An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C−H Bond Activations. Issue 18 (30th March 2017)

• Record Type: Journal Article
• Authors: 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
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 18(2017)
• Page Start: 5007
• Page End: 5011
• Publication Date: 2017-03-30
• Subjects: arylation -- C−H activation -- diaryliodonium salt -- palladium -- triphenylene; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201700405
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : Closing the circle : Palladium‐catalyzed 2‐ or 4‐fold C−H arylation of unactivated arenes was developed to access substituted triphenylene frameworks.