Details

Autor(en) / Beteiligte

• Zhang, Qing-Wei
• Brusoe, Andrew T.
• Mascitti, Vincent
• Hesp, Kevin D.
• Blakemore, David C.
• Kohrt, Jeffrey T.
• Hartwig, John F.

Titel

Fluorodecarboxylation for the Synthesis of Trifluoromethyl Aryl Ethers

Ist Teil von

• Angewandte Chemie (International ed.), 2016-08, Vol.55 (33), p.9758-9762

Auflage

International ed. in English

Ort / Verlag

Germany: Blackwell Publishing Ltd

Erscheinungsjahr

2016

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• The synthesis of mono‐, di‐, and trifluoromethyl aryl ethers by fluorodecarboxylation of the corresponding carboxylic acids is reported. AgF2 induces decarboxylation of aryloxydifluoroacetic acids, and AgF, either generated in situ or added separately, serves as a source of fluorine to generate the fluorodecarboxylation products. The addition of 2,6‐difluoropyridine increased the reactivity of AgF2, thereby increasing the range of functional groups and electronic properties of the aryl groups that are tolerated. The reaction conditions used for the formation of trifluoromethyl aryl ethers also served to form difluoromethyl and monofluoromethyl aryl ethers. Radical F: AgF2 induces fluorodecarboxylation of phenoxy difluoroacetic acids to afford trifluoromethyl aryl ethers. Pyridine additives modulate the reactivity of AgF2, and enable the reaction to proceed with a variety of substrates.