87901-71-1

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 6185-76-8 (4-methoxyphenyl)(4-(trifluoromethyl)phenyl)methanone 
• 1443469-79-1 C₁₆H₁₅F₆NO₂ 
• 87901-56-2 C₁₅H₁₂F₃O⁽¹⁺⁾ 
• 5720-07-0 4-methoxyphenylboronic acid 
• 402-43-7 p-trifluoromethylphenyl bromide 

Downstream Products

• 120295-61-6 (4-trifluoromethyl-4'-methoxydiphenyl)methyl chloride 
• 41831-09-8 [1-(4-Methoxy-phenyl)-1-(4-trifluoromethyl-phenyl)-meth-(Z)-ylidene]-hydrazine 
• 1012862-97-3 methyl (4-methoxyphenyl)[4-(trifluoromethyl)phenyl]methyl carbonate 
• 429677-27-0 (4-trifluoromethylphenyl)-(4'-methoxyphenyl)methyl-α-d chloride 
• 429677-24-7 (4-trifluoromethyl-4'-methoxydiphenyl)methanol-α-D 
• 116669-35-3 (4-trifluoromethylphenyl)-(4'-methoxyphenyl)methyl 4-cyanophenyl ether 
• 915750-81-1 (Z)-1,1-dideuterio-3-(p-methoxyphenyl)-3-[(p-trifluoromethyl)phenyl]-2-methylprop-2-en-1-ol 

Relevant academic research and scientific papers

Light-driven MPV-type reduction of aryl ketones/aldehydes to alcohols with isopropanol under mild conditions

Alcohols are versatile structural motifs of pharmaceuticals, agrochemicals and fine chemicals. With respect to green chemistry, the development of more sustainable and cost-efficient processes for converting ketones/aldehydes to alcohols is highly desired. Herein, a direct light-driven strategy for reducing ketones/aldehydes to alcohols using isopropanol as the reducing agent and solvent, in the presence of t-BuOLi, under an air atmosphere at room temperature is developed. This operationally simple light-promoted Meerwein-Ponndorf-Verley (MPV) type reduction can be used to produce various benzylic alcohol derivatives as well as applied to bioactive molecules and PEEK model compounds, demonstrating its application potential.

Dirhodium-Catalyzed Enantioselective B?H Bond Insertion of gem-Diaryl Carbenes: Efficient Access to gem-Diarylmethine Boranes

The scarcity of reliable methods for synthesizing chiral gem-diarylmethine borons limits their applications. Herein, we report a method for highly enantioselective dirhodium-catalyzed B?H bond insertion reactions with diaryl diazomethanes as carbene precursors. These reactions afforded chiral gem-diarylmethine borane compounds in high yield (up to 99 % yield), high activity (turnover numbers up to 14 300), high enantioselectivity (up to 99 % ee) and showed unprecedented broad functional group tolerance. The borane compounds synthesized by this method could be efficiently transformed into diaryl methanol, diaryl methyl amine, and triaryl methane derivatives with good stereospecificity. Mechanistic studies suggested that the borane adduct coordinated to the rhodium catalyst and thus interfered with decomposition of the diazomethane, and that insertion of a rhodium carbene (generated from the diaryl diazomethane) into the B?H bond was most likely the rate-determining step.

Photocontrolled Radical Polymerization from Hydridic C-H Bonds

Given the ubiquity of carbon-hydrogen bonds in biomolecules and polymer backbones, the development of a photocontrolled polymerization selectively grafting from a C-H bond represents a powerful strategy for polymer conjugation. This approach would circumvent the need for complex synthetic pathways currently used to introduce functionality at a polymer chain end. On this basis, we developed a hydrogen-atom abstraction strategy that allows for a controlled polymerization selectively from a hydridic C-H bond using a benzophenone photocatalyst, a trithiocarbonate-derived disulfide, and visible light. We performed the polymerization from a variety of ethers, alkanes, unactivated C-H bonds, and alcohols. Our method lends itself to photocontrol which has important implications for building advanced macromolecular architectures. Finally, we demonstrate that we can graft polymer chains controllably from poly(ethylene glycol) showcasing the potential application of this method for controlled grafting from C-H bonds of commodity polymers.

An Efficient Ga(OTf)3/Isopropanol Catalytic System for Direct Reduction of Benzylic Alcohols

This study aims to report the first gallium-catalyzed direct reduction of benzylic alcohols using isopropanol as a reductant. The reaction proceeds via gallium catalyst-assisted hydride transfer of the in situ-generated benzylic isopropyl ether. The method generates only water and acetone as byproducts and thus provides an atom-economic and environmentally friendly approach to the synthesis of di- and triarylmethanes, which are important substructures in various bioactive compounds and functional materials. (Figure presented.).

Visible-Light-Triggered C-C and C-N Bond Formation by C-S Bond Cleavage of Benzylic Thioethers

The cleavage of sulfidic C-S bonds under visible-light irradiation was harnessed to generate carbocations under neutral conditions and synthesize valuable di- and triarylalkanes as well as benzyl amines. To this end, photoredox catalysis and direct photoinduced C-S bond cleavage are used as complementary approaches and participate in the versatility of the general strategy. Extensive mechanistic studies have demonstrated the diversity of the reaction mechanism at work in these different reactions.

Sp3 C-H Arylation and Alkylation Enabled by the Synergy of Triplet Excited Ketones and Nickel Catalysts

Triplet ketone sensitizers are of central importance within the realm of photochemical transformations. Although the radical-type character of triplet excited states of diaryl ketones suggests the viability for triggering hydrogen-atom transfer (HAT) and single-electron transfer (SET) processes, among others, their use as multifaceted catalysts in C-C bond-formation via sp3 C-H functionalization of alkane feedstocks still remains rather unexplored. Herein, we unlock a modular photochemical platform for forging C(sp3)-C(sp2) and C(sp3)-C(sp3) linkages from abundant alkane sp3 C-H bonds as functional handles using the synergy between nickel catalysts and simple, cheap and modular diaryl ketones. This method is distinguished by its wide scope that is obtained from cheap catalysts and starting precursors, thus complementing existing inner-sphere C-H functionalization protocols or recent photoredox scenarios based on iridium polypyridyl complexes. Additionally, such a platform provides a new strategy for streamlining the synthesis of complex molecules with high levels of predictable site-selectivity and preparative utility. Mechanistic experiments suggest that sp3 C-H abstraction occurs via HAT from the ketone triplet excited state. We believe this study will contribute to a more systematic utilization of triplet excited ketones as catalysts in metallaphotoredox scenarios.

Recyclable and reusable Pd(OAc)2/P(1-Nap)3/[bmim][PF6]/H2O system for the addition of arylboronic acids to aldehydes

A stable and efficient Pd(OAc)2/P(1-Nap)3[tri(1-naphthyl)phosphine] catalytic system for the addition of arylboronic acids to aldehydes has been developed. In the presence of Pd(OAc)2 and P(1-Nap)3, the addition reaction of arylboronic acids with aldehydes was carried out smoothly at 65 °C to give a variety of carbinol derivatives in good to excellent yields using a mixture of [bmim][PF6] and water as the solvent. The isolation of the products was readily performed by the extraction with diethyl ether, and the Pd(OAc)2/P(1-Nap)3/[bmim][PF6]/H2O system could be easily recycled and reused six times without significant loss of catalytic activity. Our system not only avoids the use of easily volatile THF or toluene as solvent but also solves the basic problem of palladium catalyst and these phosphine ligand reuse.

Sequential retro-ene arylation reaction of N-alkoxyenamides for the synthesis of tert -alkylamines

A sequential retro-ene arylation reaction has been developed for the conversion of N-alkoxyenamides to the corresponding tert-alkylamines in good yields via the nucleophilic addition of a triarylaluminum reagent to an in situ generated N-acylketimine. The reaction is tolerant of a range of functional groups and provides facile access to a series of tert-alkylamines that would be otherwise difficult to access using conventional procedures.

FeCl3-catalyzed 1,2-addition reactions of aryl aldehydes with arylboronic acids

(Chemical Equation Presented) A novel protocol for the 1,2-addition reactions of electron-deficient aryl aldehydes with arylboronic acids using an inexpensive and environmentally benign iron catalyst is reported. In the presence of FeCl3 and 2-

Stereoelectronic and solvent effects on the allylic oxyfunctionalization of alkenes with singlet oxygen

The factors that control the stereochemistry of sensitized photooxygenation of alkenes via singlet oxygen (ene reaction) are selectively reported. We also introduce our most recent stereoelectronic effects on the singlet oxygen-ene reaction. The origin of