114467-75-3

Upstream product

• 637-87-6 1-Chloro-4-iodobenzene 
• 130754-19-7 ethyl 4-chlorophenyl-2,2-difluoroacetate 
• 98-56-6 4-chlorobenzotrifluoride 
• 104-88-1 4-chlorobenzaldehyde 
• 43141-66-8 1-chloro-4-(difluoromethyl) benzene 

Downstream Products

• 114467-91-3 1-Chloro-4-(difluoro-isocyanato-methyl)-benzene 
• 114467-88-8 1-(Azido-difluoro-methyl)-4-chloro-benzene 
• 1188475-53-7 C₄₁H₃₉ClF₂O₆ 
• 114467-93-5 1-Chloro-4-(difluoro-isothiocyanato-methyl)-benzene 
• 114467-83-3 1-Chloro-4-(difluoro-phenoxy-methyl)-benzene 
• 114467-79-7 1-Chloro-4-(difluoro-phenylsulfanyl-methyl)-benzene 

Relevant academic research and scientific papers

Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination

Herein we report the copper-catalyzed silylation of propargylic difluorides to generate axially chiral, tetrasubstituted monofluoroallenes in both good yields (27 examples >80%) and enantioselectivities (82-98% ee). Compared to previously reported synthetic routes to axially chiral allenes (ACAs) from prochiral substrates, a mechanistically distinct reaction has been developed: the enantiodiscrimination between enantiotopic fluorides to set an axial stereocenter. DFT calculations and vibrational circular dichroism (VCD) suggest that β-fluoride elimination from an alkenyl copper intermediate likely proceeds through a syn-β-fluoride elimination pathway rather than an anti-elimination pathway. The effects of the C1-symmetric Josiphos-derived ligand on reactivity and enantioselectivity were investigated. Not only does this report showcase that alkenyl copper species (like their alkyl counterparts) can undergo β-fluoride elimination, but this elimination can be achieved in an enantioselective fashion.

Iron-Catalyzed Halogen Exchange of Trifluoromethyl Arenes**

The facile production of ArCF2X and ArCX3 from ArCF3 using catalytic iron(III)halides is reported, which constitutes the first iron-catalyzed halogen exchange for non-aromatic C?F bonds. Theoretical calculations suggest direct activation of C?F bonds by iron coordination. ArCX3 and ArCF2X products of the reaction are synthetically valuable due to their diversification potential. In particular, chloro- and bromodifluoromethyl arenes (ArCF2Cl, ArCF2Br respectively) provide access to a myriad of difluoromethyl arene derivatives (ArCF2R). To optimize for mono-halogen exchange, a statistical method called Design of Experiments was used. Optimized parameters were successfully applied to electron rich and electron deficient aromatic substrates, and to the late stage diversification of flufenoxuron, a commercial insecticide. These methods are highly practical, being run at convenient temperatures and using inexpensive common reagents.

Frustrated Lewis-Pair-Meditated Selective Single Fluoride Substitution in Trifluoromethyl Groups

Single fluoride substitution in trifluoromethylarenes is an ongoing synthetic challenge that often leads to "over-reaction", where multiple fluorides are replaced. Development of this reaction would allow simple access to a vast range of difluoromethyl derivatives of current interest to pharmaceutical, agrochemistry, and materials sciences. Using a catalytic frustrated Lewis pair approach, we have developed a generic protocol that allows a single substitution of one fluoride in trifluoromethyl groups with neutral phosphine and pyridine bases. The resulting phosphonium and pyridinium salts can be further functionalized via nucleophilic substitution, photoredox coupling, and electrophilic transfer reactions allowing the generation of a vast array of difluoromethyl products.

C-ARYL GLYCOSIDE COMPOUNDS FOR THE TREATMENT OF DIABETES AND OBESITY

This invention relates to a compound of generic formula (I): (I) as well as a pharmaceutically acceptable salt thereof, a tautomer, optical isomer or a mixture of optical isomers in any proportion, in particular a mixture of enantiomers, and particularly a racemate mixture, in particular for use thereof as a drug, notably in the treatment of diabetes.

Syntheses of New Aromatic Compounds with Fluorinated Side Chains and their Chemical Reactivity

The syntheses of a wide range of aromatic compounds of the type p-Y-C6H4CF2X(4-13) are described, and the chemical behavior of these compounds as a function of substituent Y is investigated .Analogously the pyridine derivatives 15, 17, and 18 were synthesized and characterized.From a correlation of the 19F-NMR data of these compounds with the Hammett constant of Y, participation of C-F ?-back-donation is seen as the cause for an observed shift of the 19F signals to lower field.