Decoupled EDA Activation of Aryl Halides Enables Metal-Free C-H Arylation of Pyrroles.

Authors

Ashutosh Mishra, Sakthi Raje, Priya Mata, Graham de Ruiter

Published in

Chemistry (Weinheim an der Bergstrasse, Germany). Pages e71660. Sep 22, 2026. Epub Sep 22, 2026.

Abstract

Electron donor-acceptor (EDA) complexes have emerged as a powerful platform for photocatalyst-free, visible-light-driven radical-based synthesis. However, existing strategies are typically limited by binary activation modes in which the electron donor also serves as the nucleophilic coupling partner, restricting synthetic modularity. Here we report a decoupled EDA strategy in which N,N-dimethylaniline (DMA) acts as a dedicated electron donor, forming a photoactive charge-transfer complex with electron-deficient (hetero)aryl halides under visible-light irradiation. Photoinduced single-electron transfer promotes C─X bond fragmentation to generate aryl radicals that are intercepted by independently chosen coupling partners, enabling C-H arylation of pyrroles. The method is applicable to aryl bromides, iodides, and activated aryl chlorides, and extends to borylation and hydrodehalogenation by simple variation of the radical trap. These results demonstrate that decoupled EDA activation provides a modular platform for metal-free C─C bond formation from aryl halides.

PMID:
42770672
Bibliographic data and abstract were imported from PubMed on 22 Sep 2026.

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