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

Bijoy P. Mathew, Hyun Ji Yang, Joohee Kim, Jae Bin Lee, Yun Tae Kim, Sungmin Lee, Chang Young Lee, Wonyoung Choe, Kyungjae Myung, Jang Ung Park, Sung You Hong

Research output: Contribution to journalArticle

35 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5007-5011
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number18
DOIs
Publication statusPublished - 2017 Jan 1

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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    Mathew, B. P., Yang, H. J., Kim, J., Lee, J. B., Kim, Y. T., Lee, S., Lee, C. Y., Choe, W., Myung, K., Park, J. U., & Hong, S. Y. (2017). An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C−H Bond Activations. Angewandte Chemie - International Edition, 56(18), 5007-5011. https://doi.org/10.1002/anie.201700405