191084-66-9

Upstream product

• 456-56-4 phenyl trifluoromethylsulfide 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 37772-00-2 N-(2,2,2-trifluoro-1-phenylethylidene)benzenamine 
• 100-65-2 N-Phenylhydroxylamine 
• 538-51-2 benzylidene phenylamine 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 62-53-3 aniline 
• 93-98-1 N-phenyl benzoyl amide 
• 1383851-01-1 3,5-bis(2',6'-dimethylphenyl)-1-mesitylpyridin-1-ium trifluoromethanesulfonate 
• 3262-89-3 triphenylboroxine 
• 1005385-45-4 N-(2,2,2-trifluoro-1-methoxyethyl)aniline 
• 2325-27-1 N-phenyltriphenyliminophosphorane 
• 622-37-7 Phenyl azide 

Downstream Products

• 293743-67-6 N-(phenyl)-N-(1,1,1-trifluoro-2-phenethyl)-4-methoxybenzamide 

Relevant academic research and scientific papers

Synthesis, structure, and thermolysis of tetracoordinated 1λ4,2-selenazetidines bearing two chiral centers at the 3-and 4-positions

The title trans and cis isomers (trans-3 and cis-3) were successfully synthesized as stable compounds by taking advantage of the Martin ligand. The X-ray crystallographic analysis of trans-3 showed that it has a distorted pseudotrigonal bipyramidal structure, and that the two phenyl groups at the 3-and 4-positions are cis to each other. The thermolysis of trans-3 in the presence of excess dimethyl acetylenedicarboxylate (DMAD) gave a mixture of the corresponding aziridines (trans-7 and cis-7) and cycloadducts (11a and 11b) of the azomethine ylides formed by ring opening of the aziridines with DMAD. Heating of cis-7 and excess DMAD under the same conditions gave diastereomeric mixtures of both the aziridines and the cycloadducts, which means that the stereochemistry of the aziridine formation from the 1,2-selenazetidine cannot be determined in this system.

Enantioselective Pd-catalyzed hydrogenation of fluorinated imines: Facile access to chiral fluorinated amines

An enantioselective hydrogenation of simple fluorinated imines has been developed using Pd(OCOCF3)2/(R)-Cl-MeO-BIPHEP as a catalyst, and up to 94% ee was achieved. This method provides an efficient route to enantioenriched fluorinated amines.

H2 Activation by Non-Transition-Metal Systems: Hydrogenation of Aldimines and Ketimines with LiN(SiMe3)2

In recent years, H2 activation at non-transition-metal centers has met with increasing attention. Here, a system in which H2 is activated and transferred to aldimines and ketimines using substoichiometric amounts of lithium bis(trimethylsilyl)amide is reported. Notably, the reaction tolerates the presence of acidic protons in the α-position. Mechanistic investigations indicated that the reaction proceeds via a lithium hydride intermediate as the actual reductant.

Iridium-Catalyzed Reductive Alkylations of Secondary Amides

Reported herein is the first direct, metal-catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method is shown to have exceptionally broad scope with respect to suitable nucleophiles, which cover both hard and soft C nucleophiles as well as a P nucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional groups.

Palladium(II)-Catalyzed Enantioselective Synthesis of α-(Trifluoromethyl)arylmethylamines

We describe a method for the synthesis of α-(trifluoromethyl)arylmethylamines that consists of the palladium(II)-catalyzed addition of arylboroxines to imines derived from trifluoroacetaldehyde. Palladium acetate is used as a catalyst with electron-neutral or electron-rich arylboroxines, and it was found that addition of an ammonium or silver salt was crucial to promote the reaction of electron-poor boroxines. With (S)-t-Bu-PyOX as the chiral ligand, this method delivers a variety of α-trifluoromethylated amines in 57-91% yield and with greater than 92% ee in most cases.

Pyridylidene-Mediated Dihydrogen Activation Coupled with Catalytic Imine Reduction

In recent years, dihydrogen activation at non-metallic centers has received increasing attention. A system in which dihydrogen is trapped by a pyridylidene intermediate that is generated from a pyridinium salt and a base is now reported. The dihydropyridi

Palladium(II)-catalyzed enantioselective synthesis of α- (trifluoromethyl)arylmethylamines

Trifluoromethylacetaldimines, generated in situ from the corresponding N,O-acetals, undergo 1,2-addition of arylboroxines under palladium(II) catalysis to generate a variety of α-(trifluoromethyl)arylmethylamines with good to high enantioselectivity (up to 97% ee). The pyridine-oxazolidine (PyOX) class of ligands was found to be particularly suitable for this transformation, which proceeds without exclusion of ambient air and moisture.

TTMPP-catalyzed trifluoromethylation of carbonyl compounds and imines with trifluoromethylsilane

A highly basic phosphine, tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP), catalyzes trifluoromethylation using trifluoromethyltrimethylsilane to give the corresponding trifluoromethylated products in good to high yields, with both carbonyl compounds and im

Nucleophilic trifluoromethylation of imines under acidic conditions

A general method for the trifluoromethylation of imines by using Me 3SiCF3 under acidic conditions is described. The reaction is promoted by hydrofluoric acid generated in situ from KHF2 and either TFA or TfOH. A new chemoselectivity pattern was achieved, as the C=N bond was found to be more reactivate than the carbonyl group. The trifluoromethylation reaction is believed to proceed by concerted transfer of the CF3 group from the silicon atom to the iminium electrophile. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Trifluoromethylation of non-activated aldimines with trimethyl(trifluoromethyl)silane in the presence of tetramethylammonium fluoride: A closer look into the reaction route

The reactions of non-activated aldimines with trimethyl(trifluoromethyl)silane and 1 equiv. of tetramethylammonium fluoride proceed via the formation of tetramethylammonium amides which were identified by low-temperature 19F NMR experiments. Consecutive reactions of the salts formed in situ with electrophiles yielded trifluoromethylated amines. Fluoride elimination is observed in the absence of electrophilic substrates leading to the formation of difluoromethylated ketimines.