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Visible-Light Induced Radical Perfluoroalkylation/Cyclization Strategy To Access 2‑Perfluoroalkylbenzothiazoles/Benzoselenazoles by EDA Complex

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journal contribution
posted on 17.05.2019, 15:52 by Yan Liu, Xiao-Lan Chen, Kai Sun, Xiao-Yun Li, Fan-Lin Zeng, Xiao-Ceng Liu, Ling-Bo Qu, Yu-Fen Zhao, Bing Yu
A novel and practical fluoroalkyl radical-initiated cascade reaction was developed to access diverse 2-fluoroalkylbenzothiazoles by reacting various fluoroalkyl radical sources, including perfluoroalkyl iodide (ICnF2n+1, n = 3–8, 10), ICF­(CF3)2, ICF2COOEt, ICF2CF2Cl, or ICF2CF2Br, tetramethylethane-1,2-diamine (TMEDA), and 2-isocyanoaryl thioethers in tetrahydrofuran under nitrogen atmosphere and blue-light irradiation conditions. Furthermore, this one-pot protocol could well be expanded to access various 2-fluoroalkylbenzoselenazoles starting from (2-isocyanophenyl)­(methyl)­selane, perfluoroalkyl iodides (ICnF2n+1, n = 3–8) or ICF2COOEt and TMEDA.