Fluorination Reaction of P(Ⅲ) Compounds with the Electrophilic Fluorinating Reagent Selectfluor
- Corresponding author: Chen Qian, qianchen@gdut.edu.cn
Citation:
Huang Yulin, Chen Qian. Fluorination Reaction of P(Ⅲ) Compounds with the Electrophilic Fluorinating Reagent Selectfluor[J]. Chinese Journal of Organic Chemistry,
;2017, 37(10): 2745-2751.
doi:
10.6023/cjoc201704001
(a) Kosolapoff, G. M.; Maier, L. Organic Phosphorus Compounds, Wiley-Interscience, New York, 1972.
(b) Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415.(c) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
(d) Tang, Q.; Tu, A. P.; Deng, Z. Z.; Hu, M. Y.; Zhong, W. H. Chin. J. Org. Chem. 2013, 33, 954(in Chinese).
(a) Steininger, H.; Schuster, M.; Kreuer, K. D.; Kaltbeitzel, A.; Bingol, B.; Meyer, W. H.; Schauff, S.; Brunklaus, G.; Maier, J.; Spiess, H. W. Phys. Chem. Chem. Phys. 2007, 9, 1764.
(b) Spampinato, V.; Tuccitto, N.; Quici, S.; Calabrese, V.; Marletta, G.; Torrisi, A.; Licciardello, A. Langmuir 2010, 26, 8400.
(a) Shie, J.-J.; Fang, J.-M.; Wang, S.-Y.; Tsai, K.-C.; Cheng, Y.-S. E.; Yang, A.-S.; Hsiao, S.-C.; Su, C.-Y.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 11892.
(b) Shie, J.; Fang, J.; Wong, C. Angew. Chem. 2008, 120, 5872; Angew. Chem., Int. Ed. 2008, 47, 5788.
(c) Wydysh, E. A.; Medghalchi, S. M.; Vadlamudi, A.; Townsend, C. A. J. Med. Chem. 2009, 52, 3317.
(a) Pinault, N. Coord. Chem. Rev. 2003, 241, 1.
(b) Knappke, C. E. I.; von Wangelin, A. J. Chem. Soc. Rev. 2011, 40, 4948.
(c) Fernández-Pérez, H.; Etayo, P.; Panossian, A.; Vidal-Ferran, A. Chem. Rev. 2011, 111, 2119.
(a) Cho, C.-S.; Chen, L.-W.; Chiu, Y.-S. Polym. Bull. 1998, 41, 45.
(b) Cho, C.-S.; Fu, S.-C.; Chen, L.-W.; Wu, T.-R. Polym. Int. 1998, 47, 203.
(a) Engel, R. Chem. Rev. 1977, 77, 349.
(b) Camps, F.; Coll, J.; Fabrias, G.; Guerrero, A. Tetrahedron 1984, 40, 2871.
(c) Sikder, A. K.; Pandey, K. S.; Jaiswal, D. K.; Dube, S. N.; Kumar, D.; Husain, K.; Bhattacharya, R.; Das Gupta, S. J. Pharm. Pharmacol. 1992, 44, 1038.
(d) Sikder, A. K.; Ghosh, A. K.; Jaiswal, D. K. J. Pharm. Sci. 1993, 82, 258.(e) Eyer, P. Toxicol. Rev. 2003, 22, 165.
(f) Kim, T. H.; Oh, K. A.; Park, N. J.; Park, N. S.; Kim, Y. J.; Yum, E. K.; Jung, Y. S. J. Appl. Biomed. 2006, 4, 67.
(a) Michalski, J.; Lopusinski, A. Angew. Chem., Int. Ed. 1982, 21, 294.
(b) Dabkowski, W.; Michalski, J. J. Chem. Soc., Chem. Commun. 1987, 755.
(c) Lermontov, S. A.; Popov, A. V.; Zavorin, S. I.; Sukhojenko, I. I.; Kuryleva, N. V.; Martynov, I. V.; Zefirov, N. S.; Stang, P. J. Fluorine Chem. 1994, 66, 233.
(d) Farooq, O. J. Chem. Soc., Perkin Trans. 1 1998, 839.
(e) Wozniak, L. A.; Chworos, A.; Pyzowski, L. A. Tetrahedron Lett. 1999, 40, 9337.
(f) Gololobov, Y. G.; Krasnova, I. Y.; Matveeva, E. V.; Petrovskii, P. V. Russ. Chem. Bull., Int. Ed. 2010, 59, 1059.
(a) Kaushik, M. P.; Gupta, A. K.; Acharya, J.; Dubey, D. K. J. Fluorine Chem. 2008, 129, 226.
(b) Dubey, D. K.; Gupta, A. K.; Acharya, J.; Pardasani, D. Tetrahedron Lett. 2008, 49, 2232.
(c) Purohit, A. K.; Pardasani, D.; Kumar, A.; Goud, D. R.; Jain, R.; Dubey, D. K. Tetrahedron Lett. 2015, 56, 4593.
Liu, N.; Mao, L.-L.; Yang, B.; Yang, S.-D. Chem. Commun. 2014, 50, 10879.
doi: 10.1039/C4CC04830J
Chen, Q.; Zeng, J.; Yan, X.; Huang, Y.; Wen, C.; Liu, X.; Zhang, K. J. Org. Chem. 2016, 81, 10043.
doi: 10.1021/acs.joc.6b01932
Chen, Q.; Zeng, J.; Yan, X.; Huang, Y.; Du, Z.; Zhang, K.; Wen, C. Tetrahedron Lett. 2016, 57, 3379.
doi: 10.1016/j.tetlet.2016.06.078
Reddy, G. S.; Schmutzler, R. Z. Naturforsch. B 1970, 25, 1199.
Zhongyan Cao , Youzhi Xu , Menghua Li , Xiao Xiao , Xianqiang Kong , Deyun Qian . Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017
Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
Xudong Liu , Huili Fan , Junping Xiao , Min Yang , Yan Li . Teaching Approaches to the AE + AN Mechanism of Electrophilic Addition Reactions between Olefins and Inorganic Acids in Organic Chemistry. University Chemistry, 2025, 40(7): 367-372. doi: 10.12461/PKU.DXHX202409041
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
Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
Bo YANG , Gongxuan LÜ , Jiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346
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
Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
Hao Wu , Zhen Liu , Dachang Bai . 1H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
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
Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
Ying Xiong , Guangao Yu , Lin Wu , Qingwen Liu , Houjin Li , Shuanglian Cai , Zhanxiang Liu , Xingwen Sun , Yuan Zheng , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Specification Suggestions for Determination of Physical Constants of Organic Compounds. University Chemistry, 2025, 40(5): 106-121. doi: 10.12461/PKU.DXHX202503079
Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
Xueting Cao , Shuangshuang Cha , Ming Gong . 电催化反应中的界面双电层:理论、表征与应用. Acta Physico-Chimica Sinica, 2025, 41(5): 100041-. doi: 10.1016/j.actphy.2024.100041
Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
Zihao Guo , Shichen Ma , Kin Shing Chan . 烯烃环化反应中6电子试剂的等瓣相似性和等电子关系. University Chemistry, 2025, 40(6): 160-166. doi: 10.12461/PKU.DXHX202408038