178180-81-9

Upstream product

• 55186-75-9 4-trifluoromethyl-α-methylstyrene 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 1774-47-6 trimethylsulfoxonium iodide 
• 2252-62-2 2-(4-(trifluoromethyl)phenyl)propan-2-ol 
• 75-11-6 diiodomethane 

Downstream Products

• 869319-00-6 2-(4-(trifluoromethyl)phenyl)prop-2-en-1-ol 
• 103108-04-9 2-(α,α,α-trifluoro-p-tolyl)propanal 
• 284686-92-6 2-(α,α,α-trifluoro-p-tolyl)propan-1-ol 
• 500019-42-1 (S)-β-methyl-4-trifluoromethylbenzeneethanol 
• 134904-86-2 2-Methyl-2-(4-trifluoromethylphenyl)acetic acid 

Relevant academic research and scientific papers

Radical-mediated aerobic oxidation of substituted styrenes and stilbenes

A 2,2-azobis(isobutyronitrile)-catalyzed oxidative cleavage of alkenes with molecular oxygen as the oxidant was described. Carbonyl compounds and oxiranes were obtained in moderate yield under mild conditions. This study provided useful insights into the mechanism of aerobic oxidative cleavage of alkenes.

Biocatalytic Parallel Interconnected Dynamic Asymmetric Disproportionation of α-Substituted Aldehydes: Atom-Efficient Access to Enantiopure (S)-Profens and Profenols

The biocatalytic asymmetric disproportionation of aldehydes catalyzed by horse liver alcohol dehydrogenase (HLADH) was assessed in detail on a series of racemic 2-arylpropanals. Statistical optimization by means of design of experiments (DoE) allowed the identification of critical interdependencies between several reaction parameters and revealed a specific experimental window for reaching an ′optimal compromise′ in the reaction outcome. The biocatalytic system could be applied to a variety of 2-arylpropanals and granted access in a redox-neutral manner to enantioenriched (S)-profens and profenols following a parallel interconnected dynamic asymmetric transformation (PIDAT). The reaction can be performed in aqueous buffer at ambient conditions, does not rely on a sacrificial co-substrate, and requires only catalytic amounts of cofactor and a single enzyme. The high atom-efficiency was exemplified by the conversion of 75 mM of rac-2-phenylpropanal with 0.03 mol% of HLADH in the presence of ～0.013 eq. of oxidized nicotinamide adenine dinucleotide (NAD+), yielding 28.1 mM of (S)-2-phenylpropanol in 96% ee and 26.5 mM of (S)-2-phenylpropionic acid in 89% ee, in 73% overall conversion. Isolated yield of 62% was obtained on 100 mg-scale, with intact enantiopurities. (Figure presented.).

An air-stable cationic iridium hydride as a highly active and general catalyst for the isomerization of terminal epoxides

We describe the use of an air-stable iridium hydride catalyst for the isomerization of terminal epoxides into aldehydes with perfect regioselectivity. The system operates at low loadings of catalyst (0.5 mol%), is highly practical, scalable, and tolerates functional groups that would not be compatible with Lewis acids typically used in stoichiometric amounts. Evidence for a rare hydride mechanism are provided. This journal is the Partner Organisations 2014.

Synthesis of quaternary carbon centers via hydroformylation

The application of hydroformylation to the synthesis of quaternary carbon centers is reported. The synthesis of the highly substituted carbon is achieved by applying a catalytic amount of 1. Ligand 1 serves as a catalytic directing group by covalently and reversibly binding to both the substrate and catalyst. The intramolecular nature of the directing group strategy accelerates the hydroformylation reaction such that the reaction is performed at mild temperatures (35-55 °C) and with excellent regioselectivity (b:l > 94:6).

Enzymatic transformations 63. High-concentration two liquid-liquid phase Aspergillus niger Epoxide hydrolase-catalysed resolution: Application to trifluoromethyl-substituted aromatic epoxides

The aim of this work was to perform different studies allowing us to improve the methodology we had previously described to realise the Aspergillus niger epoxide hydrolase-catalysed resolution of eight trifluoromethyl- substituted styrene oxide derivative

Reactivity and selectivity in the oxidation of styrene derivatives, II studies on the oxidation of p-substituted α-methylstyrenes

The liquid phase oxidation of p-substituted (Br-, Cl-, t-Bu-, MeO-, CF3-) α-methylstyrenes and of α,p-dimethoxystyrene with pure oxygen was investigated in chlorobenzene solution and in presence of cumene and of cumene hydroperoxide in the temperature range 65-125°C. The product yields were determined gaschromatographically. The differences of the activation energies of the epoxide formation and the parallel reactions amount to 19-48 kJ/mol. The epoxide selectivity increases with increasing temperature and concentration of olefine. The relative chain propagation constants kp (C=C) were determined by competitive oxidation with cumene. The kp(C=C) values of p-substituted α-methylstyrenes can be correlated by the Hammett equation with both σ and σ+ substituent constants.