Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 37, Pages 15257-15260Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja307058c
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Funding
- National Basic Research Program of China [2012CB821600, 2012CB215500]
- National Natural Science Foundation of China [20825209, 20832008]
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Copper-mediated trifluoromethylation of alpha-diazo esters with TMSCF3 reagent has been developed as a new method to prepare alpha-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 Cull 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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