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

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Angewandte Chemie (International ed. in English), ISSN: 1521-3773, Vol: 56, Issue: 18, Page: 5007-5011

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Mathew, Bijoy P.; Yang, Hyun Ji; Kim, Joohee; Lee, Jae Bin; Kim, Yun-Tae; Lee, Sungmin; Lee, Chang Young; Choe, Wonyoung; Myung, Kyungjae; Park, Jang-Ung; Hong, Sung You Show More Hide
Wiley-Blackwell; WILEY-V C H VERLAG GMBH
Chemical Engineering; Chemistry; arylation; C@H activation; diaryliodonium salt; palladium; triphenylene
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article description
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 (dibenzylideneacetone) 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.