Gold‐Catalyzed Regiospecific C−H Annulation of o‐Ethynylbiaryls with Anthranils: π‐Extension by Ring‐Expansion En Route to N‐Doped PAHs |
| |
| Authors: | Zhongyi Zeng Hongming Jin Dr Kohei Sekine Dr Matthias Rudolph Frank Rominger Prof?Dr A Stephen K Hashmi |
| |
| Affiliation: | 1. http://www.hashmi.de;2. Organisch-Chemisches Institut, Heidelberg University, Heidelberg, Germany;3. Chemistry Department, Faculty of Science, King Abdulaziz University (KAU), Jeddah, Saudi Arabia |
| |
| Abstract: | 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. |
| |
| Keywords: | anthranils ortho-ethynylbiaryls polycyclic aromatic hydrocarbons ring expansion α -imino gold carbenes |
|
|
