Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Metal- and photocatalyst-free synthesis of 3-selenylindoles and asymmetric diarylselenides promoted by visible light.

ABSTRACT: A novel and sustainable procedure was developed for the synthesis of 3-selenylindoles employing diorganyl diselenides and indoles or electron-rich arenes as starting materials. Visible blue light was used to promote the reaction without employing transition metal complexes or organic photocatalysts as sensitizers. Additives such as strong oxidants or bases were not required. Moreover, ethanol was employed as a benign solvent under mild reaction conditions. Through this easy and eco-friendly approach, several 3-selenylindoles and a number of asymmetric diarylselenides were obtained in good to excellent isolated yields.

SUBMITTER: Lemir ID

PROVIDER: S-EPMC9067025 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Metal- and photocatalyst-free synthesis of 3-selenylindoles and asymmetric diarylselenides promoted by visible light.

Lemir Ignacio D ID Castro-Godoy Willber D WD Heredia Adrián A AA Schmidt Luciana C LC Argüello Juan E JE

RSC advances 20190723 39

A novel and sustainable procedure was developed for the synthesis of 3-selenylindoles employing diorganyl diselenides and indoles or electron-rich arenes as starting materials. Visible blue light was used to promote the reaction without employing transition metal complexes or organic photocatalysts as sensitizers. Additives such as strong oxidants or bases were not required. Moreover, ethanol was employed as a benign solvent under mild reaction conditions. Through this easy and eco-friendly appr ...[more]

PMID: 35519497

Similar Datasets

Visible light-promoted metal-free sp(3)-C-H fluorination.

Project description:Photoexcited acetophenone can catalyze the fluorination of unactivated C(sp(3))-H groups. While acetophenone, a colorless oil, only has a trace amount of absorption in the visible light region, its photoexcitation can be achieved by irradiation with light generated by a household compact fluorescent lamp (CFL). This operational simple method provides improved substrate scope for the direct incorporation of a fluorine atom into simple organic molecules. CFL-irradiation can also be used to promote certain classic UV-promoted photoreactions of colorless monoarylketones and enones/enals.

| S-EPMC4160356 | biostudies-literature

Visible-Light-Promoted Transition-Metal-Free Construction of 3-Perfluoroalkylated Thioflavones.

Project description:A visible-light-promoted transition-metal-free perfluoroalkylation/cyclization reaction was developed with 9-mesityl-10-methylacridinium perchlorate (Acr+-Mes·ClO4 -) as the photocatalyst, by which various perfluoroalkyl-substituted heterocycles including thioflavones, oxindoles, and quinoline-2,4(1H,3H)-diones were prepared at room temperature. Moreover, the potential of this sustainable method is demonstrated by the excellent in vitro anti-lymphoma and cervical carcinoma activity of the novel 3-perfluoroalkylated thioflavone 3m.

| S-EPMC9326344 | biostudies-literature

Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3 )-H Bonds*.

Project description:The metal-free activation of C(sp3 )-H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug molecules (celecoxib) and complex structures such as l-menthol, amino acids, and cholesterol derivatives. Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcohols and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.

| S-EPMC7898869 | biostudies-literature

Quantum dot-sensitized O-linked heptazine polymer photocatalyst for the metal-free visible light hydrogen generation.

Project description:Metal-free organic polymer photocatalysts have attracted dramatic attention in the field of visible light-induced hydrogen evolution reaction (HER). Herein, we showed a polymeric O-linked heptazine polymer (OLHP) decorated with S, N co-doped graphene quantum dots (S,N-GQDs) as a photosensitizer to generate hydrogen upon quantum dot sensitization. Both of these heptazine-based systems show effective photosensitization with strong π-π interactions and enhanced photocatalytic H2 generation (24 times) as metal-free systems. Electrochemical impedance and optical measurements show effective charge transfer kinetics with decreased charge recombination, which is responsible for the enhanced photocatalytic activity. As a result, a significant high apparent quantum yield (AQY) with highest value of 10.2% was obtained for our photocatalyst OLHP/S,N-GQD10.

| S-EPMC9056167 | biostudies-literature

Visible light-promoted metal-free C-H activation: diarylketone-catalyzed selective benzylic mono- and difluorination.

Project description:We report herein an operationally simple method for the direct conversion of benzylic C-H groups to C-F. We show that visible light can activate diarylketones to abstract a benzylic hydrogen atom selectively. Adding a fluorine radical donor yields the benzylic fluoride and regenerates the catalyst. The selective formation of mono- and difluorination products can be achieved by catalyst control. 9-Fluorenone catalyzes benzylic C-H monofluorination, while xanthone catalyzes benzylic C-H difluorination. The scope and efficiency of this new C-H fluorination method are significantly better than those of the existing methods. This is also the first report of selective C-H gem-difluorination.

| S-EPMC3874084 | biostudies-literature

Visible light-promoted transition metal-free direct C3-carbamoylation of 2H-Indazoles.

Project description:We reported a general transition metal-free transformation to access C3-carbamoylated 2H-indazoles via visible light-induced oxidative decarboxylation coupling, in the presence of oxamic acids as the coupling sources, 4CzIPN as the photocatalyst, and Cs2CO3 as the base. The great application potential of this mild condition is highlighted by the late-stage modification of drugs, N-terminal modification of peptides, and the good antitumor activity of the novel desired product.

| S-EPMC9745185 | biostudies-literature

Visible Light-Mediated Organoboron-Catalyzed Metal-Free Synthesis of Silanols from Silanes.

Project description:Herein, a four-coordinated organoboron compound, aminoquinoline diarylboron (AQDAB), is utilized as the photocatalyst in the oxidation of silane to silanol. This strategy effectively oxidizes Si-H bonds, affording Si-O bonds. Generally, the corresponding silanols can be obtained in moderate to good yields at room temperature under oxygen atmospheres, representing a green protocol to complement the existing preparation methods for silanols.

| S-EPMC10222655 | biostudies-literature

Visible-Light-Induced, Graphene Oxide-Promoted C3-Chalcogenylation of Indoles Strategy under Transition-Metal-Free Conditions.

Project description:An efficient and general method for the synthesis of 3-sulfenylindoles and 3-selenylindoles employing visible-light irradiation with graphene oxide as a promoter at room temperature has been achieved. The reaction features are high yields, simple operation, metal-free and iodine-free conditions, an easy-to-handle oxidant, and gram-scalable synthesis. This simple protocol allows one to access a wide range of 3-arylthioindoles, 3-arylselenylindoles, and even 3-thiocyanatoindoles with good to excellent yields.

| S-EPMC8839487 | biostudies-literature

Transition-metal-free α-arylation of oxindoles via visible-light-promoted electron transfer.

Project description:An operationally simple photochemical strategy for the direct arylation of oxindoles with (hetero)aryl halides in the absence of both transition metals and photoredox catalysts has been developed. The reaction provides an efficient way to construct various 3-aryloxindole building blocks of pharmaceutical interest at ambient temperature by using household compact fluorescent light (CFL) bulbs as the light source. Preliminarily, mechanistic studies revealed that the intermolecular electron transfer relied on the formation of photon-absorbing electron-donor-acceptor (EDA) complexes between electron-rich oxindole enolates and electron-deficient (hetero)aryl halides, and a radical chain mechanism was operative.

| S-EPMC6427940 | biostudies-literature

Solvent-free, visible-light photocatalytic alcohol oxidations applying an organic photocatalyst.

Project description:A method for the solvent-free photocatalytic conversion of solid and liquid substrates was developed, using a novel rod mill apparatus. In this setup, thin liquid films are realized which is crucial for an effective photocatalytic conversion due to the low penetration depth of light in heterogeneous systems. Several benzylic alcohols were oxidized with riboflavin tetraacetate as photocatalyst under blue light irradiation of the reaction mixture. The corresponding carbonyl compounds were obtained in moderate to good yields.

| S-EPMC5238574 | 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