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Copper-Mediated Trifluoromethylation of α-Diazo Esters with TMSCF3: The Important Role of Water as a Promoter

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    Copper-Mediated Trifluoromethylation of α-Diazo Esters with TMSCF3: The Important Role of Water as a Promoter
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    Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, China
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    Cite this: J. Am. Chem. Soc. 2012, 134, 37, 15257–15260
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    https://doi.org/10.1021/ja307058c
    Published August 22, 2012
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    Copper-mediated trifluoromethylation of α-diazo esters with TMSCF3 reagent has been developed as a new method to prepare α-trifluoromethyl esters. This trifluoromethylation reaction represents the first example of fluoroalkylation of a non-fluorinated carbene precursor. Water plays an important role in promoting the reaction by activating the “CuCF3” species prepared from CuI/TMSCF3/CsF (1.0:1.1:1.1). The scope of this trifluoromethylation reaction is broad, and its efficiency is demonstrated in the synthesis of a variety of aryl-, benzyl-, and alkyl-substituted 3,3,3-trifluoropropanoates.

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    Cite this: J. Am. Chem. Soc. 2012, 134, 37, 15257–15260
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