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Nucleophilic Ring Opening of Donor–Acceptor Cyclopropanes Catalyzed by a Brønsted Acid in Hexafluoroisopropanol

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journal contribution
posted on 18.01.2018, 18:07 by Edward Richmond, Vuk D. Vuković, Joseph Moran
A general, Brønsted acid catalyzed method for the room temperature, nucleophilic ring opening of donor–acceptor cyclopropanes in fluorinated alcohol solvent, HFIP, is described. Salient features of this method include an expanded cyclopropane scope, including those bearing single keto-acceptor groups and those bearing electron-deficient aryl groups. Notably, the catalytic system proved amenable to a wide range of nucleophiles including arenes, indoles, azides, diketones, and alcohols.