Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Transesterification of (hetero)aryl esters with phenols by an Earth-abundant metal catalyst.

ABSTRACT: Readily available and inexpensive Earth-abundant alkali metal species are used as efficient catalysts for the transesterification of aryl or heteroaryl esters with phenols which is a challenging and underdeveloped transformation. The simple conditions and the use of heterogeneous alkali metal catalyst make this protocol very environmentally friendly and practical. This reaction fills in the missing part in transesterification reaction of phenols and provides an efficient approach to aryl esters, which are widely used in the synthetic and pharmaceutical industry.

SUBMITTER: Chen J

PROVIDER: S-EPMC9082394 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Transesterification of (hetero)aryl esters with phenols by an Earth-abundant metal catalyst.

Chen Jianxia J Namila E E Bai Chaolumen C Baiyin Menghe M Agula Bao B Bao Yong-Sheng YS

RSC advances 20180713 44

Readily available and inexpensive Earth-abundant alkali metal species are used as efficient catalysts for the transesterification of aryl or heteroaryl esters with phenols which is a challenging and underdeveloped transformation. The simple conditions and the use of heterogeneous alkali metal catalyst make this protocol very environmentally friendly and practical. This reaction fills in the missing part in transesterification reaction of phenols and provides an efficient approach to aryl esters, ...[more]

PMID: 35542121

Similar Datasets

General and selective deoxygenation by hydrogen using a reusable earth-abundant metal catalyst.

Project description:Chemoselective deoxygenation by hydrogen is particularly challenging but crucial for an efficient late-stage modification of functionality-laden fine chemicals, natural products, or pharmaceuticals and the economic upgrading of biomass-derived molecules into fuels and chemicals. We report here on a reusable earth-abundant metal catalyst that permits highly chemoselective deoxygenation using inexpensive hydrogen gas. Primary, secondary, and tertiary alcohols as well as alkyl and aryl ketones and aldehydes can be selectively deoxygenated, even when part of complex natural products, pharmaceuticals, or biomass-derived platform molecules. The catalyst tolerates many functional groups including hydrogenation-sensitive examples. It is efficient, easy to handle, and conveniently synthesized from a specific bimetallic coordination compound and commercially available charcoal. Selective, sustainable, and cost-efficient deoxygenation under industrially viable conditions seems feasible.

| S-EPMC6858257 | biostudies-literature

Copper-Mediated Radiobromination of (Hetero)Aryl Boronic Pinacol Esters.

Project description:A copper-mediated radiobromination of (hetero)aryl boronic pinacol esters is described. Cyclotron-produced [76/77Br]bromide was isolated using an anion exchange cartridge, wherein the pre-equilibration and elution solutions played a critical role in downstream deboro-bromination. The bromination tolerates a broad range of functional groups, labeling molecules with ranging electronic and steric effects. Bologically active radiopharmaceuticals were synthesized, including two radiobrominated inhibitors of poly ADP ribose polymerase, a clinically relevant chemotherapeutic target for ovarian, breast, and prostate cancers.

| S-EPMC9957949 | biostudies-literature

Palladium-Catalyzed Decarbonylative Coupling of (Hetero)Aryl Boronate Esters with Difluorobenzyl Glutarimides.

Project description:This report describes the Pd-catalyzed decarbonylative coupling of difluorobenzyl glutarimides with (hetero)aryl boronate esters to yield difluorobenzyl-substituted (hetero)arene products. The use of PAd2Bu as the phosphine ligand in combination with neopentylboronate ester nucleophiles proved critical for the selective formation of the decarbonylative coupling product versus analogous difluorobenzyl ketone. This transformation is effective for electronically diverse (hetero)aryl boronate esters and substituted difluorobenzyl glutarimides.

| S-EPMC10629228 | biostudies-literature

Chemoselective single-site Earth-abundant metal catalysts at metal-organic framework nodes.

Project description:Earth-abundant metal catalysts are critically needed for sustainable chemical synthesis. Here we report a simple, cheap and effective strategy of producing novel earth-abundant metal catalysts at metal-organic framework (MOF) nodes for broad-scope organic transformations. The straightforward metalation of MOF secondary building units (SBUs) with cobalt and iron salts affords highly active and reusable single-site solid catalysts for a range of organic reactions, including chemoselective borylation, silylation and amination of benzylic C-H bonds, as well as hydrogenation and hydroboration of alkenes and ketones. Our structural, spectroscopic and kinetic studies suggest that chemoselective organic transformations occur on site-isolated, electron-deficient and coordinatively unsaturated metal centres at the SBUs via σ-bond metathesis pathways and as a result of the steric environment around the catalytic site. MOFs thus provide a novel platform for the development of highly active and affordable base metal catalysts for the sustainable synthesis of fine chemicals.

| S-EPMC5013626 | biostudies-literature

Photochemically-Mediated, Nickel-Catalyzed Synthesis of <i>N</i>-(Hetero)aryl Sulfamate Esters.

Project description:A general method is described for the coupling of (hetero)aryl bromides with O-alkyl sulfamate esters. The protocol relies on catalytic amounts of nickel and photoexcitable iridium complexes and proceeds under visible light irradiation at ambient temperature. This technology engages a broad range of simple and complex O-alkyl sulfamate ester substrates under mild conditions. Furthermore, it is possible to avoid undesirable N-alkylation, which was found to plague palladium-based protocols for N-arylation of O-alkyl sulfamate esters. These investigations represent the first use of sulfamate esters as nucleophiles in transition metal-catalyzed C-N coupling processes.

| S-EPMC7241445 | biostudies-literature

4-Dimethylaminopyridine-Catalyzed Metal-Free Aerobic Oxidation of Aryl α-Halo Esters to Aryl α-Keto Esters.

Project description:A novel, metal-free aerobic oxidation method is described. 4-Dimethylaminopyridine (DMAP) successfully catalyzed the oxidation of aryl α-halo esters to corresponding aryl α-keto esters (up to 95% yield) under mild reaction conditions (Li2CO3, dimethylacetamide, air, and room temperature). A mechanism has been proposed where the oxidation proceeds through a [3 + 2] cycloaddition between O2 in an air atmosphere and pyridinium ylides. The ylides are supposedly generated from aryl α-halo esters and DMAP in the presence of carbonates. Based on the plausible mechanism, the potential of DMAP as a catalyst in oxidation reactions was extended.

| S-EPMC7495759 | biostudies-literature

Atmospheric- and Low-Level Methane Abatement <i>via</i> an Earth-Abundant Catalyst.

Project description:Climate action scenarios that limit changes in global temperature to less than 1.5 °C require methane controls, yet there are no abatement technologies effective for the treatment of low-level methane. Here, we describe the use of a biomimetic copper zeolite capable of converting atmospheric- and low-level methane at relatively low temperatures (e.g., 200-300 °C) in simulated air. Depending on the duty cycle, 40%, over 60%, or complete conversion could be achieved (via a two-step process at 450 °C activation and 200 °C reaction or a short and long activation under isothermal 310 °C conditions, respectively). Improved performance at longer activation was attributed to active site evolution, as determined by X-ray diffraction. The conversion rate increased over a range of methane concentrations (0.00019-2%), indicating the potential to abate methane from any sub-flammable stream. Finally, the uncompromised catalyst turnover for 300 h in simulated air illustrates the promise of using low-cost, earth-abundant materials to mitigate methane and slow the pace of climate change.

| S-EPMC10114903 | biostudies-literature

An improved catalyst system for the Pd-catalyzed fluorination of (hetero)aryl triflates.

Project description:The stable Pd(0) species [(1,5-cyclooctadiene)(L·Pd)2] (L = AdBrettPhos) has been prepared and successfully evaluated as a precatalyst for the fluorination of aryl triflates derived from biologically active and heteroaryl phenols, challenging substrates for our previously reported catalyst system. Additionally, this precatalyst activates at room temperature under neutral conditions, generates 1,5-cyclooctadiene as the only byproduct, and leads to overall cleaner reaction profiles.

| S-EPMC3858322 | biostudies-literature

Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce-Smiles Rearrangement.

Project description:A new benzyne transformation is described that affords versatile biaryl structures without recourse to transition-metal catalysis or stoichiometric amounts of organometallic building blocks. Aryl sulfonamides add to benzyne upon fluoride activation, and then undergo an aryl Truce-Smiles rearrangement to afford biaryls with sulfur dioxide extrusion. The reaction proceeds under simple reaction conditions and has excellent scope for the synthesis of sterically hindered atropisomeric biaryl amines.

| S-EPMC4819888 | biostudies-literature

Metal-organic layers stabilize earth-abundant metal-terpyridine diradical complexes for catalytic C-H activation.

Project description:We report the synthesis of a terpyridine-based metal-organic layer (TPY-MOL) and its metalation with CoCl2 and FeBr2 to afford CoCl2·TPY-MOL and FeBr2·TPY-MOL, respectively. Upon activation with NaEt3BH, CoCl2·TPY-MOL catalyzed benzylic C-H borylation of methylarenes whereas FeBr2·TPY-MOL catalyzed intramolecular Csp3 -H amination of alkyl azides to afford pyrrolidines and piperidines. X-ray absorption near edge structure (XANES), extended X-ray absorption fine structure (EXAFS), X-ray photoelectron spectroscopy, UV-Vis-NIR spectroscopy, and electron paramagnetic spectroscopy (EPR) measurements as well as density functional theory (DFT) calculations identified M(THF)2·TPY-MOL (M = Co or Fe) as the active catalyst with a MII-(TPY˙˙)2- electronic structure featuring divalent metals and TPY diradical dianions. We believe that site isolation stabilizes novel MII-(TPY˙˙)2- (M = Co or Fe) species in the MOLs to endow them with unique and enhanced catalytic activities for Csp3 -H borylation and intramolecular amination over their homogeneous counterparts. The MOL catalysts are also superior to their metal-organic framework analogs owing to the removal of diffusion barriers. Our work highlights the potential of MOLs as a novel 2D molecular material platform for designing single-site solid catalysts without diffusional constraints.

| S-EPMC5869321 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data