Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

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

ABSTRACT: 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.

SUBMITTER: Liang K

PROVIDER: S-EPMC6427940 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Transition-metal-free α-arylation of oxindoles <i>vi</i>a visible-light-promoted electron transfer.

Liang Kangjiang K Li Na N Zhang Yang Y Li Tao T Xia Chengfeng C

Chemical science 20190122 10

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 transfe ...[more]

PMID: 30996886

Similar Datasets

Practical, scalable, and transition metal-free visible light-induced heteroarylation route to substituted oxindoles.

Project description:The synthetic application of (hetero)aryl radicals in organic synthesis has been known since the last century. However, their applicability has significantly suffered from ineffective generation protocols. Herein, we present a visible-light-induced transition metal-free (hetero)aryl radical generation from readily available (hetero)aryl halides for the synthesis of 3,3'-disubstituted oxindoles. This transformation is amenable to a wide range of (hetero)aryl halides as well as several easily accessible acrylamides, and it is also scalable to multigram synthesis. Finally, the versatility of the oxindole products is demonstrated through their conversion to a variety of useful intermediates applicable to target-directed synthesis.

| S-EPMC9890556 | 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 transition metal-free direct C3-carbamoylation of 2<i>H</i>-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-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

A visible-light-induced, metal-free bis-arylation of 2,5-dichlorobenzoquinone.

Project description:A metal-free protocol for the direct bis-arylation of 2,5-dichlorobenzoquinone with aryldiazonium salts is reported. The reactive salts are generated in situ and converted to radicals through irradiation with visible light. Reaction products precipitate from the solvent, eliminating the need for purification and thus providing a novel green method for the synthesis of versatile bis-electrophiles.

| S-EPMC8450952 | biostudies-literature

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 C-S Cross-Coupling via Intermolecular Charge Transfer.

Project description:Disclosed is a mild, scalable, visible-light-promoted cross-coupling reaction between thiols and aryl halides for the construction of C-S bonds in the absence of both transition metal and photoredox catalysts. The scope of aryl halides and thiol partners includes over 60 examples and therefore provides an entry point into various aryl thioether building blocks of pharmaceutical interest. Furthermore, to demonstrate its utility, this C-S coupling protocol was applied in drug synthesis and late-stage modifications of active pharmaceutical ingredients. UV-vis spectroscopy and time-dependent density functional theory calculations suggest that visible-light-promoted intermolecular charge transfer within the thiolate-aryl halide electron donor-acceptor complex permits the reactivity in the absence of catalyst.

| S-EPMC5920654 | biostudies-literature

Visible-Light-Induced Singlet Oxygen-Promoted Arylation and Alkylation of Quinoxalin-2(1H)-ones and Quinolines.

Project description:We report a green and efficient visible-light-driven method for the arylation and alkylation of quinoxalin-2(1H)-ones and quinolines. This catalyst-free process utilizes air as the oxidant, offering mild reaction conditions, environmental sustainability, and broad functional group compatibility. The approach enables the synthesis of aryl and alkyl derivatives of quinoxalin-2(1H)-ones and quinolines with high to excellent yields.

| S-EPMC11547374 | biostudies-literature

Visible-light-switched electron transfer over single porphyrin-metal atom center for highly selective electroreduction of carbon dioxide.

Project description:External fields are introduced to catalytic processes to improve catalytic activities. The light field effect plays an important role in electrocatalytic processes, but is not fully understood. Here we report a series of photo-coupled electrocatalysts for CO2 reduction by mimicking the structure of chlorophyll. The porphyrin-Au catalyst exhibits a high turnover frequency of 37,069 h-1 at -1.1 V and CO Faradaic efficiency (FE) of 94.2% at -0.9 V. Under visible light, the electrocatalyst reaches similar turnover frequency and FE with potential reduced by ~ 130 mV. Interestingly, the light-induced positive shifts of 20, 100, and 130 mV for porphyrin-Co, porphyrin-Cu, and porphyrin-Au electrocatalysts are consistent with their energy gaps of 0, 1.5, and 1.7 eV, respectively, suggesting the porphyrin not only serves as a ligand but also as a photoswitch to regulate electron transfer pathway to the metal center.

| S-EPMC6710284 | biostudies-literature

Visible-light Promoted Atom Transfer Radical Addition-Elimination (ATRE) Reaction for the Synthesis of Fluoroalkylated Alkenes Using DMA as Electron-Donor.

Project description:Here, we describe a mild, catalyst-free and operationally-simple strategy for the direct fluoroalkylation of olefins driven by the photochemical activity of an electron donor-acceptor (EDA) complex between DMA and fluoroalkyl iodides. The significant advantages of this photochemical transformation are high efficiency, excellent functional group tolerance, and synthetic simplicity, thus providing a facile route for further application in pharmaceuticals and life sciences.

| S-EPMC7036948 | 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