Synthesis, Structure, and Reactivity of Acid-Free Neutral Oxoborane

An efficient synthesis of an acid-free neutral oxoborane of the type carboranyl-B(carbene)=O has been developed via a serendipitous discovery from the reaction of 1,2-[BBr(carbene)]-o-carborane with AgOTf. This represents a new type of oxoborane. The stabilization of this oxoborane may be attributed to 1) kinetic stabilization provided by a bulky 3D carboranyl ligand and 2) thermodynamic stabilization offered by a carbene ligand. Crystallographic analyses support the presence of the shortest terminal B=O double bond ever reported thus far. Its reactivity has also been examined.