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Gold‐Catalyzed Regiospecific C−H Annulation of o ‐Ethynylbiaryls with Anthranils: π‐Extension by Ring‐Expansion En Route to N‐Doped PAHs
Author(s) -
Zeng Zhongyi,
Jin Hongming,
Sekine Kohei,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2018
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.201802445
Subject(s) - annulation , catalysis , nucleophile , ring (chemistry) , chemistry , reagent , atom economy , tandem , combinatorial chemistry , friedel–crafts reaction , fluorescence , photochemistry , organic chemistry , materials science , physics , quantum mechanics , composite material
We describe a novel, short, and flexible approach to diverse N‐doped polycyclic aromatic hydrocarbons (PAHs) through gold‐catalyzed π‐extension of anthranils with o ‐ethynylbiaryls as reagents. This strategy uses easily accessible starting materials, is simple due to high step and atom economy, and shows good functional‐group compatibility as well as scale‐up potential. Mechanistically, the tandem reaction is proposed to involve a nucleophilic addition/ring opening/regiospecific C−H annulation/protodeauration sequence terminated by a Friedel–Crafts‐type cyclization. Photophysical studies of the products indicated violet‐blue fluorescence emission with quantum yields up to 0.45.