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...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2014
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| Online Access: | https://hdl.handle.net/10356/103738 http://hdl.handle.net/10220/24553 |
| _version_ | 1826118145932263424 |
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| author | Wang, Yi-Feng Lonca, Geoffroy Hervé Le Runigo, Maïwenn Chiba, Shunsuke |
| 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 |
| author_sort | Wang, Yi-Feng |
| collection | NTU |
| 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. |
| first_indexed | 2024-10-01T04:38:56Z |
| format | Journal Article |
| id | ntu-10356/103738 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:38:56Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-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 |
| 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 |
| title | 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_short | 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 |
| topic | DRNTU::Science::Chemistry::Organic chemistry |
| url | https://hdl.handle.net/10356/103738 http://hdl.handle.net/10220/24553 |
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