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Fluorination of Aryl Boronic Acids Using Acetyl Hypofluorite Made Directly from Diluted Fluorine

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journal contribution
posted on 06.12.2013, 00:00 by Inna Vints, Julia Gatenyo, Shlomo Rozen
Aryl boronic acids or pinacol esters containing EDG were converted in good yields and fast reactions to the corresponding aryl fluorides using the readily obtainable solutions of AcOF. In reactions with aryl boronic acids containing EWG at the para position, there are two competing forces: one directing the fluorination to take place ortho to the boronic acid and the other, toward an ipso substitution. With EWG meta to the boronic acid, substitution ipso to the boron moiety takes place in good yields.