Browsing by Subject "Photo-induced"

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    Dimsyl Anion Enables Visible‐Light‐Promoted Charge Transfer in Cross‐Coupling Reactions of Aryl Halides
    (Wiley, 2022-01) Pan, Lei; Cooke, Maria; Spencer, Amara; Laulhé, Sébastien; Chemistry and Chemical Biology, School of Science
    A methodology is reported for visible-light-promoted synthesis of unsymmetrical chalconides enabled by dimsyl anion in the absence of transition-metals or photoredox catalysts. The cross-coupling reaction between aryl halides and diaryl dichalconides proceeds with electron-rich, electron-poor, and heteroaromatic moieties. Mechanistic investigations using UV−Vis spectroscopy, time-dependent density functional theory (TD-DFT) calculations, and control reactions suggest that dimsyl anion forms an electron-donor-acceptor (EDA) complex capable of absorbing blue light, leading to a charge transfer responsible for generation of aryl radicals from aryl halides. This previously unreported mechanistic pathway may be applied to other light-induced transformations performed in DMSO in the presence of bases and aryl halides.