Tunable Regioselectivity in C-H-Activated Direct Arylation Reactions of Dithieno[3,2-b:2',3'-d]pyrroles.

Autor: Vogt A; Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081, Ulm, Germany., Stümpges F; Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081, Ulm, Germany., Bajrami J; Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081, Ulm, Germany., Baumgarten D; Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081, Ulm, Germany., Millan J; Dpto. de Química - Facultad de Ciencia y Tecnología, Universidad de La Rioja, Madre de Dios 53, 26006, Logroño-La Rioja, España., Mena-Osteritz E; Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081, Ulm, Germany., Bäuerle P; Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081, Ulm, Germany.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2023 Oct 26; Vol. 29 (60), pp. e202301867. Date of Electronic Publication: 2023 Sep 04.
DOI: 10.1002/chem.202301867
Abstrakt: In this study, regioselectively controlled direct arylation of dithieno[3,2-b:2,3'-d]pyrroles (DTPs) is reported. By carefully selecting the catalytic system, Pd source, ligand, and additives, we achieved either selective N-arylation or unprecedented β-arylation and β,β'-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 β-aryl, β,β'-diaryl, α-aryl, and α,α'-diaryl scaffolds. These compounds can be straightforwardly prepared and further functionalized for applications as organic electronic materials.
(© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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