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Bottom‐up Construction of π‐Extended Arenes by a Palladium‐Catalyzed Annulative Dimerization of o ‐Iodobiaryl Compounds
Author(s) -
Zhu Chendan,
Wang Di,
Wang Dingyi,
Zhao Yue,
Sun WeiYin,
Shi Zhuangzhi
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201803603
Subject(s) - triphenylene , synthon , palladium , catalysis , chemistry , ligand (biochemistry) , combinatorial chemistry , cleavage (geology) , stereochemistry , organic chemistry , molecule , materials science , biochemistry , receptor , fracture (geology) , composite material
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.