Intramolecular Fluorocyclizations of Unsaturated Carboxylic Acids with a Stable Hypervalent Fluoroiodane Reagent

A new class of fluorinated lactones was prepared by the intramolecular fluorocyclizations of unsaturated carboxylic acids by using the stable fluoroiodane reagent in combination with AgBF4. This unique reaction incorporates a cyclization, an aryl migration, and a fluorination all in one step. The fl...

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Published inAngewandte Chemie Vol. 127; no. 49; pp. 15124 - 15127
Main Authors Geary, Gemma C., Hope, Eric G., Stuart, Alison M.
Format Journal Article
LanguageEnglish
German
Published Weinheim WILEY-VCH Verlag 01.12.2015
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects
Acids
Aromatic compounds
Carboxylic acids
Catalysts
Chemistry
Cyclisierungen
Fluor
Fluorides
Fluorination
Hypervalente Verbindungen
Lactone
Lactones
Migration
Positron emission
Radioactive tracers
Reagents
Silber
Tomography
Unsaturated
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Summary:A new class of fluorinated lactones was prepared by the intramolecular fluorocyclizations of unsaturated carboxylic acids by using the stable fluoroiodane reagent in combination with AgBF4. This unique reaction incorporates a cyclization, an aryl migration, and a fluorination all in one step. The fluoroiodane reagent, prepared easily from fluoride, can also be used without a metal catalyst to give moderate yields within just 1 hour, thus demonstrating that it is a suitable reagent for developing new 18F‐labelled radiotracers for PET imaging. Alles in einem: Eine neue Klasse von Lactonen mit tertiärer Alkylfluoridgruppe wurde mithilfe eines stabilen Fluoriodanreagens in hohen Ausbeuten hergestellt. Diese einzigartige Reaktion umfasst eine Cyclisierung, eine Aryl‐Wanderung und eine Fluorierung in einem einzigen Schritt.
Bibliography:istex:8B3651A10425B4D66E9BF14C48DB525EA56C974A
ark:/67375/WNG-413BJCND-M
ArticleID:ANGE201507790
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201507790