155820-77-2

Upstream product

• 104-54-1 3-Phenylpropenol 
• 38126-07-7 difluorobromoacetyl fluoride 

Downstream Products

• 165074-27-1 bromodifluoroacetaldehyde cinnamyl O-(trimethylsilyl)acetal 
• 165074-24-8 (4-Benzyl-3,3-difluoro-tetrahydro-furan-2-yloxy)-trimethyl-silane 
• 17531-34-9 1-phenyl-3-trifluoromethyl prop-1-ene 
• 117969-61-6 cinnamyl fluoride 

Relevant academic research and scientific papers

BBDFA: A Practical Reagent for Trifluoromethylation of Allylic and Benzylic Alcohols on Preparative Scale

We report a safe and readily prepared reagent [1,1′-biphenyl]-4-yl 2-bromo-2,2-difluoroacetate (BBDFA) for Cu-catalyzed trifluoromethylation of allylic or benzylic alcohols. An operationally simple and column-chromatography-free process to prepare BBDFA was developed and demonstrated on >100 g scale. Detailed reaction calorimetry and thermal analysis of the deoxytrifluoromethylation were performed using cinnamyl alcohol as a model substrate, demonstrating that the reactions could be safely implemented on preparative scale.

Systematic synthesis of multifluorinated α,α-difluoro-γ-lactones through intramolecular radical cyclization

Carbon radicals from allyl O-(trimethylsilyl)-α-bromo-α,α- difluoroacetal can cyclize onto the olefinic part regiospecifically to give γ-lactols in good yield. The lactols are then converted to the corresponding α,α-difluoro-γ-lactones. Systematic synthesis of multifluorinated-α,α- difluoro-γ-lactones has thus been accomplished through intramolecular radical cyclization as a key reaction. Semiempirical MO calculation study suggested a unique nature of α,α-difluoroacetate in that complete delocalization of the electrons in the SOMO orbital of α,α-difluoroacetyl radical occurred; this caused unsuccessful cyclization. To apply the present radical reaction, the first synthesis of both enantiomers of difluoroeldanolide, analogues of the sex pheromone of the male African sugarcane borer, has been demonstrated. Electrophysiological tests revealed that the difluorinated analogues were as active as the natural eldanolide on the olfactory receptors.

Novel Synthesis of 2,2,2-Trifluoroethyl Compounds from Homoallylic Alcohols: A Copper(I) Iodide-initiated Trifluoromethyl-Dehydroxylation Process

Benzyl, prop-2-enyl and allyl chlorodifluoroacetates 3a, bromodifluoroacetates 3b or fluorosulfonyldifluoroacetates 3c, when decomposed in the presence of 1 equivalent of copper(I) iodide at an appropriate temperature in dimethylformamide, gave the corresponding trifluoromethyl derivatives in good to excellent yields.The products can also be obtained directly by ester exchange of XCF2CO2Et (X = FSO2, Cl, Br) 6 and the corresponding alcohols in the presence of KF and CuI.A trifluoromethylation-dehydroxylation mechanism, initiated by CuI, is proposed.