Copper-mediated trifluoromethylation of α-diazo esters with TMSCF3: the important role of water as a promoter.
Copper-mediated trifluoromethylation of α-diazo esters with TMSCF(3) 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 "CuCF(3)" species prepared from CuI/TMSCF(3)/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.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, China.
Mingyou
M
Hu
Chuanfa
C
Ni
Jinbo
J
Hu
D001391:Azo Compounds / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D004952:Esters; D008745:Methylation; D014867:Water / Q000737:chemistry*
D001391:Azo Compounds; D004952:Esters; D014867:Water; D003300:Copper