50562-10-2

Upstream product

• 106-38-7 para-bromotoluene 
• 148992-43-2 1-ethoxy-2,2-difluoroethanol 
• 704-36-9 2,2-difluoro-1-(4-methylphenyl)ethan-1-one 
• 104-87-0 4-methyl-benzaldehyde 
• 58310-28-4 (Difluoromethyl)triphenylphosphonium bromide 
• 65864-64-4 trimethyl(difluoromethyl)silane 
• 122590-88-9 2,2-difluoro-1-(4-methylphenyl)-2-phenylsulfonylethanol 

Downstream Products

• 50562-11-3 Toluene-4-sulfonic acid 2,2-difluoro-1-p-tolyl-ethyl ester 
• 704-36-9 2,2-difluoro-1-(4-methylphenyl)ethan-1-one 
• 50561-97-2 1-(2,2-difluoroethyl)-4-methylbenzene 

Relevant academic research and scientific papers

Visible light-promoted umpolung coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines

Tertiary alcohols bearing a trifluoromethyl group are of considerable medicinal interest. Using an umpolung strategy, we herein report the first intermolecular reductive cross-coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines with the aid of a Br?nsted acid catalyst upon visible-light irradiation. This metal-free reaction is operationally simple and performed at ambient temperature, allowing access to desired tertiary alcohols with tri-/difluoromethyl groups in moderate to excellent yields. The commercially available and easily handled Hantzsch ester effectively serves as an electron donor, as well as a hydrogen atom source.

Direct Nucleophilic Difluoromethylation of Carbonyl Compounds

Phosphonium salt ([Ph3P+CF2H] Br-, DFPB) was found to be an efficient nucleophilic difluoromethylation reagent. Although DFPB is known as a phosphonium ylide precursor, its reaction with carbonyl compounds under traditional Wittig reaction conditions did not give the expected Wittig difluoroolefinated products, but afforded the nucleophilic difluoromethylation products, α-CF2H alcohols. Mechanistic investigation reveals that the unexpected transformation proceeded via the direct transfer of the CF2H group, which resulted from the high P-O affinity.

Difluromethylphosphonium salt, and preparation method and application thereof

The invention discloses difluromethylphosphonium salt, and a preparation method and application thereof. A synthetic method of the difluromethylphosphonium salt disclosed by the invention comprises the following steps of in a solvent, carrying out a react

Organocatalytic direct difluoromethylation of aldehydes and ketones with TMSCF2H

An organic Lewis base promoted direct difluoromethylation reaction of carbonyl compounds with Me3SiCF2H has been studied. The Schwesinger's superbase can efficiently activate the Si-CF2H bond and initiate the difluoromethy

Toward a Unified Mechanism for Oxoammonium Salt-Mediated Oxidation Reactions: A Theoretical and Experimental Study Using a Hydride Transfer Model

A range of oxoammonium salt-based oxidation reactions have been explored computationally using density functional theory (DFT), and the results have been correlated with experimentally derived trends in reactivity. Mechanistically, most reactions involve a formal hydride transfer from an activated C-H bond to the oxygen atom of the oxoammonium cation. Several new potential modes of reactivity have been uncovered and validated experimentally.

A Remarkably Simple Route to Versatile Difluoromethylated Molecules

Difluoroacetaldehyde ethyl hemiacetal (1), prepared from ethyl difluoroacetate and lithium aluminum hydride in diethyl ether, was found to be a potential difluoroethylating reagent for the preparation of a wide variety of difluoromethylated compounds.Compound 1 shows promise for use in the synthesis of carbinols prepared by the reaction of 1 with metal reagents or enol silyl ethers, the synthesis of amino acid ketones and β-lactams via the nucleophilic reaction of imines, and the synthesis of sugar analogues.

Process for nucleophilic fluoroalkylation of aldehydes

Aryl difluoromethyl sulfone adds to alkehydes under phase transfer conditions to give novel substituted alcohols of the general formula wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.

NUCLEOPHILIC ADDITION OF DIFLUOROMETHYL PHENYL SULFONE TO ALDEHYDES AND VARIOUS TRANSFORMATIONS OF THE RESULTING ALCOHOLS

Nucleophilic addition of difluoromethyl phenyl sulfone (1) to various aldehydes occured in a two phase system ( 50 percent aqueous sodium hydroxide, dichloromathane, Aliquat 336 ) to give difluoro(phenylsulfonyl)methyl substituted alcohols (2-8).The product alcohol derived from para-tolualdehyde was converted to the difluoromethylated alcohol by desulfonylation and to the α, β, β-trifluorostyrene by a fluorination-elimination sequence.In the absence of aldehydes, 1 reacted in two phase system to give difluoro(phenylsulfonyl)methyl phenyl sulfide (9).The pathway of the latter conversion was studied.