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Angewandte Chemie v.130 no.29, 2018년, pp.8986 - 8991  

Bottom‐up Construction of π‐Extended Arenes by a Palladium‐Catalyzed Annulative Dimerization of o‐Iodobiaryl Compounds

Zhu, Chendan (State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China ) ; Wang, Di (State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China ) ; Wang, Dingyi (State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China ) ; Zhao, Yue (State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China ) ; Sun, Wei‐Yin (State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China ) ; Shi, Zhuangzhi (State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, N ) ;
  • 초록  

    Abstract 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 π‐systems in a controlled manner.


  • 주제어

    π-Erweiterung .   Arylierung .   Dimerisierung .   Kupplungsreaktionen .   Polycyclische aromatische Kohlenwasserstoffe (PAHs).  

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