655-29-8

Upstream product

• 655-32-3 2,2,2-trifluoro-1-(4-fluorophenyl)ethanone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 1765-93-1 4-fluoroboronic acid 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 352-13-6 4-flourophenylmagnesium bromide 

Relevant academic research and scientific papers

One-pot synthesis of α-trifluoromethylstyrenes from aryl ketones and the Ruppert–Prakash reagent

A new synthesis of α-trifluoromethylstyrenes from aromatic ketones and (trifluoromethyl) trimethylsilane is described. The reaction involves nucleophilic trifluoromethylation and elimination of trimethylsilanol, which are performed within one reaction fla

Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF3-Substituted Tertiary Alcohol

Reported herein is a visible-light-induced sulfonation of α-trifluoromethylstyrenes with sodium sulfinates, which provides a series of α-trifluoromethyl-β-sulfonyl tertiary alcohols. This new synthetic protocol is enabled by a charge-transfer complex between oxygen and sulfinates, featuring broad substrate scope and scalability. Excellent functional group compatibility and chemoselectivity render this method suitable for sulfonation of pharmaceutically relevant molecules. In the presence of D2O, deuteriotrifluorinated products were also obtained, further demonstrating the flexibility and synthetic potentials of this strategy.

Electrochemical heterodifunctionalization of α-CF3alkenes to access α-trifluoromethyl-β-sulfonyl tertiary alcohols

An unprecedented electrochemical heterodifunctionalization of α-CF3alkenes with benzenesulfonyl hydrazides was accomplished in this work, wherein a β-sulfonyl and a α-hydroxyl group were simultaneously incorporated across the olefinic double bond in a single operation. Consequently, a series of potentially medicinally valuable and densely functionalized α-trifluoromethyl-β-sulfonyl tertiary alcohols were assembled under mild conditions. Electrochemically-driven oxidative 1,2-difunctionlization of electron-deficient alkenes well obviates the need for oxidizing reagents, thus rendering this protocol more eco-friendly.

Photoinduced Single-Electron Transfer as an Enabling Principle in the Radical Borylation of Alkenes with NHC–Borane

A photoinduced SET process enables the direct B?H bond activation of NHC–boranes. In contrast to common hydrogen atom transfer (HAT) strategies, this photoinduced reaction simply takes advantage of the beneficial redox potentials of NHC–boranes, thus obviating the need for extra radical initiators. The resulting NHC–boryl radical was used for the borylation of a wide range of α-trifluoromethylalkenes and alkenes with diverse electronic and structural features, providing facile access to highly functionalized borylated molecules. Labeling and photoquenching experiments provide insight into the mechanism of this photoinduced SET pathway.

The coupling of alkylboronic acids with α-(trifluoromethyl)styrenes by Lewis base/photoredox dual catalysis

Under Lewis base/photoredox dual catalysis, the defluorinative alkylation of alkylboronic acids with α-(trifluoromethyl)styrenes has been reported. In this system, both primary and secondary alkyl radicals produced by alkylboronic acids can react with α-(trifluoromethyl)styrenes to generate alkylated gem-difluoroalkenes. In general, the method has mild conditions, a wide substrate scope, and good functional group tolerance, which provides a new route for the synthesis of gem-difluoroalkenes.

Domino C-F Bond Activation of the CF3 Group: Synthesis of Fluorinated Dibenzo[a,c][7]annulenes from 2-(Trifluoromethyl)-1-alkenes and 2,2′-Diceriobiaryls

The construction of ring-fluorinated seven-membered carbocycles was readily achieved via the domino SN2′-type/SNV reaction between 2-(trifluoromethyl)-1-alkenes and 1,4-carbodianions. The SN2′-type reaction of 2-(trifluoromethyl)-1-alkenes with 2,2′-diceriobiaryls generated the intermediary 1,1-difluoro-1-alkenes bearing a monoceriobiaryl moiety, which in turn underwent intramolecular SNV reaction to afford fluorinated 5H-dibenzo[a,c][7]annulenes.

Photocatalytic alkene reduction by a B12-TiO2 hybrid catalyst coupled with C-F bond cleavage for: Gem -difluoroolefin synthesis

Photocatalytic syntheses of gem-difluoroolefins were performed using the B12-TiO2 hybrid catalyst during the CC bond reduction of α-trifluoromethyl styrenes with C-F bond cleavage at room temperature under nitrogen. The gem-difluoroolefins were used as synthetic precursors for fluorinated cyclopropanes.

Synthesis of α-trifluoromethylstyrene derivatives via Ni-catalyzed cross-coupling of 2-bromo-3,3,3-trifluoropropene and aryl Grignard reagents

The Ni-catalyzed cross-coupling of 2-bromo-3,3,3-trifluoropropene and aryl Grignard reagents was investigated. When NiCl2(PPh3)2 was used as a catalyst, the highest yield of α-trifluoromethylstyrene (89%) from 2-bromo-3,3,

Synthesis of gem-difluoroalkenes via β-fluoride elimination of organorhodium(I)

Treatment of α-(trifluoromethyl)styrenes with arylboronic esters and MeMgCl in the presence of a rhodium(I) catalyst affords gem-difluoroalkenes. The reaction proceeds through the addition of arylrhodium(I) species across the electron-deficient carbon-carbon double bond and the subsequent β-fluoride elimination. Copyright