Browsing by Author "Deckert, Macy M."

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    Solvent Anions Enable Photoinduced Borylation and Phosphonation of Aryl Halides via EDA Complexe
    (American Chemical Society, 2022) Pan, Lei; Deckert, Macy M.; Cooke, Maria Victoria; Bleeke, Annika R.; Laulhé, Sébastien; Chemistry and Chemical Biology, School of Science
    We report the synthesis of aryl boronic esters and aryl phosphonate esters promoted by visible-light in the absence of transition-metals or photoredox catalysts. The transformation proceeds at room temperature using sodium hydride, as a non-nucleophilic base, and exhibits functional group tolerance for anilines, amides, and esters. UV-vis spectroscopy, radical trapping experiments, and computational (TD-DFT) calculations suggest an electron-donor-acceptor (EDA) complex between solvent anions and aryl halides as the species responsible for this reactivity.
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    Transition-Metal-Free Photoredox Phosphonation of Aryl C–N and C–X Bonds in Aqueous Solvent Mixtures
    (American Chemical Society, 2022) Pan, Lei; Kelley, Alexandra S.; Cooke, Maria Victoria; Deckert, Macy M.; Laulhé, Sébastien; Chemistry and Chemical Biology, School of Science
    Herein, we present an efficient and mild methodology for the synthesis of aromatic phosphonate esters in good to excellent yields using 10H-phenothiazine, an inexpensive commodity chemical, as a photoredox catalyst. The reaction exhibits wide functional group compatibility enabling the transformation in the presence of ketone, amide, ester, amine, and alcohol moieties. Importantly, the reaction proceeds using a green solvent mixture primarily composed of water, thus lowering the environmental footprint of this transformation compared to current methods. The transformation also proceeds under atmospheric conditions, which further differentiates it from current methods that require inert atmosphere. Mechanistic work using fluorescence quenching experiments and radical trapping approaches support the proposed mechanism.