Sequential C-H Borylation and N-Demethylation of 1,1 '-Biphenylamines: Alternative Route to Polycyclic BN-Heteroarenes

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Described herein is an unprecedented access to BN-polyaromatic compounds from 1,1 ' -biphenylamines by sequential borane-mediated C(sp(2))-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(sp(2))-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.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2019-05
Language
English
Article Type
Article
Citation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.58, no.22, pp.7361 - 7365

ISSN
1433-7851
DOI
10.1002/anie.201902499
URI
http://hdl.handle.net/10203/264013
Appears in Collection
CH-Journal Papers(저널논문)
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