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

Jianbo Zhang, Hoimin Jung, Dongwook Kim, Sehoon Park*, Sukbok Chang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)7361-7365
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number22
DOIs
StatePublished - 27 May 2019
Externally publishedYes

Keywords

  • boranes
  • C−H activation
  • heterocycles
  • isosterers
  • reaction mechanisms

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