Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides

Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides

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 addi...

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Bibliographic Details
Main Authors: Wang, Yi-Feng, Lonca, Geoffroy Hervé, Le Runigo, Maïwenn, Chiba, Shunsuke
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
Subjects:
DRNTU::Science::Chemistry::Organic chemistry
Online Access:https://hdl.handle.net/10356/103738
http://hdl.handle.net/10220/24553
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Institution: Nanyang Technological University
Language: English
Description
Summary: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.

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