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Collect. Czech. Chem. Commun. 2002, 67, 1285-1295
https://doi.org/10.1135/cccc20021285

Radical Reaction Using an Organocopper Reagent Derived from Ethyl Bromodifluoroacetate

Kazuyuki Sato, Yuko Ogawa, Misato Tamura, Mika Harada, Terumasa Ohara, Masaaki Omote, Akira Ando and Itsumaro Kumadaki*

Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan

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  • Xi Chanjuan, Chen Shenhao, Zou Song, Chen Chao: Photoredox-Catalyzed 2:2 Coupling of Aryl Ethylene and Brcf2co2me: A Facile Synthesis of Two Difluoroacetylated Hexestrol Derivatives. SSRN Journal 2022. <https://doi.org/10.2139/ssrn.4193557>
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  • Kostromitin Vladislav S., Zemtsov Artem A., Kokorekin Vladimir A., Levin Vitalij V., Dilman Alexander D.: Atom-transfer radical addition of fluoroalkyl bromides to alkenes via a photoredox/copper catalytic system. Chem. Commun. 2021, 57, 5219. <https://doi.org/10.1039/D1CC01609A>
  • Peng Deqian, Fan Wu, Zhao Xueqi, Chen Wei, Wen Yuan, Zhang Li, Li Suhua: Zinc–Brønsted acid mediated practical hydrotrifluoromethylation of alkenes with CF3Br. Org. Chem. Front. 2021, 8, 6356. <https://doi.org/10.1039/D1QO01073E>
  • Luo Xuewei, Fan Zhengning, Zhang Bo, Chen Chao, Xi Chanjuan: Visible-light-triggered direct keto-difluoroacetylation of styrenes with (fluorosulfonyl)difluoroacetate and dimethyl sulfoxide leads to α-difluoroacetylated ketones. Chem. Commun. 2019, 55, 10980. <https://doi.org/10.1039/C9CC06037E>
  • Yu Wei, Ouyang Yao, Xu Xiu‐Hua, Qing Feng‐Ling: Visible Light‐Induced Methoxycarbonyldifluoromethylation of Trimethylsilyl Enol Ethers and Allyltrimethylsilanes with FSO2CF2CO2Me. Chin. J. Chem. 2018, 36, 1024. <https://doi.org/10.1002/cjoc.201800318>
  • Li Dengke, Mao Tingting, Huang Jinbo, Zhu Qiang: Copper-Catalyzed Bromodifluoroacetylation of Alkenes with Ethyl Bromodifluoroacetate. J. Org. Chem. 2018, 83, 10445. <https://doi.org/10.1021/acs.joc.8b01434>
  • Xu Lei, Zhang Qi, Xie Qiang, Huang Bei, Dai Jian-Jun, Xu Jun, Xu Hua-Jian: Pd-catalyzed defluorination/arylation of α-trifluoromethyl ketones via consecutive β-F elimination and C–F bond activation. Chem. Commun. 2018, 54, 4406. <https://doi.org/10.1039/C8CC01568F>
  • Wu Ye-bin, Lu Guo-ping, Yuan Tao, Xu Zhu-bing, Wan Li, Cai Chun: Oxidative trifluoromethylation and fluoroolefination of unactivated olefins. Chem. Commun. 2016, 52, 13668. <https://doi.org/10.1039/C6CC08178A>
  • Ma Guobin, Wan Wen, Li Jialiang, Hu Qingyang, Jiang Haizhen, Zhu Shizheng, Wang Jing, Hao Jian: An efficient regioselective hydrodifluoromethylation of unactivated alkenes with TMSCF2CO2Et at ambient temperature. Chem. Commun. 2014, 50, 9749. <https://doi.org/10.1039/C4CC04591B>
  • Yamada Shigeyuki, Kato Masahiro, Komori Yudai, Konno Tsutomu, Ishihara Takashi: Easy access to CF2-containing molecules based on the reaction of 2,2,3,3-tetrafluorooxetane with various nucleophiles. Biomol Chem 2011, 9, 5493. <https://doi.org/10.1039/c1ob05545c>
  • Sato Kazuyuki, Ishida Yoshitaka, Murata Eriko, Oida Yumiko, Mori Yasumitsu, Okawa Miho, Iwase Kayoko, Tarui Atsushi, Omote Masaaki, Kumadaki Itsumaro, Ando Akira: Rh-catalyzed novel α-fluoroalkylation of α,β-unsaturated ketones and its mechanism. Tetrahedron 2007, 63, 12735. <https://doi.org/10.1016/j.tet.2007.09.081>
  • Percec Virgil, Guliashvili Tamaz, Ladislaw Janine S., Wistrand Anna, Stjerndahl Anna, Sienkowska Monika J., Monteiro Michael J., Sahoo Sangrama: Ultrafast Synthesis of Ultrahigh Molar Mass Polymers by Metal-Catalyzed Living Radical Polymerization of Acrylates, Methacrylates, and Vinyl Chloride Mediated by SET at 25 °C. J. Am. Chem. Soc. 2006, 128, 14156. <https://doi.org/10.1021/ja065484z>
  • KUMADAKI Itsumaro: Synthesis of Fluorine Compounds Based on Special Property of Fluorine Compounds. YAKUGAKU ZASSHI 2006, 126, 1059. <https://doi.org/10.1248/yakushi.126.1059>
  • Sato K., Omote M., Ando A., Kumadaki I.: Reactions of ethyl bromodifluoroacetate in the presence of copper powder. J FLUORINE CHEM 2004, 125, 509. <https://doi.org/10.1016/j.jfluchem.2003.11.023>
  • Okano Takashi, Chokai Masayuki, Hiraishi Makiko, Yoshizawa Michito, Kusukawa Takahiro, Fujita Makoto: Phenyl trifluorovinyl sulfide: a radical acceptor for preparation of gem-difluoromethylene compounds. Tetrahedron 2004, 60, 4031. <https://doi.org/10.1016/j.tet.2004.03.020>
  • Sato Kazuyuki, Ogawa Yuko, Tamura Misato, Harada Mika, Ohara Terumasa, Omote Masaaki, Ando Akira, Kumadaki Itsumaro: Radical Reaction Using an Organocopper Reagent Derived from Ethyl Bromodifluoroacetate. ChemInform 2003, 34. <https://doi.org/10.1002/chin.200313064>
  • Sato Kazuyuki, Nakazato Sumika, Enko Hiroko, Tsujita Hiroaki, Fujita Katsumi, Yamamoto Takeya, Omote Masaaki, Ando Akira, Kumadaki Itsumaro: 1,4-Addition reaction of ethyl bromodifluoroacetate to Michael acceptors in the presence of copper powder. J FLUORINE CHEM 2003, 121, 105. <https://doi.org/10.1016/S0022-1139(03)00003-4>
  • Hagooly Aviv, Sasson Revital, Rozen Shlomo: A Novel Method for the Preparation of α,α‘-Difluoroesters and Acids Using BrF3. J. Org. Chem. 2003, 68, 8287. <https://doi.org/10.1021/jo034829i>