38935-94-3

Upstream product

• 83567-75-3 diethyl 2-(4-(dimethylamino)phenyl)-1,1-difluoro-2-phenylethylphosphonate 
• 1219454-89-3 2-((difluoromethyl)sulfonyl)pyridine 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 87189-16-0 potassium 2-bromo-2,2-difluoroacetate 
• 1895-39-2 sodium chlorodifluoroacetate 
• 94993-99-4 diethyl difluoromethylphosphonate lithium salt 
• 75-61-6 dibromodifluoromethane 

Downstream Products

• 1350433-03-2 1-dimethylamino-4-(2,2,2-trifluoroethyl)benzene 
• 1350432-96-0 C₁₀H₁₂F₂⁽¹⁸⁾FN 
• 1450719-47-7 4-(cyclopentylidenemethyl)-N,N-dimethylaniline 

Relevant academic research and scientific papers

A useful magnesium reagent for the preparation of 1,1-difluoro-2-hydroxyphosphonates from diethyl bromodifluoromethylphosphonate via a metal-halogen exchange reaction

When (EtO)2P(O)CF2Br (1) is treated with isopropylmagnesium chloride in THF at low temperature it gives a magnesium species (2) which undergoes reactions with strong electrophiles (HCl, TMSCl, halogens, aldehydes and ketones). The formation of products depends strongly on the reaction conditions. With 1.5 equivalents of 2 between - 78 and 0°C, a conversion of more than 90% of aldehydes and ketones into 2-hydroxyphosphonates (7 and 8) can be achieved. These compounds (7 and 8) in the presence of base (NaH, LDA) are rearranged into 2,2-difluoroethylphosphates without concomitant formation of 1,1-difluoroolefines.

Organocatalytic strategy for hydrophenolation of gem-difluoroalkenes

Gem-difluoroalkenes are an easily accessed fluorinated functional group, and a useful intermediate for elaborating into more complex fluorinated compounds. Currently, most functionalization reactions of gem-difluoroalkenes, with or without a transition metal-based catalyst system, involve the addition or removal of a fluorine atom to generate trifluorinated or monofluorinated products, respectively. In contrast, we present a complementary “fluorine-retentive” reaction that exploits an organocatalytic strategy to add phenols across gem-difluoroalkenes to deliver β,β-difluorophenethyl arylethers. The products are produced in good to moderate yields and selectivities, thus providing a range of compounds that are underrepresented in the synthetic and medicinal chemistry literature.

Base Catalysis Enables Access to α,α-Difluoroalkylthioethers

A nucleophilic addition reaction of aryl thiols to readily available β,β-difluorostyrenes provides α,α-difluoroalkylthioethers. The reaction proceeds through an unstable anionic intermediate, prone to eliminate fluoride and generate α-fluorovinylthioethers. However, the use of base catalysis overcomes the facile β-fluoride elimination, generating α,α-difluoroalkylthioethers in excellent yields and selectivities.

Copper-Catalyzed Regioselective Monodefluoroborylation of Polyfluoroalkenes en Route to Diverse Fluoroalkenes

Monodefluoroborylation of polyfluoroalkenes has been achieved in a regioselective manner under mild conditions via copper catalysis. The method has shown an extremely broad scope of substrates, including (difluorovinyl)arenes, tetrafluoroethylene (TFE), (

Direct Difluoromethylenation of Carbonyl Compounds by Using TMSCF3: The Right Conditions

A deoxygenative difluoromethylenation of carbonyl compounds has been developed by using readily available, inexpensive trifluoromethyltrimethylsilane, LiI, and PPh3. The presence of the Li+ion prevents the unproductive exhaustion of trifluoromethyltrimethylsilane (TMSCF3) by keeping the soluble free fluoride concentration in the reaction medium under control. The strategy of combining solvents to increase the reactivity and thereby reduce the reaction temperature and time is disclosed.

Synthesis and decarboxylative Wittig reaction of difluoromethylene phosphobetaine

A key intermediate, difluoromethylene phosphobetaine, in the Wittig reaction of ClCF2CO2Na-Ph3P with aldehydes was synthesized and characterized, which confirmed the reaction mechanism. The decarboxylation of this stable intermediate was a convenient approach for Wittig difluroolefination. Its reactivity could be adjusted by the modification of the substituent on the phosphorus.

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.

Difluoromethyl 2-pyridyl sulfone: A new gem-difluoroolefination reagent for aldehydes and ketones

Chemical equation presented Difluoromethyl 2-pyridyl sulfone, a previously unknown compound, was found to act as a novel and efficient gem-difluoroolefination reagent for both aldehydes and ketones. It was found that the fluorinated sulfinate intermediate in the reaction is relatively stable, which can be observed by 19F NMR and trapped with CH 3l.

(DIETHYLPHOSPHINYL)DIFLUOROMETHYLLITHIUM. -PREPARATION AND SYNTHETIC APPLICATION-

The action of lithium diisopropylamide on diethyl difluoromethylphosphonate gives the title reagent which reacts with various electrophiles to introduce difluoromethylene or difluoromethyl unit.

An investigation into the origins of polar substituent effects upon 19F chemical shifts, using 4-substituted β,β-difluorostyrenes

19F, 13C, and 1H chemical shifts have been determined for β,β-difluorostyrene and eight 4-substituted derivatives.The β-fluorine chemical shift difference, ΔδF, is used to evaluate the constant in the Buckingham equation.A=3.0*10-11