Catalytic Intermolecular Direct Arylation of Perfluorobenzenes

Penta-, tetra-, tri-, and difluorobenzenes undergo direct arylation with a wide range of arylhalides in high yield. Inverse reactivity is observed compared to the common electrophilic aromatic substitution pathway since electron-deficient, C−H acidic arenes react preferentially. Computational studie...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2006-07, Vol.128 (27), p.8754-8756
Main Authors: Lafrance, Marc, Rowley, Christopher N, Woo, Tom K, Fagnou, Keith
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
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Summary:Penta-, tetra-, tri-, and difluorobenzenes undergo direct arylation with a wide range of arylhalides in high yield. Inverse reactivity is observed compared to the common electrophilic aromatic substitution pathway since electron-deficient, C−H acidic arenes react preferentially. Computational studies indicate that C−H bond cleavage occurs via a concerted carbon−palladium and carbon−hydrogen bond cleaving event involving a carbonate or a bromide ligand. The reactions are rapid, require only a slight excess of the perfluoroarene reagent, and utilize commercially available, air-stable catalyst precursors.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja062509l