1350433-03-2

Upstream product

• 100-10-7 4-dimethylamino-benzaldehyde 
• 887144-94-7 Togni's reagent II 
• 41463-93-8 4-N,N-dimethylaminobenzaldehyde hydrazone 
• 75-88-7 1,1,1-trifluoro-2-chloroethane 
• 7353-91-5 4-dimethylaminophenylmagnesium bromide 
• 353-83-3 1,1,1-trifluoro-2-iodoethane 
• 38935-94-3 4-dimethylamino-β,β-difluorostyrene 

Relevant academic research and scientific papers

Cobalt/diamine-catalyzed 1,1-difluoroethylation and 2,2,2-trifluoroethylation of aryl Grignard reagents with corresponding fluoroalkyl halides

Cobalt/diamine-catalyzed 1,1-difluoroethylation and 2,2,2-trifluoroethylation of aryl Grignard reagents with 1,1-difluoroethyl and 2,2,2-trifluoroethyl halides were investigated. With regard to the 1,1-difluoroethylation, 1,2-bis(dimethylamino)-2-methylpropane, which has been rarely used in the cross-coupling reactions, gave the highest yield among the diamine ligands tested. In the 2,2,2-trifluoroethylation, trans-1,2-bis(dimethylamino)cyclohexane provided the desired products in satisfactory yields with not only 2,2,2-trifluoroethyl iodide but also chloride. This Co/diamine catalyst was also effective for the coupling with other partially fluorinated alkyl halides in the presence of appropriate diamine ligands.

Denitrogenative Hydrotrifluoromethylation of Benzaldehyde Hydrazones: Synthesis of (2,2,2-Trifluoroethyl)arenes

Reacting hydrazones of arylaldehydes with Togni's CF3-benziodoxolone reagent, in the presence of potassium hydroxide and cesium fluoride, induces a denitrogenative hydrotrifluoromethylation event to produce (2,2,2-trifluoroethyl)arenes. This novel reaction was tolerant to many electronically-diverse functional groups and substitution patterns, as well as naphthyl- and heteroaryl-derived substrates. Advantages of this process include the easy access to hydrazone precursors on a large scale, speed and operational simplicity, and being transition metal-free.

METHOD FOR PRODUCING (FLUOROALKYL) ARENE

PROBLEM TO BE SOLVED: To provide a method for efficiently producing fluoroalkyl arene, which is important as synthetic raw materials for medicines and functional materials. SOLUTION: A fluoroalkyl arene is produced by the reaction between an aryl metal species represented by formula (2) and a fluoroalkyl halide represented by formula (3) in the presence of a cobalt compound and an ethylenediamine derivative. In the formula (2) shown in the following figure, R11-R15 independently represent H, a C1-C4 alkyl group or the like. In the formula (3): Y-Rf, Y is Cl or the like; Rf is a C2-C3 fluoroalkyl group. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

A simple, rapid procedure for nucleophilic radiosynthesis of aliphatic [18F]trifluoromethyl groups

A procedure for the radiosynthesis of aliphatic [18F] trifluoromethyl groups by reacting 1,1-difluorovinyl precursors with [ 18F]fluoride ions, resulting in the equivalent of direct nucleophilic addition of H[18F]F, has been developed. A variety of 18F-labelled model compounds were then obtained and two potential [18F]radiotracers were synthesised by a two step process starting from 1,1-difluorovin-2-yl 4-toluenesulfonate. The method is widely applicable for the synthesis of novel radiotracers in high radiochemical yields and good specific activity.