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Reaction of 2,6-dimesityl pyridine (Lpy) with BBr3 leads to the spontaneous formation of the trigonal dibromoborenium cation [Lpy·BBr2]+viabromide ejection. Systematic structural and computational studies, and the reactivity displayed by a closely related N-heterocyclic carbene (NHC) donor, reveal the role played by arene–borane interactions in this chemistry. [Lpy·BBr2]+ features a structurally characterized (albeit weak) electrostatic interaction between the borane Lewis acid and flanking arene π systems.
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