Divergent Construction of N-Doped Polycyclic Aromatic Hydrocarbons with Indole as the Nitrogen Source Building Block.
Chemistry
; 29(22): e202300140, 2023 Apr 18.
Article
em En
| MEDLINE
| ID: mdl-36705339
ABSTRACT
An Ag/Au-catalyzed divergent cascade reaction of alkyne embedded diazoketones with indoles has been described. Preliminary mechanistic studies indicate that the reaction goes through a [4+2]-cycloaddition of an inâ
situ formed isobenzopyrylium intermediate with indole, followed by a sequential retro-Michael addition/carbene N-H insertion process to give the benzo[i]phenanthridines products with gold catalysis; whereas a dearomatization/rearomatization sequence occurs favourably when the reaction is catalyzed by a silver catalyst, delivering benzo[b]carbazoles in generally high to excellent yields. Notably, this is a rare example of using indole as the dienophile for cycloaddition with the isobenzopyrylium species, providing a concise and practical approach for the selective construction of N-doped polycyclic aromatic hydrocarbons (PAHs) with structural diversity and broad functional-group compatibility.
Texto completo:
1
Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2023
Tipo de documento:
Article