Trifluoromethylcopper: a useful difluoromethylene transfer reagent: a novel double insertion of difluoromethylene into pentafluorophenylcopper

The Trifluoromethyl Group in Transition Metal Chemistry

“…[131] In this reaction there is no evidence of any free difluorocarbene intermediate; the authors instead suggested the existence of an equilibrium between CF 3 Cu and CF 2 =CuF (cf. For instance, a double CF 2 -insertion reaction into Cu-C bonds has been reported to occur in the reaction between C 6 F 5 Cu and CF 3 Cu (generated in situ at room temperature) to yield C 6 F 5 CF 2 CF 2 Cu.…”

Controllable double CF2-insertion into sp2 C–Cu bond using TMSCF3: a facile access to tetrafluoroethylene-bridged structures

“…Current methods for the syntheses of tetrauoroethylenebridged structures are mainly based on (1) deoxouorination of 1,2-dicarbonyl compounds with SF 4 and DeoxoFluor; [9][10][11] (2) uorination of C-C triple bonds using F 2 ; [12][13][14] (3) 1,2-difunctionalization of tetrauoroethylene (TFE); [15][16][17][18][19][20][21][22][23] (4) diuoromethylene insertion using CF 2 Br 2 as the CF 2 source; 24,25 and (5) using RCF 2 CF 2 Br as the build block. 5 However, these methods suffer from several drawbacks such as (1) using toxic, highly reactive or hazardous reagents; (2) low functional group tolerance and/or (3) using explosive gaseous reagents or ozonedepleting substances (ODS).…”

Polyfluoroaromatic Compounds

“…A remarkable double insertion of difluorocarbene, derived from trifluoromethyl copper, has been reported [227] (Figure 9.87).…”