Diversity-Oriented Approach to CF<sub>3</sub>CHF-, CF<sub>3</sub>CFBr-, CF<sub>3</sub>CF<sub>2</sub>-, (CF<sub>3</sub>)<sub>2</sub>CH-, and CF<sub>3</sub>(SCF<sub>3</sub>)CH-Substituted Arenes from 1-(Diazo-2,2,2-trifluoroethyl)arenes
作者:Enrico Emer、Jack Twilton、Matthew Tredwell、Samuel Calderwood、Thomas Lee Collier、Benoît Liégault、Marc Taillefer、Véronique Gouverneur
DOI:10.1021/ol5030184
日期:2014.11.21
Arenes substituted with perfluoroalkyl groups are attractive targets for drug and agrochemical development. Exploiting the carbenic character of donor/acceptor diazo compounds, a diversity-oriented synthesis of perfluoroalkylated arenes, for late stage fluorofunctionalization, is described. The reaction of 1-(diazo-2,2,2-trifluoroethyl)arenes with HF, F/Br, F-2, CF3H, and CF3SH sources give direct access to a variety of perfluoroalkyl-substituted arenes presenting with incremental fluorine content. The value of this approach is also demonstrated for radiochemistry and positron emission tomography with the [F-18]-labeling of CF3CHF-, CF3CBrF-, and CF3CF2-arenes from [F-18]fluoride.