Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/103738
Title: Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides
Authors: Wang, Yi-Feng
Lonca, Geoffroy Hervé
Le Runigo, Maïwenn
Chiba, Shunsuke
Keywords: DRNTU::Science::Chemistry::Organic chemistry
Issue Date: 2014
Source: Wang, Y.-F., Lonca, G. H., Le Runigo, M., & Chiba, S. (2014). Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides. Organic letters, 16(16), 4272-4275.
Series/Report no.: Organic letters
Abstract: Radical perfluoroalkylation of α-(biaryl-2-yl)vinyl azides is capable of supplying polyfluoroalkyl aza-polycyclic aromatic hydrocarbons (aza-PAHs). Commercially available Me3SiRf (Rf = CF3, C2F5, and C3F7) are employed as the sources of perfluoroalkyl radicals upon oxidation with PhI(OAc)2. The addition of perfluoroalkyl radicals to biarylvinyl azides generates the corresponding iminyl radicals, which subsequently cyclize with the intramolecular arene moiety, furnishing aza-PAH skeletons having polyfluoroalkyl (RfCH2) function.
URI: https://hdl.handle.net/10356/103738
http://hdl.handle.net/10220/24553
DOI: http://dx.doi.org/10.1021/ol501997n
Rights: © 2014 American Chemical Society. This is the author created version of a work that has been peer reviewed and accepted for publication by Organic Letters, American Chemical Society. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1021/ol501997n].
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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