A simple strategy avoiding the decomposition of a naked trifluoromethyl anion to difluorocarbene by a sterically very demanding organo-superbase without the help of a trifluoromethyl anion reservoir such as DMF is reported. The direct non-metallic trifluoromethylation of carbonyl compounds using fluoroform in the presence of t-Bu-P4 base afforded trifluoromethyl alcohols in high yields.

An MT-sulfone group was converted to a trifluoromethyl group by treatment with IF(5) after an alkylation reaction. Therefore, an MT-sulfone anion can be used as a trifluoromethyl anion equivalent. The formal asymmetric Michael-addition of a trifluoromethyl anion to crotonaldehyde was also performed.

The highly enantioselective dienamine-mediated formation of 5-bromo-6-(trifluoromethyl)-3,4-dihydro-2H-pyrans from α,β-unsaturated aldehydes and α-bromo-(trifluoromethyl)-enones employing a C2-symmetric aminocatalyst is described. The products are demonstrated to be applicable in coupling reactions directly onto the ring, thereby granting access to a broad scope of highly substituted 6-(trifluo...

Functionalized 3-trifluoromethyl-2-isoxazolines and 3-trifluoromethylisoxazoles were easily prepared from trifluoromethyl aldoxime 2 under mild conditions by using DIB as oxidant. Theoretical studies of the reactivity of trifluoroacetonitrile oxide 4 toward olefins and alkynes were carried out. The 3-trifluoromethyl-2-isoxazolines were ring-opened with NaBH4 and NiCl2 to yield the corresponding...

Abstract A methodology for the oxidation of α-trifluoromethyl alcohols to corresponding trifluoromethyl ketones is presented. catalytic quantity a nitroxide used, and potassium persulfate serves as terminal oxidant. The proves effective aromatic, heteroaromatic, conjugated alcohol substrates. It can be extended nonfluorinated secondary and, in this case, applied range aliphatic alcohols.

Treating 1,5-difluoro-2,4-dinitrobenzene (1) with N1-phenyl-5-(trifluoromethyl)benzene-1,2diamine (4) and N,N-diisopropylethylamine in EtOH at ca. 0 ◦C for 4 h affords a mixture of N1-(5-ethoxy-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (5) (38%) and N1-(5-fluoro-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (6) (51%) that can be separated by chrom...

Ambient light stable 3-trifluoromethyl-3-aryldiazirine photolabels are developed via stabilization of the strained three membered diazirine ring by replacing the phenyl ring with electron withdrawing heterocyclic rings. Photolabeling studies reveal that these ambient light stable photolabels are equally efficient in photolabeling target proteins as the traditional 3-trifluoromethyl-3-phenyldiaz...

A variety of aromatic trifluoromethyl ketone derivatives has been studied as inhibitors of apoptosis in cerebellar granule neurons (CGNs). Among them, alpha-trifluoromethyl diketone (2) and benzyl trifluoromethyl ketone (11) were found to be apoptosis inhibitors which can prevent a neurodegenerative disease. Compounds 2 and 11 showed neuroprotection effect on low K+-induced apoptosis in CGNs. F...

2-Trifluoromethyl-5-(arylsulfonyl)methyl pyrroles and 2-trifluoromethyl-4-(arylsulfonyl)methyl pyrroles were selectively synthesized from trifluoromethyl-substituted 3-aza-1,5-enynes via a cyclization/sulfonyl group migration cascade catalyzed by AgOOCCF3 and CsOPiv, respectively. Alkylvinyl-substituted pyrroles were generated from seven-atom skeleton 3-aza-1,5-enynes via aryl sulfinic acid eli...