13277-99-1

Upstream product

• 40662-66-6 <α,α-2H2>-4-methylbenzyl alcohol 
• 26204-18-2 <α,α,α-2H3>p-xylene 
• 94-08-6 4-methylbenzoic acid ethyl ester 
• 13463-40-6 iron pentacarbonyl 
• 624-31-7 4-tolyl iodide 
• 66343-78-0 <α-2H>-4-methylbenzyl alcohol 
• 589-18-4 4-Methylbenzyl alcohol 
• 104-82-5 4-Methylbenzyl chloride 
• 102677-60-1 1-(Benzenesulfonyl-methylsulfanyl-methyl)-4-methyl-benzene 
• 109635-31-6 C₁₅H₁₅⁽²⁾HO₂S₂ 

Downstream Products

• 4409-83-0 4-deuteriotoluene 
• 3160-38-1 (E)-4-p-tolylbut-3-en-2-one 
• 39994-24-6 phenyl(p-tolyl)methan-d₁-ol 
• 310903-46-9 (S)-(4-methylphenyl)-α-d-methanol 

Relevant academic research and scientific papers

Cu(II)-nitroxyl radicals as catalytic galactose oxidase mimics.

Results from Hammett correlation studies and primary kinetic isotope effects for the CuCl-TEMPO catalysed aerobic benzyl alcohol oxidations are inconsistent with an oxoammonium based mechanism. We postulate a copper-mediated dehydrogenation mechanism, in which TEMPO regenerates the active Cu(II)-species. This mechanism is analogous to that observed for Galactose Oxidase and mimics thereof.

Four-Component Radical Dual Difunctionalization (RDD) of Two Different Alkenes with Aldehydes and tert-Butyl Hydroperoxide (TBHP): An Easy Access to β,δ-Functionalized Ketones

A convenient Fe-catalyzed four-component radical dual difunctionalization and ordered assembly of two alkenes with aromatic/aliphatic aldehydes and TBHP to provide chain elongated β,δ-functionalized ketones via a one-pot procedure has been developed. Alde

Method for preparing deuterated aldehyde compound by using halomethyl compound as raw material

The invention provides a method for preparing deuterated aldehyde compound by using halomethyl compound as a raw material. The method comprises the following steps that in solvent and D2O mixed liquidwith a pyridine compound, the halomethyl compound is added; reaction is performed at 0 to 100 DEG C; then, a nitrosobenzene type compound is added for continuous reaction; finally, reaction liquid issubjected to acidification to obtain a target product. The method has the advantages that the used raw materials are cheap and can be easily obtained; expensive reagents or heavy metal raw materialsare not needed; the reaction conditions are simple; the severe conditions such as high temperature are not needed; the cost of the preparation method is low; the operation is simple; the deuterated rate is high and can reach 97 percent; the target product can be easily purified; the yield is high and reaches up to 95 percent. The substrates used by the method have wide applicability; various deuterated aldehyde compounds can be prepared.

One-Pot Synthesis of Deuterated Aldehydes from Arylmethyl Halides

A facile, one-pot approach for synthesizing deuterated aldehydes from arylmethyl halides was developed using D2O as the deuterium source. The efficient process is realized by a sequence of formation, H/D exchange, and oxidation of pyridinium salt intermediates. The mild and air-compatible reaction conditions enable efficient synthesis of diverse deuterated aldehydes with high deuterium incorporation.

Photocatalysis with Quantum Dots and Visible Light: Selective and Efficient Oxidation of Alcohols to Carbonyl Compounds through a Radical Relay Process in Water

Selective oxidation of alcohols to aldehydes/ketones has been achieved with the help of 3-mercaptopropionic acid (MPA)-capped CdSe quantum dot (MPA-CdSe QD) and visible light. Visible-light-prompted electron-transfer reaction initiates the oxidation. The thiyl radical generated from the thiolate anion adsorbed on a CdSe QD plays a key role by abstracting the hydrogen atom from the C?H bond of the alcohol (R1CH(OH)R2). The reaction shows high efficiency, good functional group tolerance, and high site-selectivity in polyhydroxy compounds. The generality and selectivity reported here offer a new opportunity for further applications of QDs in organic transformations.

Simple and Efficient Ruthenium-Catalyzed Oxidation of Primary Alcohols with Molecular Oxygen

Oxidative transformations utilizing molecular oxygen (O2) as the stoichiometric oxidant are of paramount importance in organic synthesis from ecological and economical perspectives. Alcohol oxidation reactions that employ O2are scarce in homogeneous catalysis and the efficacy of such systems has been constrained by limited substrate scope (most involve secondary alcohol oxidation) or practical factors, such as the need for an excess of base or an additive. Catalytic systems employing O2as the “primary” oxidant, in the absence of any additive, are rare. A solution to this longstanding issue is offered by the development of an efficient ruthenium-catalyzed oxidation protocol, which enables smooth oxidation of a wide variety of primary, as well as secondary benzylic, allylic, heterocyclic, and aliphatic, alcohols with molecular oxygen as the primary oxidant and without any base or hydrogen- or electron-transfer agents. Most importantly, a high degree of selectivity during alcohol oxidation has been predicted for complex settings. Preliminary mechanistic studies including18O labeling established the in situ formation of an oxo–ruthenium intermediate as the active catalytic species in the cycle and involvement of a two-electron hydride transfer in the rate-limiting step.

Palladium-catalysed reductive carbonylation of aryl halides with iron pentacarbonyl for synthesis of aromatic aldehydes and deuterated aldehydes

The first use of iron pentacarbonyl is described for the novel and efficient conversion of aryl iodides, bromides and chlorides into their corresponding aryl aldehydes and/or aryl deuterated aldehydes. The reaction is catalysed with Pd(0) in aqueous N,N-dimethylformamide at atmospheric pressure. In this protocol, neither gaseous hydrogen nor any reducing agent is required for the formation of the carbonylated product. The reaction can be performed without a P(III) ligand for aryl iodides; however, employing a P(III) ligand is necessary to perform the reaction with aryl bromides and chlorides.

A mild and highly efficient laccase-mediator system for aerobic oxidation of alcohols

With the aid of the highly active nitroxyl radical AZADO (2-azaadamantane N-oxyl), a simple method for the aerobic catalytic oxidation of alcohols is presented. The oxidations could typically proceed under practical ambient conditions (room temperature, air atmosphere, no moisture effect, metal-free, etc.) with a broad generality of the alcohol substrates, and especially for the oxidation of complex and highly functionalized alcohols. An ionic mechanism is proposed for the present system.

Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines

Isotopic labelling studies were performed to probe a proposed 1,2-aryl shift in the gold-catalysed cycloisomerisation of alkynyl aziridines into 2,4-disubstituted pyrroles. Two isotopomers of the expected skeletal rearrangement product were identified usi

Creation of highly stable monomeric Pd(II) species in an anion-exchangeable hydroxy double salt interlayer: Application to aerobic alcohol oxidation under an air atmosphere

An active Pd(II) catalyst supported on the Ni-Zn mixed basic salt (NiZn), which is classified by the anion-exchangeable layered hydroxy double salts, was synthesized by simple intercalation of the anionic Pd(II) hydroxyl complex. The divalent Pd species in the interlayer of NiZn maintained their original monomeric structure during the aerobic alcohol oxidation, due to the strong electrostatic interaction between the NiZn host and anionic Pd(II) species. This catalyst could be reused without any loss of the catalytic activity and selectivity in the aerobic alcohol oxidation.