Silver-Catalyzed Ring-Opening Strategy for the Synthesis of β- and γ‑Fluorinated Ketones

A regioselective synthesis of β- and γ-fluorinated ketones via silver-catalyzed ring opening is described. A variety of β- and γ-fluorinated ketones are efficiently prepared, respectively, from tertiary cyclopropanol and cyclobutanol precursors, providing a straightforward approach for the introduct...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 137; no. 10; pp. 3490 - 3493
Main Authors Zhao, Huijun, Fan, Xuefeng, Yu, Jiajia, Zhu, Chen
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.03.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
MEDICINAL CHEMISTRY
COPPER-MEDIATED FLUORINATION
BENZYLIC FLUORINATION
C-H FLUORINATION
ENANTIOSELECTIVE FLUORINATION
LATE-STAGE
PHASE-TRANSFER CATALYST
BOND FORMATION
ARYL FLUORIDES
UNACTIVATED ALKENES
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Summary:A regioselective synthesis of β- and γ-fluorinated ketones via silver-catalyzed ring opening is described. A variety of β- and γ-fluorinated ketones are efficiently prepared, respectively, from tertiary cyclopropanol and cyclobutanol precursors, providing a straightforward approach for the introduction of a fluorine atom into complex molecules. Preliminary mechanistic studies suggest that a radical-mediated sequential C–C bond cleavage and C–F bond formation pathway is involved.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b00939