Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(diazo-2,2,2-trifluoroethyl)arenes.

Journal article

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.

Authors: Emer, E; Twilton, J; Tredwell, M; Calderwood, S; Collier, T

• Publication status: Published
• Publisher: American Chemical Society
• Journal: Organic letters
• Volume: 16
• Issue: 22
• Pages: 6004-6007
• Publication date: 2014-11-01
• DOI: 10.1021/ol5030184
• EISSN: 1523-7052
• ISSN: 1523-7060
• Language: English