Incorporation of HO and CO into a BN-embedded 3-3-acephenanthrylene derivative.

A fused tetracyclic BN-species 1 featuring nucleophilic nitrogen and electrophilic boron centers behaves as a reactive N/B frustrated Lewis pair (FLP) for small molecule activation. Specifically, the O-H and C[double bond, length as m-dash]O bonds have been cleaved by 1 with the formation of fused borinic acid 2, borenium species 3, anionic boranuidacarboxylic acid 4 and oxadiazaborolidinone 5, respectively. Quantum-mechanical calculations are conducted to comprehensively understand the activation processes of small molecules by 1.