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

Emer, E, Twilton, J, Tredwell, M, Calderwood, S, Collier, T L, Liegault, B, Taillefer, M and Gouverneur, V 2014. Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(diazo-2,2,2-trifluoroethyl)arenes. Organic Letters 16 (22) , pp. 6004-6007. 10.1021/ol5030184

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Abstract

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.

Item Type: Article
Status: Published
Schools: Medicine
Publisher: American Chemical Society
ISSN: 1523-7060
Last Modified: 11 Jun 2019 14:00
URI: http://orca.cf.ac.uk/id/eprint/122218

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