Zeng Zhongyi, Jin Hongming, Sekine Kohei, Rudolph Matthias, Rominger Frank, Hashmi A Stephen K
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Chemistry Department, Faculty of Science, King Abdulaziz University (KAU), 21589, Jeddah, Saudi Arabia.
Angew Chem Int Ed Engl. 2018 Jun 4;57(23):6935-6939. doi: 10.1002/anie.201802445. Epub 2018 May 8.
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.
我们描述了一种新颖、简短且灵活的方法，通过以邻乙炔基联芳基为试剂，利用金催化邻氨基苯甲腈的π-扩展反应来合成多种氮掺杂多环芳烃（PAHs）。该策略使用易于获得的起始原料，由于具有高的步骤经济性和原子经济性而操作简单，并且显示出良好的官能团兼容性以及放大潜力。从机理上讲，该串联反应被认为涉及亲核加成/开环/区域特异性C-H环化/脱金反应序列，并以傅克型环化反应终止。对产物的光物理研究表明，其发出紫蓝色荧光，量子产率高达0.45。
