Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 29, Pages 8848-8853Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201803603
Keywords
pi-extension; arylation; coupling; dimerization; polycyclic aromatic hydrocarbons (PAHs)
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Funding
- 1000-Youth Talents Plan
- NSF of China [2167020084]
- Innovation & Entrepreneurship Talents Plan of Jiangsu Province
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A straightforward method was developed for construction of aromatic compounds with a triphenylene core. The method involves Pd-catalyzed annulative dimerization of o-iodobiaryl compounds by double C-I and C-H bond cleavage steps. Simple reaction conditions are needed, requiring neither a ligand nor an oxidant, and the reaction tolerates a wide range of coupling partners without compromising efficiency or scalability. Significantly, the tetrachloro-substituted synthon, 1,6,11-trichloro-4-(4-chlorophenyl)triphenylene, can be generated and used to prepare a series of fully fused, small graphene nanoribbons by a late-stage arylation with arylboronic acids and a subsequent Scholl reaction. The synthetic strategy enables bottom-up access to extended -systems in a controlled manner.
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