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A dichotomy in the reactivity of B–H bonds is reported. A bis(N-heterocyclic carbene)-ligated iridium(III) complex can effect rapid deuteration of boronate esters at room temperature with low catalyst loadings; however, borane and 9-BBN both undergo deuteration in the absence of catalyst, and do not react with the iridium complexes. This is proposed to result from the inductive electron-withdrawing properties of the boronic ester substituents. Deuterated boronic esters can be accessed rapidly at room temperature with only very low loadings of iridium catalyst.
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