Direct Access to Ketones from Aldehydes via Rhodium-Catalyzed Cross-Coupling Reaction with Potassium Trifluoro(organo)borates

Direct Access to Ketones from Aldehydes via Rhodium-Catalyzed Cross-Coupling Reaction with Potassium Trifluoro(organo)borates

A direct cross-coupling reaction of aromatic aldehydes with potassium trifluoro(organo)borates afforded ketones in high yields and under mild conditions in the presence of a rhodium catalyst and acetone. This new reaction, involving a formal aldehyde C−H bond activation, is believed to proceed via a...

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Veröffentlicht in:Journal of the American Chemical Society 2004-12, Vol.126 (47), p.15356-15357
Hauptverfasser: Pucheault, Mathieu, Darses, Sylvain, Genet, Jean-Pierre
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
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Zusammenfassung:A direct cross-coupling reaction of aromatic aldehydes with potassium trifluoro(organo)borates afforded ketones in high yields and under mild conditions in the presence of a rhodium catalyst and acetone. This new reaction, involving a formal aldehyde C−H bond activation, is believed to proceed via a Heck-type mechanism followed by hydride transfer to acetone.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja044749b