Premium
Intramolecular Fluorocyclizations of Unsaturated Carboxylic Acids with a Stable Hypervalent Fluoroiodane Reagent
Author(s) -
Geary Gemma C.,
Hope Eric G.,
Stuart Alison M.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201507790
Subject(s) - reagent , hypervalent molecule , intramolecular force , chemistry , catalysis , fluoride , aryl , combinatorial chemistry , organic chemistry , inorganic chemistry , alkyl
Abstract 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 AgBF 4 . 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 18 F‐labelled radiotracers for PET imaging.