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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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

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spelling	sg-ntu-dr.10356-1037382023-02-28T19:32:52Z Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides Wang, Yi-Feng Lonca, Geoffroy Hervé Le Runigo, Maïwenn Chiba, Shunsuke School of Physical and Mathematical Sciences Ecole Polytechnique University of Strasbroug DRNTU::Science::Chemistry::Organic chemistry 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. MOE (Min. of Education, S’pore) Accepted version 2014-12-26T07:25:34Z 2019-12-06T21:19:11Z 2014-12-26T07:25:34Z 2019-12-06T21:19:11Z 2014 2014 Journal Article 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. https://hdl.handle.net/10356/103738 http://hdl.handle.net/10220/24553 10.1021/ol501997n en Organic letters © 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]. 4 p. application/pdf
institution	Nanyang Technological University
building	NTU Library
continent	Asia
country	Singapore Singapore
content_provider	NTU Library
collection	DR-NTU
language	English
topic	DRNTU::Science::Chemistry::Organic chemistry
spellingShingle	DRNTU::Science::Chemistry::Organic chemistry Wang, Yi-Feng Lonca, Geoffroy Hervé Le Runigo, Maïwenn Chiba, Shunsuke Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides
description	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.
author2	School of Physical and Mathematical Sciences
author_facet	School of Physical and Mathematical Sciences Wang, Yi-Feng Lonca, Geoffroy Hervé Le Runigo, Maïwenn Chiba, Shunsuke
format	Article
author	Wang, Yi-Feng Lonca, Geoffroy Hervé Le Runigo, Maïwenn Chiba, Shunsuke
author_sort	Wang, Yi-Feng
title	Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides
title_short	Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides
title_full	Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides
title_fullStr	Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides
title_full_unstemmed	Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides
title_sort	synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides
publishDate	2014
url	https://hdl.handle.net/10356/103738 http://hdl.handle.net/10220/24553
_version_	1759854918058901504

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

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