Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 18, Pages 5007-5011Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700405
Keywords
arylation; C-H activation; diaryliodonium salt; palladium; triphenylene
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Funding
- National Research Foundation of Korea [NRF-2016R1A2B4015497]
- IT RAMP
- D program of MOTIE/KEIT [10046306]
- IBS fellowship [IBS-R022-D1-2017]
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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-catalyzed 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 pi-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.
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