Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Solvent-Dependent Facile Synthesis of Diaryl Selenides and Biphenols Employing Selenium Dioxide.

ABSTRACT: Biphenols are important structure motifs for ligand systems in organic catalysis and are therefore included in the category of so-called "privileged ligands". We have developed a new synthetic pathway to construct these structures by the use of selenium dioxide, a stable, powerful, and commercially available oxidizer. Our new, and easy to perform protocol gives rise to biphenols and diaryl selenides depending on the solvent employed. Oxidative treatment of phenols in acetic acid yields the corresponding biphenols, whereas conversion in pyridine results in the preferred formation of diaryl selenides. As a consequence, we were able to isolate a broad scope of novel diaryl selenides, which could act as pincer-like ligands with further applications in organic synthesis or as ligands in transition metal catalysis.

SUBMITTER: Quell T

PROVIDER: S-EPMC4906476 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Solvent-Dependent Facile Synthesis of Diaryl Selenides and Biphenols Employing Selenium Dioxide.

Quell Thomas T Mirion Michael M Schollmeyer Dieter D Dyballa Katrin M KM Franke Robert R Waldvogel Siegfried R SR

ChemistryOpen 20151211 2

Biphenols are important structure motifs for ligand systems in organic catalysis and are therefore included in the category of so-called "privileged ligands". We have developed a new synthetic pathway to construct these structures by the use of selenium dioxide, a stable, powerful, and commercially available oxidizer. Our new, and easy to perform protocol gives rise to biphenols and diaryl selenides depending on the solvent employed. Oxidative treatment of phenols in acetic acid yields the corre ...[more]

PMID: 27308222

Similar Datasets

Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides.

Project description:A novel method of photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides has been developed. Although the arylation reactions with triarylbismuthines are usually catalyzed by transition-metal complexes, the present arylation of diaryl diselenides with triarylbismuthines proceeds upon photoirradiation in the absence of transition-metal catalysts. A variety of unsymmetrical diaryl selenides can be conveniently prepared by using this arylation method.

| S-EPMC3701414 | biostudies-literature

Palladium-catalyzed three-component diaryl sulfone synthesis exploiting the sulfur dioxide surrogate DABSO.

Project description: Not available

| S-EPMC4138993 | biostudies-literature

Iodine-Mediated Oxidative Rearrangement of α,β-Unsaturated Diaryl Ketones: A Facile Access to 1,2-Diaryl Diketones.

Project description:A metal-free oxidative rearrangement was explored for the synthesis of 1,2-diaryl diketones by utilizing α,β-unsaturated diaryl ketones and I2/TBHP in good to high yields. The reaction proceeds via oxidative aryl migration, followed by C-C bond cleavage. A simple and high-yielding protocol was developed for the synthesis of a wide range of 1,2-diaryl diketones, which are the backbone for a variety of medicinally important molecules.

| S-EPMC6648810 | biostudies-literature

Synthesis of novel alkynyl imidazopyridinyl selenides: copper-catalyzed tandem selenation of selenium with 2-arylimidazo[1,2-<i>a</i>]pyridines and terminal alkynes.

Project description:Alkynyl selenides have attracted considerable research interest recently, owing to their applications in the biological and pharmaceutical fields. The Cu-catalyzed tandem reaction for the synthesis of novel alkynyl imidazopyridinyl selenides is presented. A one-pot synthesis route afforded alkynyl imidazopyridinyl selenides in moderate to good yields. This was achieved by a two-step reaction between terminal alkynes and diimidazopyridinyl diselenides, generated from imidazo[1,2-a]pyridines and Se powder, using 10 mol % of CuI and 1,10-phenanthroline as the catalytic system under aerobic conditions. The C(sp2)-Se and C(sp)-Se bond-formation reaction can be performed in one-pot by using inexpensive and easy to handle Se powder as the Se source. The reaction proceeded with terminal alkynes having various substitutions, such as aryl, vinyl, and alkyl groups. The obtained alkynyl imidazopyridinyl selenide was found to undergo nucleophilic substitution reaction on Se atom using organolithium reagents and 1,3-dipolar azide-alkyne cycloaddition based on the alkyne moiety.

| S-EPMC9344556 | biostudies-literature

Facile Solvent-Free Synthesis of Metal Thiophosphates and Their Examination as Hydrogen Evolution Electrocatalysts.

Project description:The facile solvent-free synthesis of several known metal thiophosphates was accomplished by a chemical exchange reaction between anhydrous metal chlorides and elemental phosphorus with sulfur, or combinations of phosphorus with molecular P2S5 at moderate 500 °C temperatures. The crystalline products obtained from this synthetic approach include MPS3 (M = Fe, Co, Ni) and Cu3PS4. The successful reactions benefit from thermochemically favorable PCl3 elimination. This solvent-free route performed at moderate temperatures leads to mixed anion products with complex heteroatomic anions, such as P2S64-. The MPS3 phases are thermally metastable relative to the thermodynamically preferred separate MPx/ MSy and more metal-rich MPxSy phases. The micrometer-sized M-P-S products exhibit room-temperature optical and magnetic properties consistent with isolated metal ion structural arrangements and semiconducting band gaps. The MPS3 materials were examined as electrocatalysts in hydrogen evolution reactions (HER) under acidic conditions. In terms of HER activity at lower applied potentials, the MPS3 materials show the trend of Co > Ni >> Fe. Extended time constant potential HER experiments show reasonable HER stability of ionic and semiconducting MPS3 (M = Co, Ni) structures under acidic reducing conditions.

| S-EPMC9413033 | biostudies-literature

Facile Synthesis of Enzyme-Embedded Metal-Organic Frameworks for Size-Selective Biocatalysis in Organic Solvent.

Project description:In situ immobilization of enzyme into metal-organic frameworks (MOFs) is performed through a one-step and facile method. Candida antarctica lipase B (CalB) is directly embedded in zeolitic imidazolate framework (ZIF)-8 by simply mixing an aqueous solution of 2-methylimidazole and zinc nitrate hexahydrate [Zn(NO3)2?6H2O] containing CalB at room temperature. Due to the intrinsic micropores of ZIF-8, the obtained CalB@ZIF composite is successfully applied in size-selective transesterification reaction in organic solvent. CalB@ZIF not only shows much higher catalytic activity but also exhibits higher thermal stability than free CalB. Besides, the robust ZIF-8 shell also offers the hybrid composites excellent reusability.

| S-EPMC7358279 | biostudies-literature

Facile synthesis of symmetrical bis(benzhydryl)ethers using p-toluenesulfonyl chloride under solvent-free conditions.

Project description:BackgroundThe benzhydryl ether moiety is widely distributed in nature and constitutes a key structural motif in numerous molecules of significant biological potential and of prospective clinical uses. Solvent-free and cost-effective facile synthesis of symmetrical bis(benzhydryl)ethers is, thus, much desirable.ResultsA simple and efficient method for the facile synthesis of symmetrical bis(benzhydryl)ethers directly from the corresponding benzhydrols has been developed using a catalytic amount of p-toluenesulfonyl chloride (5 mol%) at an oil bath temperature of 110°C under solvent-free conditions.ConclusionsOperational simplicity, low reagent loading, high product yields, short reaction time, and solvent-free conditions are the notable advantages of the present method.

| S-EPMC3637510 | biostudies-literature

Quaternary Selenides EuLnCuSe3: Synthesis, Structures, Properties and In Silico Studies.

Project description:In this work, we report on the synthesis, in-depth crystal structure studies as well as optical and magnetic properties of newly synthesized heterometallic quaternary selenides of the Eu+2Ln+3Cu+1Se3 composition. Crystal structures of the obtained compounds were refined by the derivative difference minimization (DDM) method from the powder X-ray diffraction data. The structures are found to belong to orthorhombic space groups Pnma (structure type Ba2MnS3 for EuLaCuSe3 and structure type Eu2CuS3 for EuLnCuSe3, where Ln = Sm, Gd, Tb, Dy, Ho and Y) and Cmcm (structure type KZrCuS3 for EuLnCuSe3, where Ln = Tm, Yb and Lu). Space groups Pnma and Cmcm were delimited based on the tolerance factor t', and vibrational spectroscopy additionally confirmed the formation of three structural types. With a decrease in the ionic radius of Ln3+ in the reported structures, the distortion of the (LnCuSe3) layers decreases, and a gradual formation of the more symmetric structure occurs in the sequence Ba2MnS3 → Eu2CuS3 → KZrCuS3. According to magnetic studies, compounds EuLnCuSe3 (Ln = Tb, Dy, Ho and Tm) each exhibit ferrimagnetic properties with transition temperatures ranging from 4.7 to 6.3 K. A negative magnetization effect is observed for compound EuHoCuSe3 at temperatures below 4.8 K. The magnetic properties of the discussed selenides and isostructural sulfides were compared. The direct optical band gaps for EuLnCuSe3, subtracted from the corresponding diffuse reflectance spectra, were found to be 1.87-2.09 eV. Deviation between experimental and calculated band gaps is ascribed to lower d states of Eu2+ in the crystal field of EuLnCuSe3, while anomalous narrowing of the band gap of EuYbCuSe3 is explained by the low-lying charge-transfer state. Ab initio calculations of the crystal structures, elastic properties and phonon spectra of the reported compounds were performed.

| S-EPMC8836063 | biostudies-literature

Supercritical carbon dioxide: a solvent like no other.

Project description:Supercritical carbon dioxide (scCO2) could be one aspect of a significant and necessary movement towards green chemistry, being a potential replacement for volatile organic compounds (VOCs). Unfortunately, carbon dioxide has a notoriously poor solubilising power and is famously difficult to handle. This review examines attempts and breakthroughs in enhancing the physicochemical properties of carbon dioxide, focusing primarily on factors that impact solubility of polar and ionic species and attempts to enhance scCO2 viscosity.

| S-EPMC4168859 | biostudies-literature

Synthesis and evaluation of diaryl sulfides and diaryl selenide compounds for antitubulin and cytotoxic activity.

Project description:We have devised a procedure for the synthesis of analogs of combretastatin A-4 (CA-4) containing sulfur and selenium atoms as spacer groups between the aromatic rings. CA-4 is well known for its potent activity as an inhibitor of tubulin polymerization, and its prodrugs combretastatin A-4 phosphate (CA-4P) and combretastatin A-1 phosphate (CA-1P) are being investigated as antitumor agents that cause tumor vascular collapse in addition to their activity as cytotoxic compounds. Here we report the preparation of two sulfur analogs and one selenium analog of CA-4. All synthesized compounds, as well as several synthetic intermediates, were evaluated for inhibition of tubulin polymerization and for cytotoxic activity in human cancer cells. Compounds 3 and 4 were active at nM concentration against MCF-7 breast cancer cells. As inhibitors of tubulin polymerization, both 3 and 4 were more active than CA-4 itself. In addition, 4 was the most active of these agents against 786, HT-29 and PC-3 cancer cells. Molecular modeling binding studies are also reported for compounds 1, 3, 4 and CA-4 to tubulin within the colchicine site.

| S-EPMC3774136 | 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