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

Author:
Liu, Yan, Chen, Xiao-Lan, Sun, Kai, Li, Xiao-Yun, Zeng, Fan-Lin, Liu, Xiao-Ceng, Qu, Ling-Bo, Zhao, Yu-Fen, Yu, Bing
Source:
Organic letters 2019 v.21 no.11 pp. 4019-4024
ISSN:
1523-7052
Subject:
blue light, chemical reactions, chemical structure, irradiation, nitrogen, organoiodine compounds, perfluorocarbons, tetrahydrofuran
Abstract:
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.
Agid:
6464101