119352-47-5

Upstream product

• 100-52-7 benzaldehyde 
• 141334-29-4 1,1-difluoro-2-triphenylsilyloxypropene 
• 676-58-4 methylmagnesium chloride 
• 1015236-35-7 3-(benzyloxy)-2,2-difluoro-1-phenylbut-3-en-1-ol 
• 210348-33-7 2,2-difluoro-1-phenyl-3-(phenylthio)but-3-en-1-ol 
• 88257-33-4 1-chloro-1,1-difluoroacetone monohydrate 

Downstream Products

• 1268827-17-3 (Z)-ethyl 4,4-difluoro-5-hydroxy-3-methyl-5-phenylpent-2-enoate 
• 1268830-41-6 C₁₂H₁₂F₂O₃ 
• 1268826-99-8 5,5-difluoro-4-methyl-6-phenyl-5,6-dihydro-2H-pyran-2-one 
• 1268826-85-2 (Z)-methyl 4,4-difluoro-5-hydroxy-3-methyl-5-phenylpent-2-enoate 
• 1268826-98-7 (Z)-ethyl 5-(tert-butyldimethylsilyloxy)-4,4-difluoro-3-methyl-5-phenylpent-2-enoate 
• 1268826-84-1 (Z)-methyl 5-(tert-butyldimethylsilyloxy)-4,4-difluoro-3-methyl-5-phenylpent-2-enoate 
• 1268826-82-9 4-(tert-butyldimethylsilyloxy)-3,3-difluoro-4-phenylbutan-2-one 

Relevant academic research and scientific papers

α,α-Difluoro-α-(trimethylsilyl)acetamides as Versatile Reagents for the Preparation of Difluorinated Aldol and Mannich Adducts

The very efficient addition of α,α-difluoro-α-(trimethylsilyl)acetamides to aldehydes, ketones and N-(tert-butanesulfinyl)imines is described. The reaction is promoted by a catalytic amount of tetra-n-butylammonium diphenyltrifluorosilicate (TBAT) and high yields, as well as very high stereoselectivities in the case of N-(tert-butanesulfinyl)imines, are achieved. The synthetic potential of this method is illustrated by the conversion of the resulting products to β-hydroxy ketones, diols and β-amino alcohols by addition of various Grignard reagents or reduction of the amide moiety. (Figure presented.).

Brook/Elimination/Aldol Reaction Sequence for the Direct One-Pot Preparation of Difluorinated Aldols from (Trifluoromethyl)trimethylsilane and Acylsilanes

A methodology allowing the one-pot preparation of difluorinated aldols directly from Ruppert-Prakash reagent, acyltrimethylsilanes and aldehydes is reported. The process, initiated by a catalytic amount of an ammonium salt, involves the addition of (trifluoromethyl)trimethylsilane to the acylsilane, followed by a Brook rearrangement and elimination of a fluoride anion that promotes the subsequent aldol reaction. An efficient racemic reaction catalyzed by tetrabutylammonium difluorotriphenylsilicate is described, as well as our first efforts towards an asymmetric version.

Gem-difluorinated homoallyl alcohols, β-hydroxy ketones, and syn- and anti-1, 3-diols via γ,γ-difiuoroallylboronates

γ,γ-Difluoroallylboronates have been prepared from trifluoroethanol and utilized for the allylboration of a variety of aldehydes to provide gem-difluorinated homoallylic alcohols. α-Chiral aldehydes were allylborated in 4:1-13:1 diastereoselectivity favoring the anti-isomer. A representative series of difluorinated hydroxyl enol ethers were converted to the corresponding α, α-difluoro-β-hydroxy ketones. Diastereoselective reduction of one of these to either syn- and anti-1,3-diol was also studied.

Allylation of novel β-phenylthio substituted gem-difluoroallylic bromide to carbonyl compounds

The reaction of β-phenylthio substituted gem-difluoroallylic bromide 3 with aldehydes and ketones in the presence of Zn(Cu) in THF at reflux temperature afforded the corresponding homoallylic alcohols 4 in good yields.

TRIFLUOROACETYLTRIPHENYLSILANE AS A POTENTIALLY USEFUL FLUORINE-CONTAINING BUILDING BLOCK. PREPARATION AND ITS TRANSFORMATION INTO 2,2-DIFLUORO ENOL SILYL ETHERS

The first example of perfluoroacylsilanes - trifluoroacetyltriphenylsilane was prepared in good yield and it has been converted into a series of 2,2-difluoro enol silyl ethers in almost quantitative yields by treatment with various organolithiums.

FLUORINE-CONTAINING ORGANOZINC REAGENTS. IV. REFORMATSKII-TYPE REACTIONS OF CHLORODIFLUOROACETIC ACID DERIVATIVES

Chlorodifluoroacetic acid has shown to be a promising starting material for Reformatskii-type syntheses of fluorine-containing molecules and thus, it offers an attractive extension to what is known from rather expensive bromodifluoroacetic acid.