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

• Published in: Angewandte Chemie International Edition Vol. 54; no. 49; pp. 14911 - 14914
• 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; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Acids; Carboxylic acids; Catalysts; Chemistry; Chemistry, Multidisciplinary; cyclizations; Fluorides; Fluorination; fluorine; hypervalent compounds; Lactones; Physical Sciences; Positron emission; Radioactive tracers; Reagents; Science & Technology; silver; Tomography; CATALYZED FLUORINATION; hypervalent compounds; 1,3-DICARBONYL COMPOUNDS; ELECTROPHILIC FLUOROCYCLIZATION; FLUOROLACTONIZATION; cyclizations; ALCOHOLS; MILD; lactones; AMINOFLUORINATION; ESTERS; F-TEDA-BF4; silver; LACTONIZATION; fluorine
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.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. All in one: A new class of lactones containing a tertiary alkyl fluoride was prepared in high yields by using a stable fluoroiodane reagent. This unique reaction incorporates a cyclization, an aryl migration, and a fluorination all in one step.