Copper-catalyzed trifluoromethylations

Parsons AT, Buchwald SL (2011) Copper-catalyzed trifluoromethylation of unactivated ole-flns. Angew Chem Int Ed 50 9120-9123. doi 10.1002/anie.201104053... 

Shen in 2012 reported an Ir/Cu synergistic catalytic C—H bond activation for the one-pot trifluoromethylation reaction (Scheme 9.19). This catalytic process involves sequential iridium-catalyzed C—activation borylation and copper-catalyzed trifluoromethylation of arenes with a variety of functional groups. This tandem procedure was successfully applied to the 2,6-disubstituted pyridine, benzofuran, benzothiazole, indole, and substituted quinoline systems. 

Ye Y, Sanford MS (2012) Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed trifluoromethylation of boronic acids with CF3I. J Am Chem Soc 134 9034-9037... 

Liu T, Shen Q (2011) Copper-catalyzed trifluoromethylation of aryl and vinyl boronic acids with an electrophilic trifluoromethylating reagent. Org Lett 13 2342-2345... 

Recently, simple copper-catalyzed trifluoromethylation of aryl boronic acids under mild conditions was developed. Using (trifluoromethyl)trimethylsilane (McsSiCFs) [93], trifluoromethyldibenzothiophenium triflate [94], or Togni s reagent [95], 2-trifluoromethylbenzo[fc]thiophene 173 was prepared in 45-73 % yields. 

Xu J, Luo DF, Xiao B, liu ZJ, Gong TJ, Fu Y, liu L (2011) Copper-catalyzed trifluoromethylation of aryl boronic adds using a CF3 reagent. Chem Comm 47 4300-4302... 

The copper-catalyzed trifluoromethylation of iV-phenyl-2-iodoimidazole and A-methyl-2-iodobenzimidazole using 5 -(trifluoromethyl)diphenyl iodonium triflate afforded the corresponding C-2 trifluoromethylated derivatives in 85-90 % yields (Scheme 1) [8], Interestingly, the trifluoromethylation of iV-tritylimidazole failed, even at 80 °C, presumably due to the steric effect of the trityl group. 

Li Y, Wu L, Neumann H, Beller M (2013) Copper-catalyzed trifluoromethylation of aryl- and vinylboronic acids with generation of CFa-radicals. Chem Commun 49 2628-2630... 

SCHEME 26.25. Copper-catalyzed trifluoromethylation using an electrophilic trifluoromethylating reagent. 

Weng Z, Lee R, Jia W, Yuan Y, Wang W, Feng X, Huang KW. Cooperative effect of silver in copper-catalyzed trifluoromethylation of aryl iodides using MesSiCFs. Organometal-... 

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