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

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Title
Sequential C−H Borylation and N-Demethylation of 1,1′-Biphenylamines: Alternative Route to Polycyclic BN-Heteroarenes
Author(s)
Jianbo Zhang; Hoimin Jung; Dongwook Kim; Sehoon Park; Sukbok Chang
Publication Date
2019-05
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.58, no.22, pp.7361 - 7365
Publisher
WILEY-V C H VERLAG GMBH
Abstract
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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 PhSiH 3 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(C 6 F 5 ) 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 ⓒ 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
URI
https://pr.ibs.re.kr/handle/8788114/5980
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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