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

• DOI: 10.1021/ja307058c
• Publication Date: 2012-08-22T21:40:27Z
• Authors: Mingyou Hu; Chuanfa Ni; Jinbo Hu
• Keywords: Trifluoromethylation

Copper-mediated trifluoromethylation of α-diazo esters with TMSCF3 reagent has been developed as a new method to prepare α-trifluoromethyl esters. This reaction represents the first example fluoroalkylation non-fluorinated carbene precursor. Water plays an important role in promoting by activating “CuCF3” species prepared from CuI/TMSCF3/CsF (1.0:1.1:1.1). The scope this is broad, and its efficiency demonstrated synthesis variety aryl-, benzyl-, alkyl-substituted 3,3,3-trifluoropropanoates.