Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 23, Pages 6935-6939Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201802445
Keywords
anthranils; ortho-ethynylbiaryls; polycyclic aromatic hydrocarbons; ring expansion; alpha-imino gold carbenes
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Funding
- Guangzhou Elite Scholarship Council
- CSC (China Scholarship Council)
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We describe a novel, short, and flexible approach to diverse N-doped polycyclic aromatic hydrocarbons (PAHs) through gold-catalyzed p-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 functionalgroup 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 violetblue fluorescence emission with quantum yields up to 0.45.
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