881682-92-4

Usage

Family

Fluoroalkyl ketone

Usage

a. Organic synthesis
b. Medicinal chemistry

Physical state

Yellow liquid at room temperature

Odor

Strong

Function

a. Reagent in the preparation of various organic compounds
b. Used in the pharmaceutical industry for the synthesis of potential drug candidates

Unique property

Presence of fluorine atoms in the molecule

Value

Valuable building block for the development of novel chemical and pharmaceutical substances

Upstream product

• 881682-70-8 benzyl α,β,β-trifluoroacrylate 
• 2622-05-1 allylmagnesium bromide 

Relevant academic research and scientific papers

Preparation and addition-elimination reactions of benzyl α,β,β-trifluoroacrylate. A new stereoselective approach to (Z)-β-substituted α,β-difluoroacrylates

(Chemical Equation Presented) Benzyl α,β,β- trifluoroacrylate (1) was prepared in good yield via the reductive Br-F elimination of benzyl 2-bromo-2,3,3,3-tetrafluoropropanoate or the palladium-catalyzed cross-coupling reaction of 1,2,2-trifluorovinylstannane with benzyl chloroformate. On treating 1 with various Grignard reagents or dialkylzinc reagents in the presence of copper(I) salt, the corresponding β-substituted α,β-difluoroacrylates were obtained in high yields with high Z-selectivity. Additionally, trialkylaluminum reagents were also found to be good nucleophiles, the corresponding addition-elimination products being afforded in good yields but with low stereoselectivity.

Novel synthesis of (Z)-difluoroacrylates via a highly stereoselective addition-elimination reaction

On treating readily prepared benzyl 2,3,3-trifluoroacrylate with various Grignard reagents, e.g., aryl-, alkyl-, or alkenylmagnesium halide, in the presence of a catalytic amount of copper(I) salt in THF at -78 °C for 1 h, the corresponding α,β-difluoroacrylates were obtained in 54-98% yields with high Z-selectivity.