Literature DB >> 26225803

Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates.

Brett R Ambler1, Lingui Zhu1, Ryan A Altman1.   

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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Year:  2015        PMID: 26225803      PMCID: PMC4546558          DOI: 10.1021/acs.joc.5b01343

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  22 in total

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8.  The first Cu(I)-mediated nucleophilic trifluoromethylation reactions using (trifluoromethyl)trimethylsilane in ionic liquids.

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  7 in total

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2.  Catalytic One-Step Deoxytrifluoromethylation of Alcohols.

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Journal:  J Org Chem       Date:  2019-01-25       Impact factor: 4.354

3.  Metallaphotoredox Perfluoroalkylation of Organobromides.

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4.  Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers.

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6.  Aqueous Benzylic C-H Trifluoromethylation for Late-Stage Functionalization.

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7.  Interrupting the Barton-McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation of O-Alkyl Thiocarbonates.

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  7 in total

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