Journal of the American Chemical Society, 133(51), 20901-20913 (2011-12-06)
We have found the first reaction of direct cupration of fluoroform, the most attractive CF(3) source for the introduction of the trifluoromethyl group into organic molecules. Treatment of CuX (X = Cl, Br, I) with 2 equiv of MOR (M
CF(3)-substituted vinyl diphenylsulfonium triflate is an effective annulation reagent for the formation of α-CF(3) substituted, epoxide-fused heterocycles (pyrrolidines, piperidines, and tetrahydrofurans). This simple method affords a variety of valuable heterocyclic building blocks in a highly diastereoselective manner (dr >20:1).
Silver and copper ethylene adducts and the silver carbonyl complex of the tris(pyrazolyl)borate [HB(3,4,5-(CF(3))(3)Pz)(3)](-) (which is based on one of the most acidic pyrazoles known) have been synthesized. (13)C NMR resonance signals of metal-bound ethylene carbon atoms of [HB(3,4,5-(CF(3))(3)Pz)(3)]Ag(C(2)H(4)) and
The Journal of organic chemistry, 75(19), 6581-6587 (2010-08-31)
The mechanism of ring-opening of ε-caprolactone by methanol catalyzed by trifluoromethane and methane sulfonic acids has been studied computationally at the DFT level of theory. For both elementary steps, the sulfonic acid was predicted to behave as a bifunctional catalyst.
The Journal of organic chemistry, 77(24), 11383-11387 (2012-11-22)
A method for trifluoromethylation of alkenes has been developed employing visible light photoredox catalysis with CF(3)I, Ru(Phen)(3)Cl(2), and DBU. This process works especially well for terminal alkenes to give alkenyl-CF(3) products with only E-stereochemistry. The mild reaction conditions enable the
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