471856-97-0

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 1601477-00-2 4-methyl-N'-(1,1,1-trifluoropropan-2-ylidene)benzenesulfonohydrazide 
• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 126747-14-6 4-cyanophenylboronic acid 
• 357274-85-2 α-(trifluoromethyl)ethenyl boronic acid 
• 23516-85-0 4-(2,2,2-trifluoroacetyl)benzonitrile 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 2730-62-3 2-chloro-1,1,1-trifluoropropene 

Downstream Products

• 1079398-15-4 C₁₆H₁₁F₂N 
• 1638968-62-3 4-(2-fluoro-3,4-dipropylcyclopenta-1,3-dienyl)benzonitrile 
• 1620096-76-5 4-(1,1-difluoroprop-1-en-2-yl)benzonitrile 

Relevant academic research and scientific papers

Remote Regioselective Radical C-H Functionalization of Unactivated C-H Bonds in Amides: The Synthesis of gem-Difluoroalkenes

The site-selective functionalization of unactivated aliphatic amines is an attractive and challenging synthetic approach. We herein report a general strategy for the remote site-selective functionalization of unactivated C(sp3)-H bonds in amides by photogenerated amidyl radicals to form gem-difluoroalkenes with trifluoromethyl-substituted alkenes. The site selectivity is controlled by a 1,5-hydrogen atom transfer (HAT) process of the amide. This photocatalyzed transformation shows both chemo- and site-selectivity, facilitating the formation of a secondary, tertiary, or quaternary carbon center.

Photoredox-Catalyzed Difunctionalization of Unactivated Olefins for Synthesizing Lactam-Substituted gem-Difluoroalkenes

Herein, the synthesis of lactam-substituted gem-difluoroalkenes has been developed through a photoredox-catalyzed radical cascade reaction. This developed photoredox-catalyzed, Br?nsted base-assisted intramolecular 5-exo-trig cyclization/intermolecular radical addition/β-fluoride elimination reaction offers a simple method for producing lactam, carbamate, or urea-substituted gem-difluoroalkenes with good functional group tolerance and high yields.

Catalyzing the Hydrodefluorination of CF3-Substituted Alkenes by PhSiH3. H?Transfer from a Nickel Hydride

The hydrodefluorination of CF3-substituted alkenes can be catalyzed by a nickel(II) hydride bearing a pincer ligand. The catalyst loading can be as low as 1 mol%. gem-Difluoroalkenes containing a number of functional groups can be formed in goo

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.

Synthesis ofgem-difluoroalkenesvianickel-catalyzed allylic defluorinative reductive cross-coupling of trifluoromethyl alkenes with epoxides

A nickel-catalyzed defluorinative reductive cross-coupling of trifluoromethyl alkenes with epoxides has been developed. Various substituted trifluoromethyl alkenes and epoxides were found to be suitable reaction substrates. This reaction enabled C(sp

Visible-Light-Induced Radical Defluoroborylation of Trifluoromethyl Alkenes: An Access to gem-Difluoroallylboranes

A photoredox-catalyzed defluoroborylation of trifluoromethyl alkenes with N-heterocyclic carbene boranes is described for the synthesis of gem-difluoroallylboranes. This protocol exhibits a broad substrate scope and good functional group compatibility, which enables the late-stage functionalization of structurally complex compounds. Further transformations of the defluoroborylation products to valuable CF2-containing molecules are also demonstrated. (Figure presented.).

Palladium-catalyzed Suzuki–Miyaura reaction of fluorinated vinyl chloride: a new approach for synthesis α and α,β-trifluoromethylstyrenes

A mild and efficient palladium-catalyzed cross-coupling between fluorinated vinyl chloride and arylboronic acids is described. The use of ligand B successfully overcomes the strong electronic withdrawing of trifluoromethylated substrates and allows the efficient synthesis of a wide range of α and α,β-trifluoromethyl containing olefins. By using this method, the key intermediate for synthesis of Efavirenz can be obtained in a simple route. The efficient conversion of two freon molecules into useful α and α,β-trifluoromethyl containing olefins is a useful route in organic chemistry.

Double C-F bond activation through β-fluorine elimination: Nickel-mediated [3+2] cycloaddition of 2-trifluoromethyl-1-alkenes with alkynes

The nickel-mediated [3+2] cycloaddition of 2-trifluoromethyl-1-alkenes with alkynes afforded fluorine-containing multi-substituted cyclopentadienes in a regioselective manner. This reaction involves the consecutive two C-F bond cleavage of a trifluoromethyl or a pentafluoroethyl group through β-fluorine elimination.

A general synthesis of α-trifluoromethylstyrenes through palladium-catalyzed cross-couplings with 1,1,1-trifluoroacetone tosylhydrazone

1,1,1-Trifluoroacetone tosylhydrazone is presented as a very convenient substrate for the palladium-catalyzed cross-coupling with aryl halides. Under the proper reaction conditions, 3,3,3-trifluoromethylstyrenes - very valuable trifluoromethylated synthetic intermediates - are obtained with high yields. The reaction features a very wide scope, as the presence of most functional groups is tolerated. Moreover, the reaction has been extended to substituted trifluoromethylstyrenes by employing substituted tosylhydrazones derived from other trifluoromethyl ketones.

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