Solution Phase Reactivity of Dibenzo[c,e][1,2]azaborinine: Activation and Insertion into Si‐E Single Bonds (E=H, OSi(CH<sub>3</sub>)<sub>3</sub>, F, Cl) by a BN‐Aryne
Constanze Keck, Jennifer Hahn, Divanshu Gupta, Holger F. Bettinger
Abstract
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.
Topics & Concepts
BoronAryneChemistryReactivity (psychology)NitrogenSiliconCrystallographyStereochemistryMedicinal chemistryComputational chemistryOrganic chemistryMedicinePathologyAlternative medicineCyclization and Aryne ChemistrySynthesis and Properties of Aromatic CompoundsSynthesis and characterization of novel inorganic/organometallic compounds