24005-42-3Relevant academic research and scientific papers
Sequential C?H Borylation and N-Demethylation of 1,1′-Biphenylamines: Alternative Route to Polycyclic BN-Heteroarenes
Zhang, Jianbo,Jung, Hoimin,Kim, Dongwook,Park, Sehoon,Chang, Sukbok
, p. 7361 - 7365 (2019)
Described herein is an unprecedented access to BN-polyaromatic compounds from 1,1′-biphenylamines by sequential borane-mediated C(sp2)?H borylation and intramolecular N-demethylation. The conveniently in situ generated Piers’ borane from a borinic acid reacts with a series of N,N-dimethyl-1,1′-biphenyl-2-amines in the presence of PhSiH3 to afford six-membered amine-borane adducts bearing a C(sp2)?B bond at the C2′-position. These species undergo an intramolecular N-demethylation with a B(C6F5)3 catalyst to provide BN-isosteres of polyaromatics. According to computational studies, a stepwise ionic pathway is suggested. Photophysical characters of the resultant BN-heteroarenes shown them to be distinctive from those of all-carbon analogues.
