Deuteration of boranes : catalysed versus non-catalysed processes

Nelson, David J. and Egbert, Jonathan D. and Nolan, Steven P. (2013) Deuteration of boranes : catalysed versus non-catalysed processes. Dalton Transactions, 42 (12). pp. 4105-4109. ISSN 1477-9234

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Abstract

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.