74552-54-8

Upstream product

• 121985-99-7 2-hydroxy-2-(2-methoxyphenyl)acetonitrile 
• 100-52-7 benzaldehyde 
• 135-02-4 ortho-anisaldehyde 
• 613-90-1 benzoyl cyanide 
• 31675-43-1 diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate 
• 34082-43-4 2-methoxybenzil 
• 13278-00-7 2-methoxybenzaldehyde-α-d₁ 
• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 1333394-50-5 (2-methoxyphenyl)(2-phenyl-1,3-dithian-2-yl)methanol 
• 74552-51-5 Diethyl 2-hydroxy-2-(2-methoxyphenyl)-1-(trimethylsiloxy)-1-phenylethanephosphonate 
• 82128-71-0 2-(2-methyloxyphenyl)-2-(trimethylsilyloxy)acetonitrile 

Downstream Products

• 73867-38-6 2-acetoxy-1-phenyl-2-(2-methoxyphenyl)ethanone 
• 1333394-67-4 (S)-1-(2-methoxyphenyl)-2-oxo-2-phenylethyl butyrate 
• 100-52-7 benzaldehyde 
• 135-02-4 ortho-anisaldehyde 
• 24534-42-7 4-methoxy-2-phenylbenzofuran 
• 34082-43-4 2-methoxybenzil 

Relevant academic research and scientific papers

Rate and equilibrium constants for the addition of N-heterocyclic carbenes into benzaldehydes: A remarkable 2-substituent effect

Abstract Rate and equilibrium constants for the reaction between N-aryl triazolium N-heterocyclic carbene (NHC) precatalysts and substituted benzaldehyde derivatives to form 3-(hydroxybenzyl)azolium adducts under both catalytic and stoichiometric conditions have been measured. Kinetic analysis and reaction profile fitting of both the forward and reverse reactions, plus onwards reaction to the Breslow intermediate, demonstrate the remarkable effect of the benzaldehyde 2-substituent in these reactions and provide insight into the chemoselectivity of cross-benzoin reactions. It takes 2-: Measurement of rate and equilibrium constants for the reaction between N-aryl triazolium NHC precatalysts and substituted benzaldehydes under catalytic and stoichiometric conditions demonstrate the remarkable kinetic and thermodynamic effect of the benzaldehyde 2-substituent in these reactions, potentially providing insight into the chemoselectivity of cross-benzoin reactions.

Selective Metal-Free Deoxygenation of Unsymmetrical 1,2-Dicarbonyl Compounds by Chlorotrimethylsilane and Sodium Iodide

For the first time, the combination of chlorotrimethylsilane with NaI is used as a selective reducting system toward 1,2-diketones. This combination is successfully evaluated with several unsymmetrically benzil derivatives, which are reduced in good yield

Chemoenzymatic synthesis of chiral unsymmetrical benzoin esters

A chemoenzymatic Dynamic Kinetic Resolution (DKR) of unsymmetrical benzoins (Ar1≠Ar2) has been carried out, by using Pseudomonas stutzeri lipase stereorecognition pattern. After studying this lipase behaviour, a high preference towards acylation of those benzoins containing substituents in the phenyl ring rather than in the benzoyl moiety was observed. This fact allowed the development of the DKR process of this kind of substrates, avoiding the accumulation of secondary products derived from the in situ racemization mediated by Shvo's catalyst action, and allowing the synthesis of enantiopure unsymmetrical benzoins acetates (not previously described) in very good yields (60-95%) and excellent enantiomeric excess values (always >99%).

A family of thiazolium salt derived N-heterocyclic carbenes (NHCs) for organocatalysis: Synthesis, investigation and application in cross-benzoin condensation

A family of thiazolium salt derived N-heterocyclic carbenes (NHCs) bearing sterically demanding aryl substituents on the nitrogen and with varying backbone substitution patterns have been synthesized. Investigation of the catalytic activity of these NHCs in a number of benzoin-type coupling reactions revealed markedly different levels of reactivity and selectivity. To elucidate the underlying factors leading to differences in reactivity, a study of the electronic and steric properties of these NHC catalysts was conducted. By using the best catalyst in this study, the intermolecular cross-benzoin condensation reaction was explored in more detail.

Lewis acid-promoted friedel-crafts alkylation reactions with α-ketophosphate electrophiles

The BF3·OEt2-promoted nucleophilic substitution of α-aryl-α-ketophosphates to afford α,α-diaryl ketone products is described. Electron-rich α-ketophosphates perform best, with electron-neutral and electron-poor substrates also tolerated. The reaction is tolerant of a range of aromatic, heteroaromatic, and nonaromatic nucleophiles, with yields ranging from 44% to 84%. Enantioenriched starting material yields racemic product, suggesting an SN1 pathway via an acylcarbenium ion.

Photoremovable Protecting Groups for Phosphorylation of Chiral Alcohols. Asymmetric Synthesis of Phosphotriesters of (-)-3',5'-Dimethoxybenzoin

Procedures have been developed for the preparation of dimethoxybenzoinyl (DMB) phosphate triesters that can be deprotected photochemically.These compounds can be useful in light-directed synthesis and caging.The photochemistry of a wide variety of fluorine-, oxygen-, and nitrogen-substituted benzoin acetates was examined to determine the substitution pattern in the nonacylated aromatic ring producing optimum chemical yields.Two groups, 2',3'-dimethoxybenzoin and 3',5'-dimethoxybenzoin, were found to give the highest yields of the benzofuran product and were further developed for the photochemical deprotection of phosphate esters.These reactions could not be quenched, suggesting a singlet photosolvolysis mechanism.An asymmetric synthesis of 3',5'-dimethoxybenzoin via the benzaldehyde cyanohydrin was developed that minimizes the number of diastereomers formed in the phosphorylation of chiral alcohols.A phosphoramidite reagent for the derivatization of alcohols was prepared and used to produce scalemic dimethoxybenzoinyl phosphate esters from pantolactone and glycerol, serine, and tyrosine derivatives.These compounds were deprotected photochemically to produce the phosphodiesters in high yield.

Reductive Coupling of Benzoyl Cyanide and Carbonyl Compounds by Aqueous Ti(III) Ions. A New Convenient and Selective Access to the Less Stable Mixed Benzoins

The reactive species formed by the Ti(III) ion reduction of benzoyl cyanide (1) adds to the C-atom of carbonyl compounds 2 under simple experimental conditions.The intermediate 1,2-diols 3 are smoothly converted, without isolation, into the less thermodynamically stable mixed benzoins 4, which are not accessible by the classical benzoin condensation.The possible mechanisms involved in the reaction are discussed.

α-HETEROSUBSTITUTED PHOSPHONATE CARBANIONS IX : DIETHYL 1-PHENYL-1-TRIMETHYLSILOXYMETHANE PHOSPHONATE AS AN ACYL ANION EQUIVALENT; A NOVEL METHOD FOR THE PREPARATION OF α-HYDROXYKETONES.

Diethyl 1-phenyl-1-trimethylsiloxymethane phosphonate carbanion was found to react as an effective acyl anion equivalent in the preparation of α-hydroxy ketones from aliphatic and aromatic aldehydes and ketones.A 1,4-oxygen-oxygen silicon migration was also observed.

α-Heterosubstituted Phosphonate Carbanions. 11. Benzoins via an Acyl Anion Equivalent. Novel One-Pot Preparation of Benzofurans via Benzoins Using Hydriodic Acid

Diethyl 1-(trimethylsiloxy)-1-phenylmethanephosphonate carbanion 2 is introduced as a novel acyl anion equivalent.When 2 reacts with aldehydes or ketones, a 1,4 oxygen-oxygen silicon migration with subsequent loss of diethyl lithium phosphite is observed.An efficient method utilizing 2 for the preparation of otherwise difficultly obtainable substituted benzoins is presented.Also a novel one-pot method which offers a facile entry into the 2-phenylbenzofuran ring system from 2 via benzoin intermediates using hydriodic acid was developed.