136476-23-8

Upstream product

• 99-90-1 para-bromoacetophenone 
• 13329-40-3 4-Iodoacetophenone 
• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 149104-90-5 4-acetylphenylboronic acid 
• 1601477-00-2 4-methyl-N'-(1,1,1-trifluoropropan-2-ylidene)benzenesulfonohydrazide 

Downstream Products

• 1638968-57-6 1-[4-(2-fluoro-3,4-dipropylcyclopenta-1,3-dien-1-yl)phenyl]ethan-1-one 
• 1638968-58-7 1-{4-[2-fluoro-3-methyl-4-(propan-2-yl)cyclopenta-1,3-dien-1-yl]phenyl}ethan-1-one 
• 1638968-59-8 1-(4-(2-fluoro-4-methyl-3-phenylcyclopenta-1,3-dienyl)phenyl)ethanone 
• 1638968-60-1 1-(4-(2-fluoro-3,4-diphenylcyclopenta-1,3-dienyl)phenyl)ethanone 
• 1638968-61-2 1-(4-(2-fluoro-3-(4-methoxyphenyl)-4-propylcyclopenta-1,3-dienyl)phenyl)ethanone 
• 1638968-72-5 C₄₇H₇₅F₃NiOP₂ 
• 1638968-74-7 1-(4-(1,1,1-trifluoropropan-2-yl)phenyl)ethanone 

Relevant academic research and scientific papers

Photoredox/Hydrogen Atom Transfer Cocatalyzed C-H Difluoroallylation of Amides, Ethers, and Alkyl Aldehydes

Herein, we report a method that combines hydrogen atom transfer and photoredox catalysis to achieve the dehydrogenative difluoroallylation of amides, ethers, and alkyl aldehydes. This operationally convenient method transforms a broad scope of substrates into the corresponding gem-difluoroalkenes via the construction of C(sp3)-C(sp3) or C(sp3)-C(sp2) bonds. Excellent functional group compatibility and high selectivity make this method have a wide range of substrate types and render it suitable for late-stage modification of pharmaceutical intermediates.

Photoredox relay-catalyzedgem-difluoroallylation of alkyl iodides

Herein, a new example of relay catalysis, using a combination of Mn2(CO)10and an iridium-based photocatalyst, is reported. In our relay catalytic reaction, the Mn catalyst and iridium-based photocatalyst catalyze the reaction at different stages in the desired sequence under the same reaction conditions, and do not inhibit each other. This convenient method transforms a broad scope of alkyl iodides into the correspondinggem-difluoroalkenesviaC(sp3)-C(sp3) bond construction. The protocol has good functional group tolerance and is suitable for the late-stage modification of multifunctional complex molecules.

Glycosyl-Radical-Based Synthesis of C-Alkyl Glycosides via Photomediated Defluorinative gem-Difluoroallylation

We have developed a stereoselective, glycosyl radical-based method for the synthesis of C-alkyl glycosides via a photomediated defluorinative gem-difluoroallylation reaction. We demonstrate for the first time that glycosyl radicals, generated from glycosyl bromides, can readily participate in a photomediated radical polar crossover process, affording a diverse array of gem-difluoroalkene containing C-glycosides. Notable features of this method include scalability, mild conditions, broad substrate scope, and suitability for the late-stage modification of complex molecules.

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

NiH-Catalyzed Migratory Defluorinative Olefin Cross-Coupling: Trifluoromethyl-Substituted Alkenes as Acceptor Olefins to Form gem-Difluoroalkenes

We report a NiH-catalyzed migratory defluorinative coupling between two electronically differentiated olefins. A broad range of unactivated donor olefins can be joined directly to acceptor olefins containing an electron-deficient trifluoromethyl substituent in both intra- and intermolecular fashion to form gem-difluoroalkenes. This migratory coupling shows both site- and chemoselectivity under mild conditions, with the formation of a tertiary or quaternary carbon center.

Flash generation and borylation of 1-(trifluoromethyl)vinyllithium toward synthesis of α-(trifluoromethyl)styrenes

Thermally unstable (3,3,3-trifluoroprop-1-en-2-yl)lithium was generated by lithiation of 2-bromo-3,3,3-trifluoroprop-1-ene and successively underwent borylation in a flow microreactor system. Direct use of the 1-(trifluoromethyl)vinylborate thus formed for the Suzuki–Miyaura coupling in a batch system afforded α-(trifluoromethyl)styrenes in high yields.

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.