Tunable Regioselectivity in C-H-Activated Direct Arylation Reactions of Dithieno[3,2-b:2',3'-d]pyrroles.
Chemistry
; 29(60): e202301867, 2023 Oct 26.
Article
em En
| MEDLINE
| ID: mdl-37667450
ABSTRACT
In this study, regioselectively controlled direct arylation of dithieno[3,2-b2,3'-d]pyrroles (DTPs) is reported. By carefully selecting the catalytic system, Pd source, ligand, and additives, we achieved either selective N-arylation or unprecedented ß-arylation and ß,ß'-diarylation of the DTP core through C-H activation when reacting unsubstituted H-DTP with 9-anthracenyl halides. For N-substituted DTPs, we obtained regioselective carboxylate-assisted arylation of the α-position(s). Consequently, depending on the catalytic system and substitution at the DTP nitrogen, we successfully synthesized novel regioselectively substituted DTPs, including N-aryl, rarely reported ß-aryl, ß,ß'-diaryl, α-aryl, and α,α'-diaryl scaffolds. These compounds can be straightforwardly prepared and further functionalized for applications as organic electronic materials.
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Base de dados:
MEDLINE
Idioma:
En
Revista:
Chemistry
Assunto da revista:
QUIMICA
Ano de publicação:
2023
Tipo de documento:
Article
País de afiliação:
Alemanha