Oxytrifluoromethylation of multiple bonds using copper catalyst under mild conditions

Recent progress in the trifluoromethylation of alkenes with Togni's reagents

“…33,34 Szabó et al showed that alkenes undergo smooth addition reactions with Togni's reagent 1 using CuI as catalyst. 32 The reaction proceeds with higher yield, high regioselectivity and more cleanly for electron-rich styrenes.…”

“…Sodeoka and co-workers 34 showed that oxytrifluoromethylation reaction of styrene derivatives was achieved with high efficiency in the presence of [(MeCN) 4 Cu]PF 6 catalyst and Togni's reagent 1. Oxytrifluoromethylation of styrene derivatives bearing an oxygen atom or no heteroatom on a phenyl ring and N-protected aniline derivatives proceeded smoothly to give the corresponding products in high yields.…”

Effects of B2pin2 and PCy3 on copper-catalyzed trifluoromethylation of substituted alkenes and alkynes with the Togni reagent

“…50e52 The electron-rich Cu-atom in 10 may undergo efficient oxidative addition with 1a to form Cu(III) complex 11. Many previous studies have shown 15,17,21,29,56 that the copper-catalyzed trifluoromethylation reactions with 1a are inhibited by radical traps, for example, TEMPO. This indicates that the reaction proceeds via CF 3 radicals.…”

“…1e3 Oxytrifluoromethylation of alkenes and alkynes attracted a particularly broad attention. Independent studies by Sodeoka, 15 Loh 16 and our group 17 have presented the first copper-catalyzed oxytrifluoromethylation of alkenes and alkynes using the Togni, 1,18 and related reagents, 14 1aec. These studies have been followed by excellent work on copper-catalyzed intramolecular oxytrifluoromethylation by Buchwald 19 and Liang 20 and the difunctionalization based trifluoromethylation processes have been extended to carbon, 16,21e24 nitrogen, 25 and other substituents 26,27 as well.…”

Facile synthesis of (E)-β-(trifluoromethyl)styrenes from halothane (HCFC-123B1)

“…However, this type of reaction has mainly two disadvantages: (i) low stereoselectivity and (ii) narrow scope of substrates (aromatic aldehydes are employed, in general). Another method involves the transition-metal-mediated coupling reaction (Type II) [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28]. Taking the incessant emergence of well-elaborated procedures into account, it appears that the syntheses of trifluoromethylated alkenes have incorporated this methodology.…”