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 dibenzo[c,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. [ABSTRACT FROM AUTHOR]