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Browsing by Subject "Aryl boronic esters"
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Item 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 ScienceWe 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.