Boron Centres Allow Design, Control and Systematic Tuning of Neutral Homoaromatics for Functionalization Purposes.

Homoaromatic compounds are currently viewed mainly as an interesting novelty with little to no practical application. Based on calculations within density functional theory, we show that the unique charge redirection properties of tricoordinate boron, along with it being isolobal to a carbocation, allow for a larger range of two-electron donors to be utilized, leading to the rational design of homoaromatic compounds better suited to functionalization. Among others, these compounds show a strong dependency on the relative positioning of the hetero-atoms within the ring system, a modulation control rendered possible by the insertion of the boron centres.