei Wang , Jiabao Sun , Hongtao Zheng , Zhenli Zhu . Construction and Application of a New Experimental Device for Determination of Alkaline Metal Elements by Plasma Atomic Emission Spectrometry Based on Solution Cathode Glow Discharge: An Alternative Approach for Fundamental Teaching Experiments in Emission Spectroscopy. University Chemistry, 2024, 39(5): 380-387. doi: 10.3866/PKU.DXHX202312024
Yang Chen , Peng Chen , Yuyang Song , Yuxue Jin , Song Wu . Application of Chemical Transformation Driven Impurity Separation in Experiments Teaching: A Novel Method for Purification of α-Fluorinated Mandelic Acid. University Chemistry, 2024, 39(6): 253-263. doi: 10.3866/PKU.DXHX202310077
Shanying Chen , Kangning Huo , Ke Qi , Jingyi Li , Shuxin Li , Yunchao Li . A Novel Colloid Electrophoresis Experiment with the Characteristics of Resource Recycling and Inquiry-Driven Experimental Design. University Chemistry, 2024, 39(5): 274-286. doi: 10.3866/PKU.DXHX202311067
Mei Yan , Rida Feng , Yerdos·Tohtarkhan , Biao Long , Li Zhou , Chongshen Guo . Expansion and Extension of Liquid Saturated Vapor Measurement Experiment. University Chemistry, 2024, 39(3): 294-301. doi: 10.3866/PKU.DXHX202308103
Zhicheng JU , Wenxuan FU , Baoyan WANG , Ao LUO , Jiangmin JIANG , Yueli SHI , Yongli CUI . MOF-derived nickel-cobalt bimetallic sulfide microspheres coated by carbon: Preparation and long cycling performance for sodium storage. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 661-674. doi: 10.11862/CJIC.20240363
Xuan Zhou , Yi Fan , Zhuoqi Jiang , Zhipeng Li , Guowen Yuan , Laiying Zhang , Xu Hou . Liquid Gating Mechanism and Basic Properties Characterization: a New Experimental Design for Interface and Surface Properties in the Chemistry “101 Plan”. University Chemistry, 2024, 39(10): 113-120. doi: 10.12461/PKU.DXHX202407111
Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014
Yangrui Xu , Yewei Ren , Xinlin Liu , Hongping Li , Ziyang Lu . 具有高传质和亲和表面的NH2-UIO-66基疏水多孔液体用于增强CO2光还原. Acta Physico-Chimica Sinica, 2024, 40(11): 2403032-. doi: 10.3866/PKU.WHXB202403032
Yongmin Zhang , Shuang Guo , Mingyue Zhu , Menghui Liu , Sinong Li . Design and Improvement of Physicochemical Experiments Based on Problem-Oriented Learning: a Case Study of Liquid Surface Tension Measurement. University Chemistry, 2024, 39(2): 21-27. doi: 10.3866/PKU.DXHX202307026
Guoze Yan , Bin Zuo , Shaoqing Liu , Tao Wang , Ruoyu Wang , Jinyang Bao , Zhongzhou Zhao , Feifei Chu , Zhengtong Li , Yusuke Yamauchi , Saad Melhi , Xingtao Xu . Opportunities and Challenges of Capacitive Deionization for Uranium Extraction from Seawater. Acta Physico-Chimica Sinica, 2025, 41(4): 100032-. doi: 10.3866/PKU.WHXB202404006