Electrochemical cascade access to hetero[8]circulenes as potent organophotocatalysts for diverse C-X bond formations.
basic_science · Level V
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- Record sourced from PubMed, PMID 40593683.
- Also identified by DOI 10.1038/s41467-025-60889-w and PMC identifier 12216941.
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Abstract
The chemistry of hetero[8]circulenes has been limited to three main types, constrained by synthetic challenges in creating unsymmetrical variants. Herein, we introduce an electrochemical approach to a type of hetero[8]circulene, featuring five hexagons and three pentagons. Our method capitalizes on the sustainability and selectivity of electrochemistry, utilizing differential oxidation potentials to generate dioxaza[8]circulenes through selective intermolecular and intramolecular couplings under mild conditions, achieving yields of up to 83% with good functional group tolerance. We further refine this process into a one-pot protocol using commercially available substrates, forming six new bonds. Comprehensive structural, optical, and electrochemical characterizations, including X-ray crystallography, spectrophotometric analysis, and DFT calculations, are conducted. Inspired by their distinct structural and redox properties, we explore the application of dioxaza[8]circulenes as organophotocatalysts for diverse C-X (X = C, B, S, P) bond formation achieving up to 97% yields under LED light irradiation (365 nm) without transition metals.