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

• Published in: Angewandte Chemie Vol. 127; no. 49; pp. 15124 - 15127
• Main Authors: Geary, Gemma C., Hope, Eric G., Stuart, Alison M.
• Format: Journal Article
• Language: English
• 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
• ISSN: 0044-8249; 1521-3757
• DOI: 10.1002/ange.201507790

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.