An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C−H Bond Activations
Bijoy P. Mathew, Hyun Ji Yang (Advisor: Sung You Hong, Jang-Ung Park)
Angewandte Chemie, 56(18), 5007-5011 (2017)

An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C−H Bond Activations

 

 

Abstract: 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 Pd2(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.