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Simple synthesis of heavy oxygen-labelled alcohols

27-May-2013

Research reports 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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