4249-40-5

Upstream product

• 96-09-3 styrene oxide 
• 1121-70-6 sodium 4-methylphenoxide 
• 106-44-5 p-cresol 
• 70-11-1 α-bromoacetophenone 
• 14538-45-5 2-(4-methylphenoxy)acetophenone 
• 721-04-0 2-phenoxy-1-phenylethanone 
• 98-86-2 acetophenone 

Downstream Products

• 93-58-3 benzoic acid methyl ester 
• 106-44-5 p-cresol 
• 98-86-2 acetophenone 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Catalytic C–O bond cleavage in a β-O-4 lignin model through intermolecular hydrogen transfer

A base-free and redox neutral approach for the selective breaking of aryl ether bond (C–O) contained by a lignin model compound mimicking a β-O-4 linkage is reported. A palladium loaded metal-organic framework (MOF) was used as a catalyst for this purpose. The reaction proceeds through dehydrogenation of benzylic alcohol moiety followed by the hydrogenolysis of the ether bonds. Therefore, no external hydrogen source is required for the reaction to take place.

Cleavage∕cross-coupling strategy for converting β-O-4 linkage lignin model compounds into high valued benzyl amines via dual C–O bond cleavage

Lignin is the most recalcitrant of the three components of lignocellulosic biomass. The strength and stability of the linkages have long been a great challenge for the degradation and valorization of lignin biomass to obtain bio-fuels and commercial chemicals. Up to now, the selective cleavage of C–O linkages of lignin to afford chemicals contains only C, H and O atoms. Our group has developed a cleavage/cross-coupling strategy for converting 4-O-5 linkage lignin model compounds into high value-added compounds. Herein, we present a palladium-catalyzed cleavage/cross-coupling of the β-O-4 lignin model compounds with amines via dual C–O bond cleavage for the preparation of benzyl amine compounds and phenols.

Multiple Mechanisms Mapped in Aryl Alkyl Ether Cleavage via Aqueous Electrocatalytic Hydrogenation over Skeletal Nickel

We present here detailed mechanistic studies of electrocatalytic hydrogenation (ECH) in aqueous solution over skeletal nickel cathodes to probe the various paths of reductive catalytic C-O bond cleavage among functionalized aryl ethers relevant to energy science. Heterogeneous catalytic hydrogenolysis of aryl ethers is important both in hydrodeoxygenation of fossil fuels and in upgrading of lignin from biomass. The presence or absence of simple functionalities such as carbonyl, hydroxyl, methyl, or methoxyl groups is known to cause dramatic shifts in reactivity and cleavage selectivity between sp3 C-O and sp2 C-O bonds. Specifically, reported hydrogenolysis studies with Ni and other catalysts have hinted at different cleavage mechanisms for the C-O ether bonds in α-keto and α-hydroxy β-O-4 type aryl ether linkages of lignin. Our new rate, selectivity, and isotopic labeling results from ECH reactions confirm that these aryl ethers undergo C-O cleavage via distinct paths. For the simple 2-phenoxy-1-phenylethane or its alcohol congener, 2-phenoxy-1-phenylethanol, the benzylic site is activated via Ni C-H insertion, followed by beta elimination of the phenoxide leaving group. But in the case of the ketone, 2-phenoxyacetophenone, the polarized carbonyl πsystem apparently binds directly with the electron rich Ni cathode surface without breaking the aromaticity of the neighboring phenyl ring, leading to rapid cleavage. Substituent steric and electronic perturbations across a broad range of β-O-4 type ethers create a hierarchy of cleavage rates that supports these mechanistic ideas while offering guidance to allow rational design of the catalytic method. On the basis of the new insights, the usage of cosolvent acetone is shown to enable control of product selectivity.

Visible-light-induced C-C bond cleavage of lignin model compounds with cyanobenziodoxolone

The catalytic degradation of lignin to value-added chemicals has received considerable attention over the past decade. Photocatalysis provides promising approaches to enable previously inaccessible transformations. However, examples of the visible-light promoted degradation of lignin are still limited. In this work, the visible-light-induced selective C-C bond cleavage of β-O-4 lignin model compounds has been disclosed via β-scission of in situ generated alkoxy radical intermediates. With cyanobenziodoxolone as the oxidant, a variety of substrates could be transformed into aldehydes in moderate to good yields. In addition, unexpected acetal esters which could conveniently furnish formaldehyde and phenols by alcoholysis were observed.

Oxidative conversion of lignin and lignin model compounds catalyzed by CeO2-supported Pd nanoparticles

The oxidative transformation of lignin into aromatic compounds is an attractive route for chemical utilization of lignocellulosic biomass. Unlike hydrogenolysis, no consumption of expensive hydrogen is required for the oxidative transformation. However, only limited success has been achieved for the oxidative conversion of lignin. Here, we report that cerium oxide-supported palladium nanoparticles (Pd/ CeO2) can efficiently catalyze the one-pot oxidative conversion of 2-phenoxy-1-phenylethanol, a lignin model compound containing a β-O-4 bond and a Cα-hydroxyl group, in methanol in the presence of O2, producing phenol, acetophenone and methyl benzoate as the major products. Pd nanoparticles played a pivotal role in the oxidation of a Cα-hydroxyl group into a Cα-ketonic group, which was crucial for the transformation of the model compound. The presence of the Cα-ketonic group activated the β-O-4 bond, which was subsequently cleaved over the Pd/CeO2 catalyst, affording phenol and acetophenone. At the same time, the Cα-Cβ bond also underwent oxidative cleavage catalyzed by CeO2, producing benzoic acid and further methyl benzoate. The Pd/CeO2 catalyst could also catalyze the oxidative conversion of organosolv lignin under mild conditions (458 K), producing vanillin, guaiacol and 4-hydroxybenzaldehyde.

Novel hexafluoroisopropanol substituted ether derivatives

The invention is concerned with novel hexafluoroisopropanol substituted ether derivatives of formula (I): wherein R1 to R3 are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds bind to LXR alpha and LXR beta and can be used as medicaments.

Highly regioselective ring opening of epoxides with polymer supported phenoxide and naphthoxide anions

Amberlite IRA-400 supported phenoxide and naphthoxide anions are easily prepared. These polymer supported reagents that are highly air stable are used for the regioselective ring opening reactions of different epoxides to give aryl ether alcohols in high yields under mild reaction conditions.