173974-87-3

Upstream product

• 109-06-8 α-picoline 
• 4377-33-7 2-chloromethylpyridine 
• 186581-53-3 diazomethane 
• 110-86-1 pyridine 
• 139032-23-8 1-isocyano-4-(trifluoromethyl)benzene 
• 368-48-9 2-(trifluoromethyl)pyridine 

Relevant academic research and scientific papers

Direct and Regioselective C(sp 3)-H Bond Fluorination of 2-Alkylazaarenes with Selectfluor

Herein, a regioselective and direct monofluorination strategy of pyridylic and quinolinic C(sp 3)-H bonds was developed under transition-metal-free conditions with Selectfluor. The reaction was performed under smooth conditions and afforded fluorinated azahetero cycles including 2-methylpyridines and -quinolines in moderate to good yields.

PROCESSES FOR FLUORINATION

The present technology relates to fluorination reactions. Specifically, processes useful for making the fungicide compound, DFT are disclosed. More broadly, also disclosed herein are processes useful for deoxyfluorination at the α-aromatic position of a given compound.

PROCESSES FOR FLUORINATION

The present technology relates to fluorination reactions. Specifically, processes useful for making the fungicide compound, DFT are disclosed. More broadly, also disclosed herein are processes useful for deoxyfluorination at the α-aromatic position of a given compound.

Selective C-F Functionalization of Unactivated Trifluoromethylarenes

Fluorinated organic molecules are pervasive within the pharmaceutical and agrochemical industries due to the range of structural and physicochemical properties that fluorine imparts. Currently, the most abundant methods for the synthesis of the aryl-CF2 functionality have relied on the deoxyfluorination of ketones and aldehydes using expensive and poorly atom economical reagents. Here, we report a general method for the synthesis of aryl-CF2R and aryl-CF2H compounds through activation of the corresponding trifluoromethyl arene precursors. This strategy is enabled by an endergonic electron transfer event that provides access to arene radical anions that lie outside of the catalyst reduction potential. Fragmentation of these reactive intermediates delivers difluorobenzylic radicals that can be intercepted by abundant alkene feedstocks or a hydrogen atom to provide a diverse array of difluoalkylaromatics.

Reaction of N-fluoropyridinium fluoride with isonitriles and diazo compounds: A one-pot synthesis of (pyridin-2-yl)-1H-1,2,3-triazoles

Reaction of N-fluoropyridinium fluoride generated in situ with a series of isonitriles and diazo compounds led to the formation of the corresponding (pyridine-2-yl)-1H-1,2,3-triazoles in good yields (37-59%). Best outcome was consistently achieved with bo

Conformational Preference of 2-(Halomethyl)- and 2-(Oxymethyl)pyridines: Microwave Spectrum, Ab Initio, and MM3 Studies of 2-(Fluoromethyl)pyridine

One single conformer was assigned from the microwave spectrum of 2-(fluoromethyl)pyridine, investigated in the gas phase in the 26.0-39.0 GHz spectral region at about -10 deg C.Its Cα-F bond was found to be coplanar with the ring and anti to the N-C2 bond (syn to the C2-C3 bond).There was no indication in the microwave spectrum of the presence of other rotameric forms of the molecule.The results of the spectroscopic study were backed up by ab initio calculations at the MP2/6-31 G** (frozen core) level.These calculations predict that the assigned conformer is the only stable form of the molecule.The transition state was calculated to have the CH2F group 180 deg from the stable anti conformation.The energy of the transition state was computed to be 20.2 kJ mol-1 higher than the energy of the anti rotamer.The results are interpreted in terms of a stereoelectronic effect, and the orbital overlaps responsible for the observed effect are discussed.It is shown that 2-(fluoromethyl)pyridine serves as a good model for 2-(alkoxymethyl)pyridines, previously found to show the same conformational preference. - Keywords: ab initio calculations; conformation; microwave spectroscopy; pyridines; stereoelectronic effect

N-Fluoro-bis[(trifluoromethyl)sulfonyl]imide: Electrophilic fluorination of imines and some methyl-substituted pyridines

Direct fluorination of imines with N-fluoro-bis[(trifluoromethyl)sulfonyl]imide 1 afforded mono and/or difluoroketones without the need of a strong base to first generate the imine anions. Structurally related 2- and 4-methyl-substituted pyridines gave the respective fluoromethyl pyridines with 1. Our results suggest that an enamine intermediate plays a key role in these reactions.