Solution Phase Reactivity of Dibenzo[c,e][1,2]azaborinine: Activation and Insertion into Si-E Single Bonds (E=H,OSi(CH3)3, F,Cl) by a BN-Aryne

The boron-nitrogen analogue of ortho-benzyne, 1,2-azaborinine, is a reactive intermediate that features a formal boron-nitrogen triple bond. We here show by combining experimental and computational techniques that the Lewis acidity of the boron center of dibenzoc,e]1,2]azaborinine allows interaction with the silicon containing single bonds Si?E through the silicon bonding partner E (E=F, Cl, OR, H). The binding to boron activates the Si?E bonds for subsequent insertion reaction. This shows that the BN-aryne is a ferocious species that even can activate and insert into the very strong Si?F bond.