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Construction of Cationic Azahelicenes: Regioselective Three‐Component Annulation Using In Situ Activation Strategy
Author(s) -
Wang Zhishuo,
Jiang Linfeng,
Ji Jinwen,
Zhou Fulin,
Lan Jingbo,
You Jingsong
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202010051
Subject(s) - isoquinoline , annulation , regioselectivity , cationic polymerization , chemistry , in situ , combinatorial chemistry , solvent , stereochemistry , organic chemistry , catalysis
Described herein is a strategy to construct cationic azahelicenes through the three‐component annulation reaction of isoquinoline, indole, and 1,2‐dichloroethane (DCE), in which DCE serves as an in situ activating agent for C1−H activation of isoquinoline, a vinyl equivalent, and a solvent. This in situ activation annulation reaction features a facile one‐step synthesis and complete regioselectivity. The complete regioselectivity of C1 over C3 for the isoquinoline ring paves a path to the helical structure in a highly ordered sequence. One of the synthesized ionic [5]azahelicenium fluorophores exhibits the potential to serve as a mitochondria‐targeted biomarker with good photostability and low cytotoxicity.