Synthesis and Characterization of a Neutral Tricoordinate Organoboron Isoelectronic with Amines

Amines and boranes are the archetypical Lewis bases and acids, respectively. The former can readily undergo one-electron oxidation to give radical cations, whereas the latter are easily reduced to afford radical anions. Here, we report the synthesis of a neutral tricoordinate boron derivative, which acts as a Lewis base and undergoes one-electron oxidation into the corresponding radical cation. These compounds can be regarded as the parent borylene (H-B:) and borinylium (H-B(+.)), respectively, stabilized by two cyclic (alkyl)(amino)carbenes. Ab initio calculations show that the highest occupied molecular orbital of the borane as well as the singly occupied molecular orbital of the radical cation are essentially a pair and a single electron, respectively, in the p(π) orbital of boron.