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

Fingerprint

Benzene Derivatives
Chemical activation
Graphite
Field effect transistors
Graphene
Benzene
Alcohols
Salts
Vapors
Derivatives
Sensors
triphenylene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

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. / An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C−H Bond Activations. In: Angewandte Chemie - International Edition. 2017 ; Vol. 56, No. 18. pp. 5007-5011.
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Mathew, BP, Yang, HJ, Kim, J, Lee, JB, Kim, YT, Lee, S, Lee, CY, Choe, W, Myung, K, Park, JU & Hong, SY 2017, 'An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C−H Bond Activations', Angewandte Chemie - International Edition, vol. 56, no. 18, pp. 5007-5011. https://doi.org/10.1002/anie.201700405

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

In: Angewandte Chemie - International Edition, Vol. 56, No. 18, 01.01.2017, p. 5007-5011.

Research output: Contribution to journalArticle

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