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Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates
Ambler, Brett R. Zhu, Lingui Altman, Ryan A.
Ambler, Brett R.
Zhu, Lingui
Altman, Ryan A.
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Abstract
Trifluoroethylarenes are found in a variety of biologically active molecules, and strategies for accessing this substructure are important for developing therapeutic candidates and biological probes. Trifluoroethylarenes can be directly accessed via nucleophilic trifluoromethylation of benzylic electrophiles; however, current catalytic methods do not effectively transform electron-deficient substrates and heterocycles. To address this gap, we report a Cu-catalyzed decarboxylative trifluoromethylation of benzylic bromodifluoroacetates. To account for the tolerance of sensitive functional groups, we propose an inner-sphere mechanism of decarboxylation.
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2015-08-21
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American Chemical Society
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Ambler, B. R., Zhu, L., & Altman, R. A. (2015). Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates. The Journal of Organic Chemistry, 80(16), 8449–8457. http://doi.org/10.1021/acs.joc.5b01343