The reduction of an N‐heterocyclic carbene (1,3‐diisopropyl‐4,5‐dimethylimidazolin‐2‐ylidene, IiPrMe2
) adduct of dichloro(ortho‐bromophenyl)borane by tert‐butyl lithium at low temperature yields the IiPrMe2
adduct A of parent benzoborirene, a highly strained boron‐containing bicyclic compound. A is unstable at room temperature and dimerizes at low temperature to the bis‐IiPrMe2
adduct of 9,10‐dihydro‐9,10‐diboraanthracene, characterized by single‐crystal X‐ray crystallography.
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 SiÀ E through the silicon bonding partner E (E = F, Cl, OR, H). The binding to boron activates the SiÀ 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 SiÀ F bond.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.