Cross-Coupling of Cyclopropyl- and Cyclobutyltrifluoroborates with Aryl and Heteroaryl Chlorides

Cross-Coupling of Cyclopropyl- and Cyclobutyltrifluoroborates with Aryl and Heteroaryl Chlorides

Suitable conditions were found for the Suzuki−Miyaura cross-coupling reaction of potassium cyclopropyl- and cyclobutyltrifluoroborates with aryl chlorides. Both of these secondary alkyl trifluoroborates coupled in moderate to excellent yield with electron-rich, electron-poor, and hindered aryl chlor...

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Veröffentlicht in:Journal of organic chemistry 2008-10, Vol.73 (19), p.7481-7485
Hauptverfasser: Molander, Gary A, Gormisky, Paul E
Format: Artikel
Sprache:eng
Schlagworte:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Benzene Derivatives - chemical synthesis
Borates - chemistry
Chemistry
Cyclobutanes - chemistry
Cyclopropanes - chemistry
Exact sciences and technology
Fluorides - chemistry
Hydrocarbons, Chlorinated - chemistry
Organic chemistry
Preparations and properties
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Zusammenfassung:Suitable conditions were found for the Suzuki−Miyaura cross-coupling reaction of potassium cyclopropyl- and cyclobutyltrifluoroborates with aryl chlorides. Both of these secondary alkyl trifluoroborates coupled in moderate to excellent yield with electron-rich, electron-poor, and hindered aryl chlorides to give a variety of substituted aryl cyclopropanes and cyclobutanes.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo801269m