136476-23-8

Upstream product

• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 149104-90-5 4-acetylphenylboronic acid 
• 99-90-1 para-bromoacetophenone 
• 13329-40-3 4-Iodoacetophenone 
• 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.

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.

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.