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Abstract
Selective incorporation of deuterium atoms into molecules is of high interest for
labeling purposes and for optimizing properties of drug candidates. A mild and environmentally
benign method for the deuteration of alkyl iodides via radical pathway using D2O as
source of deuterium has been developed. The reaction is initiated and mediated by
triethylborane in the presence of dodecanethiol as a catalyst. This method is compatible
with a wide range of functional groups and provides the monodeuterated products in
good yields and with a high level of deuterium incorporation. It opens promising opportunities
for the development of enantioselective radical reactions. Moreover, a revision of
the mechanism of the deoxygenation reaction of xanthates using R3B and water (Wood
deoxygenation) is presented.