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An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C−H Bond Activations
Author(s) -
Mathew Bijoy P.,
Yang Hyun Ji,
Kim Joohee,
Lee Jae Bin,
Kim YunTae,
Lee Sungmin,
Lee Chang Young,
Choe Wonyoung,
Myung Kyungjae,
Park JangUng,
Hong Sung You
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201700405
Subject(s) - triphenylene , tandem , intramolecular force , chemistry , catalysis , aryl , combinatorial chemistry , selectivity , catalytic cycle , molecule , stereochemistry , organic chemistry , materials science , alkyl , composite material
C−H activation is a versatile tool for appending aryl groups to aromatic systems. However, heavy demands on multiple catalytic cycle operations and site‐selectivity have limited its use for graphene segment synthesis. A Pd‐catal‐ yzed one‐step synthesis of functionalized triphenylene frameworks is disclosed, which proceeds by 2‐ or 4‐fold C−H arylation of unactivated benzene derivatives. A Pd 2 (dibenzylideneacetone) 3 catalytic system, using cyclic diaryliodonium salts as π‐extending agents, leads to site‐selective inter‐ and intramolecular tandem arylation sequences. Moreover, N ‐substituted triphenylenes are applied to a field‐effect transistor sensor for rapid, sensitive, and reversible alcohol vapor detection.