Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Visible-light-induced bromoetherification of alkenols for the synthesis of ?-bromotetrahydrofurans and -tetrahydropyrans.

ABSTRACT: A visible-light-induced photoredox-catalyzed bromoetherification of alkenols is described. This approach, with CBr4 as the bromine source through generation of bromine in situ, provides a mild and operationally simple access to the synthesis of ?-bromotetrahydrofurans and -tetrahydropyrans with high efficiency and regioselectivity.

SUBMITTER: Lin R

PROVIDER: S-EPMC4311724 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Visible-light-induced bromoetherification of alkenols for the synthesis of β-bromotetrahydrofurans and -tetrahydropyrans.

Lin Run R Sun Hongnan H Yang Chao C Yang Youdong Y Zhao Xinxin X Xia Wujiong W

Beilstein journal of organic chemistry 20150108

A visible-light-induced photoredox-catalyzed bromoetherification of alkenols is described. This approach, with CBr4 as the bromine source through generation of bromine in situ, provides a mild and operationally simple access to the synthesis of β-bromotetrahydrofurans and -tetrahydropyrans with high efficiency and regioselectivity. ...[more]

PMID: 25670989

Similar Datasets

Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues.

Project description:Tetrahydropyrans are abundantly found in marine natural products. The interesting biological properties of these compounds and their analogues make necessary the development of convenient procedures for their synthesis. In this paper, an atom economy access to tetrahydropyrans by intramolecular acid-mediated cyclization of silylated alkenols is described. p-TsOH has shown to be an efficient reagent to yield highly substituted tetrahydropyrans. Moreover, excellent diastereoselectivities are obtained both for unsubstituted and alkylsubstituted vinylsilyl alcohols. The methodology herein developed may potentially be applied to the synthesis of marine drugs derivatives.

| S-EPMC6265778 | biostudies-literature

Direct visible-light-induced synthesis of P-stereogenic phosphine oxides under air conditions.

Project description:Over the past two decades, visible-light-induced transformations have been regarded as being among the most environmentally benign and powerful strategies for constructing complex molecules and diverse synthetic building blocks in organic synthesis. However, the development of efficient photochemical processes for assembling enantiomerically pure molecules remains a significant challenge. Herein, we describe a simple and efficient visible-light-induced C-P bond forming reaction for the synthesis of P-chiral heteroaryl phosphine oxides in moderate to high yields with excellent ee values (97-99% ee). Even in the absence of transition metal or photoredox catalysts, a variety of P-chiral heteroaryl phosphine oxides, including chiral diphosphine oxide 41, have been directly obtained under air conditions. Density functional theory (DFT) calculations have shown that the reaction involves intersystem crossing and single electron transfer to give a diradical intermediate under visible light irradiation.

| S-EPMC9172294 | biostudies-literature

Solar synthesis: prospects in visible light photocatalysis.

Project description:Chemists have long aspired to synthesize molecules the way that plants do-using sunlight to facilitate the construction of complex molecular architectures. Nevertheless, the use of visible light in photochemical synthesis is fundamentally challenging because organic molecules tend not to interact with the wavelengths of visible light that are most strongly emitted in the solar spectrum. Recent research has begun to leverage the ability of visible light-absorbing transition metal complexes to catalyze a broad range of synthetically valuable reactions. In this review, we highlight how an understanding of the mechanisms of photocatalytic activation available to these transition metal complexes, and of the general reactivity patterns of the intermediates accessible via visible light photocatalysis, has accelerated the development of this diverse suite of reactions.

| S-EPMC4547527 | biostudies-literature

Synthesis of (±)-Tetrabenazine by Visible Light Photoredox Catalysis.

Project description:(±)-Tetrabenazine was synthesized in six steps from commercially available compounds. The key cyclization substrate was assembled rapidly via Baylis-Hillman and aza-Michael reactions. Annulation of the final ring was achieved through visible light photocatalysis, wherein carbon-carbon bond formation was driven by the oxidation of a tertiary amine. Solvent played a critical role in the photoredox cyclization outcome, whereas methanol led to a mixed ketal, acetonitrile/water (10:1) gave direct cyclization to (±)-tetrabenazine and occurred more rapidly.

| S-EPMC4684717 | biostudies-literature

Intracellular Synthesis of Indoles Enabled by Visible-Light Photocatalysis.

Project description:Performing abiotic synthetic transformations in live cell environments represents a new, promising approach to interrogate and manipulate biology and to uncover new types of biomedical tools. We now found that photocatalytic bond-forming reactions can be added to the toolbox of bioorthogonal synthetic chemistry. Specifically, we demonstrate that exogenous styryl aryl azides can be converted into indoles inside living mammalian cells under photocatalytic conditions.

| S-EPMC10859955 | biostudies-literature

Green Synthesis of Luminescent Gold-Zinc Oxide Nanocomposites: Cell Imaging and Visible Light-Induced Dye Degradation.

Project description:Green synthesis of gold-zinc oxide (Au-ZnO) nanocomposite was successfully attempted under organic solvent-free conditions at room temperature. Prolonged stirring of the reaction mixture introduced crystallinity in the ZnO phase of Au-ZnO nanocomposites. Luminescence properties were observed in these crystalline Au-ZnO nanocomposites due to in situ embedding of gold nanoparticles (AuNP) of 5-6 nm diameter on the surface. This efficient strategy involved the reduction of Au(III) by Zn(0) powder in aqueous medium, where sodium citrate (NaCt) was the stabilizing agent. Reaction time and variation of reagent concentrations were investigated to control the Au:Zn ratio within the nanocomposites. The reaction with the least amount of NaCt for a long duration resulted in Au-ZnO/Zn(OH)2 nanocomposite. X-ray photoelectron spectroscopy (XPS) confirmed the formation of Zn(OH)2 and ZnO in the same nanocomposite. These nanocomposites were reconnoitered as bioimaging materials in human cells and applied for visible light-induced photodegradation of rhodamine-B dye.

| S-EPMC8080447 | biostudies-literature

Rhenium complexes with visible-light-induced anticancer activity.

Project description:Shedding light on the matter: Rhenium(I) indolato complexes with highly potent visible-light-triggered antiproliferative activity (complex 1: EC50 light=0.1 ?M vs EC50 dark=100 ?M) in 2D- and 3D-organized cancer cells are reported and can be traced back to an efficient generation of singlet oxygen, causing rapid morphological changes and an induction of apoptosis.

| S-EPMC3665699 | biostudies-literature

Visible-light photoredox synthesis of unnatural chiral α-amino acids.

Project description:Unnatural chiral α-amino acids are widely used in fields of organic chemistry, biochemistry and medicinal chemistry, and their synthesis has attracted extensive attention. Although the asymmetric synthesis provides some efficient protocols, noble and elaborate catalysts, ligands and additives are usually required which leads to high cost. Distinctly, it is attractive to make unnatural chiral α-amino acids from readily available natural α-amino acids through keeping of the existing chiral α-carbon. However, it is a great challenge to construct them under mild conditions. In this paper, 83 unnatural chiral α-amino acids were prepared at room temperature under visible-light assistance. The protocol uses two readily available genetically coded proteinogenic amino acids, L-aspartic acid and glutamic acid derivatives as the chiral sources and radical precursors, olefins, alkynyl and alkenyl sulfones, and 2-isocyanobiphenyl as the radical acceptors, and various unnatural chiral α-amino acids were prepared in good to excellent yields. The simple protocol, mild conditions, fast reactions, and high efficiency make the method an important strategy for synthesis of diverse unnatural chiral α-amino acids.

| S-EPMC4868990 | biostudies-literature

Fully Oxygen-Tolerant Visible-Light-Induced ATRP of Acrylates in Water: Toward Synthesis of Protein-Polymer Hybrids.

Project description:Over the last decade, photoinduced ATRP techniques have been developed to harness the energy of light to generate radicals. Most of these methods require the use of UV light to initiate polymerization. However, UV light has several disadvantages: it can degrade proteins, damage DNA, cause undesirable side reactions, and has low penetration depth in reaction media. Recently, we demonstrated green-light-induced ATRP with dual catalysis, where eosin Y (EYH2) was used as an organic photoredox catalyst in conjunction with a copper complex. This dual catalysis proved to be highly efficient, allowing rapid and well-controlled aqueous polymerization of oligo(ethylene oxide) methyl ether methacrylate without the need for deoxygenation. Herein, we expanded this system to synthesize polyacrylates under biologically relevant conditions using CuII/Me6TREN (Me6TREN = tris[2-(dimethylamino)ethyl]amine) and EYH2 at ppm levels. Water-soluble oligo(ethylene oxide) methyl ether acrylate (average M n = 480, OEOA480) was polymerized in open reaction vessels under green light irradiation (520 nm). Despite continuous oxygen diffusion, high monomer conversions were achieved within 40 min, yielding polymers with narrow molecular weight distributions (1.17 ≤ D̵ ≤ 1.23) for a wide targeted DP range (50-800). In situ chain extension and block copolymerization confirmed the preserved chain end functionality. In addition, polymerization was triggered/halted by turning on/off a green light, showing temporal control. The optimized conditions also enabled controlled polymerization of various hydrophilic acrylate monomers, such as 2-hydroxyethyl acrylate, 2-(methylsulfinyl)ethyl acrylate), and zwitterionic carboxy betaine acrylate. Notably, the method allowed the synthesis of well-defined acrylate-based protein-polymer hybrids using a straightforward reaction setup without rigorous deoxygenation.

| S-EPMC10019465 | biostudies-literature

Microstructure-Dependent Visible-Light Driven Photoactivity of Sputtering-Assisted Synthesis of Sulfide-Based Visible-Light Sensitizer onto ZnO Nanorods.

Project description:The ZnO-CdS core-shell composite nanorods with CdS shell layer thicknesses of 5 and 20 nm were synthesized by combining the hydrothermal growth of ZnO nanorods with the sputtering thin-film deposition of CdS crystallites. The microstructures and optical properties of the ZnO-CdS nanorods were associated with the CdS shell layer thickness. A thicker CdS shell layer resulted in a rougher surface morphology, more crystal defects, and a broader optical absorbance edge in the ZnO-CdS rods. The ZnO-CdS (20 nm) nanorods thus engaged in more photoactivity in this study. When they were further subjected to a postannealing procedure in ambient Ar/H₂, this resulted in the layer-like CdS shell layers being converted into the serrated CdS shell layers. By contrast, the ZnO-CdS nanorods conducted with the postannealing procedure exhibited superior photoactivity and photoelectrochemical performance; the substantial changes in the microstructures and optical properties of the composite nanorods following postannealing in this study might account for the observed results.

| S-EPMC5457004 | biostudies-other

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