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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]