Synthesis of Polyfluoroalkyl Aza-Polycyclic Aromatic Hydrocarbons Enabled by Addition of Perfluoroalkyl Radicals onto Vinyl Azides

被引：86
作者：
Wang, Yi-Feng [1 ]
Lonca, Geoffroy Herve [1 ]
Le Runigo, Maiwenn [1 ]
Chiba, Shunsuke [1 ]
机构：
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 16期
关键词：
DIVERGENT SYNTHESIS; BOND FORMATION; TRIFLUOROMETHYLATION; CYCLOPROPANOLS; ARYL; 6-(TRIFLUOROMETHYL)PHENANTHRIDINES; TRIFLUOROETHYLATION; HETEROARENES; NITROGEN; CF3SIME3;
D O I：
10.1021/ol501997n
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Radical perfluoroalkylation of alpha-(biaryl-2-yl)vinyl azides is capable of supplying polyfluoroalkyl aza-polycyclic aromatic hydrocarbons (aza-PAHs). Commercially available Me3SiRf (R-f = 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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收藏
页码：4272 / 4275
页数：4
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