Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(diazo-2,2,2-trifluoroethyl)arenes.
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, F2, 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 [(18)F]-labeling of CF3CHF-, CF3CBrF-, and CF3CF2-arenes from [(18)F]fluoride.
Chemistry Research Laboratory, University of Oxford , 12 Mansfield Road, OX1 3TA Oxford, U.K.
Enrico
E
Emer
Jack
J
Twilton
Matthew
M
Tredwell
Samuel
S
Calderwood
Thomas Lee
TL
Collier
Benoît
B
Liégault
Marc
M
Taillefer
Véronique
V
Gouverneur
D001391:Azo Compounds / Q000737:chemistry*; D005462:Fluorine Radioisotopes / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D049268:Positron-Emission Tomography
D001391:Azo Compounds; D005462:Fluorine Radioisotopes; D006842:Hydrocarbons, Brominated; D006845:Hydrocarbons, Fluorinated