A palladium-catalyzed Barluenga cross-coupling - reductive cyclization sequence to substituted indoles.
Tetrahedron
; 942021 Aug.
Article
em En
| MEDLINE
| ID: mdl-34483377
ABSTRACT
A short and flexible synthesis of substituted indoles employing two palladium-catalyzed reactions, a Barluenga cross-coupling of p-tosylhydrazones with 2-nitroarylhalides followed by a palladium-catalyzed, carbon monoxide-mediated reductive cyclization has been developed. A one-pot, two-step methodology was further developed, eliminating isolation and purification of the cross-coupling product. This was accomplished by utilizing the initially added 0.025 equivalents of bis(triphenylphosphine)palladium dichloride, thus serving a dual role in the cross-coupling and the reductive cyclization. It was found that addition of 1,3-bis(diphenylphosphino)propane and carbon monoxide after completion of the Barluenga reaction afforded, in most cases, significantly better overall yields.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Tetrahedron
Ano de publicação:
2021
Tipo de documento:
Article
País de afiliação:
Estados Unidos