Copper(0)-mediated fluoroalkylation of iodobenzene with 2-bromo-1,1,2,2-tetrafluoroethyl compounds: Investigation on the influence of R substituent on the reactivity of RCF2Cu species

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

“…Due to the unique physical, chemical and biological properties of organouorine compounds, the introduction of uorine atom(s) or uorinated moieties into organic molecules has become a routine strategy in drug design and advanced material development. [1][2][3][4] Among various uorinated functionalities, the tetrauoroethylene motif (-CF 2 CF 2 -) has attracted considerable attention because of its applications in agrochemicals 5 and liquid-crystalline materials. [6][7][8] Moreover, the introduction of -CF 2 CF 2group into liquid crystals oen results in highly advantageous properties such as high clearing temperature, broad nematic phase range, low rotational viscosity and high dielectric anisotropy.…”

“…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). As such, developing a new method to incorporate -CF 2 CF 2structure motif into organic molecules with readily available, easy to handle and environmentally benign reagents under mild conditions is highly desired.…”

Advances in the Synthesis and Application of Tetrafluoroethylene‐ and 1,1,2,2‐Tetrafluoroethyl‐Containing Compounds

“…The Hu group later described similar Cu 0 ‐mediated coupling of iodobenzene with equimolar amount of tetrafluoroalkyl bromides in low to good yields (Scheme ). The amount of copper powder was overstoichiometric (2 equiv).…”

Ru(bpy)3Cl2 as a Photocatalyst for Visible‐Light‐Induced Fluoroalkylation of Anilines with BrCF2CF2Br: A Facile Route to 2‐Bromo‐1,1,2,2‐tetrafluoroethyl Arenes

“…Generally, the structure of ArCF 2 CF 2 R, is prepared via fluorination methods, such as fluorine addition to arylacetylenes or deoxofluorination of 1,2‐dicarbonyl compounds. Recently, some new protocols to access to this formula were developed by Gouverneur, Togni, Beier, Hu, and Cho . In those reactions, ArCF 2 CF 2 Br, ArCF 2 CF 2 SiMe 3 and hypervalent iodine reagents were used as fluoroalkylated reagents.…”