Rozen and co-workers report a novel and extremely simple method for synthesising 18O-labelled alcohols using commercial boronic acids and a reagent prepared from elemental fluorine.
Alcohols labelled with 18O are very valuable as biological probes for a variety of studies which are often limited by the availability of labelled precursors for use in the synthesis of the compounds of interest.
Scientists in Israel prepared an 18O-labelled acetonitrile complex of hypofluorous acid by simply bubbling dilute F2 through acetonitrile and 18O-labelled water. They performed a series of reactions of this complex with a variety of aliphatic and aromatic boronic acids at room temperature to produce a series of 18O-labelled alcohols within just a few minutes and in excellent yields – generally upwards of 90 per cent.
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The first general route for efficient synthesis of 18O labelled alcohols using the HOF⋅CH3CN complex
Shlomo Rozen, Julia Luria and Inna Vints
Chem. Commun., 2013, Accepted Manuscript
DOI: 10.1039/C3CC42337A
