Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Palladium-catalyzed 2,5-diheteroarylation of 2,5-dibromothiophene derivatives.

ABSTRACT: Conditions allowing the one pot 2,5-diheteroarylation of 2,5-dibromothiophene derivatives in the presence of palladium catalysts are reported. Using KOAc as the base, DMA as the solvent and only 0.5-2 mol % palladium catalysts, the target 2,5-diheteroarylated thiophenes were obtained in moderate to good yields and with a wide variety of heteroarenes such as thiazoles, thiophenes, furans, pyrroles, pyrazoles or isoxazoles. Moreover, sequential heteroarylation reactions allow the access to 2,5-diheteroarylated thiophenes bearing two different heteroaryl units.

SUBMITTER: Belkessam F

PROVIDER: S-EPMC4273267 | biostudies-other | 2014

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

Palladium-catalyzed 2,5-diheteroarylation of 2,5-dibromothiophene derivatives.

Belkessam Fatma F Mohand Aidene A Soulé Jean-François JF Elias Abdelhamid A Doucet Henri H

Beilstein journal of organic chemistry 20141209

Conditions allowing the one pot 2,5-diheteroarylation of 2,5-dibromothiophene derivatives in the presence of palladium catalysts are reported. Using KOAc as the base, DMA as the solvent and only 0.5-2 mol % palladium catalysts, the target 2,5-diheteroarylated thiophenes were obtained in moderate to good yields and with a wide variety of heteroarenes such as thiazoles, thiophenes, furans, pyrroles, pyrazoles or isoxazoles. Moreover, sequential heteroarylation reactions allow the access to 2,5-dih ...[more]

PMID: 25550758

Similar Datasets

Palladium-catalyzed asymmetric dearomatization of naphthalene derivatives.

Project description:An intramolecular enantioselective metal-catalyzed dearomatization reaction is described. This procedure allows the dearomatization of naphthalene derivatives through an electrophilic aromatic substitution-type reaction on a Pd(II) intermediate. The high yields and enantioselectivities achieved make this procedure a valuable method for synthetic chemists.

| S-EPMC2748791 | biostudies-literature

Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives.

Project description:A regioselective and enantioselective palladium-catalyzed relay Heck alkenylation of alkenylbenzene derivatives to construct remote stereocenters is disclosed. Various β-substituted styrenes were readily obtained in moderate yields with good to excellent levels of enantioselectivity. This strategy provides rapid access to enantioenriched δ, ε, ζ, and η-alkenyl aryl compounds from simple starting materials. Mechanistic studies suggest that termination of the relay reaction is controlled by affinity of the arene for the Pd complex during migration.

| S-EPMC6685350 | biostudies-literature

Photocatalytic Palladium-Catalyzed Fluoroalkylation of Styrene Derivatives.

Project description:A visible light induced palladium-catalyzed fluoroalkylation method was developed. The Heck-type alkyl coupling reaction enables the introduction of trifluoroethyl, difluoroethyl and other fluoroalkyl fragment into styrenes under mild reaction conditions without the use of additional photosensitizers and ensures access to fluoroalkylated olefins on a broad scale.

| S-EPMC7587045 | biostudies-literature

Palladium(III)-catalyzed fluorination of arylboronic acid derivatives.

Project description:A practical, palladium-catalyzed synthesis of aryl fluorides from arylboronic acid derivatives is presented. The reaction is operationally simple and amenable to multigram-scale synthesis. Evaluation of the reaction mechanism suggests a single-electron-transfer pathway, involving a Pd(III) intermediate that has been isolated and characterized.

| S-EPMC3820116 | biostudies-literature

Palladium-catalyzed hydrofunctionalization of vinyl phenol derivatives with heteroaromatics.

Project description:A hydroheteroarylation reaction of vinyl phenols using an alkyl chloride as the sacrificial hydride source is reported. The method tolerates a wide range of heterocycles as the exogenous nucleophile including indoles and pyrroles. The resulting products are easily processed to biologically relevant scaffolds.

| S-EPMC3324091 | biostudies-literature

Palladium(II)-catalyzed enantio- and diastereoselective synthesis of pyrrolidine derivatives.

Project description:A palladium-catalyzed enantio- and diastereoselective synthesis of pyrrolidine derivatives is described. Initial intramolecular nucleopalladation of the tethered protected amine forms the pyrrolidine moiety and a quinone methide intermediate. A second nucleophile adds intermolecularly to afford diverse products in high enantio- and diastereoselectivity.

| S-EPMC3459323 | biostudies-literature

The palladium-catalyzed anti-Markovnikov hydroalkylation of allylic alcohol derivatives.

Project description:A palladium-catalyzed hydroalkylation reaction of protected allylic alcohols using alkylzinc bromide reagents is reported. This account includes numerous allylic, homoallylic, and bishomoallylic alcohol derivatives, all with a uniform selectivity of >20:1 for the anti-Markovnikov product. The reaction features the ability to deliver enantiomerically enriched alcohols in unfunctionalized regions, which results from the catalyst avoiding β-hydride elimination at the allylic position.

| S-EPMC3539300 | biostudies-literature

Palladium-Catalyzed Asymmetric Allylic Alkylations with Toluene Derivatives as Pronucleophiles.

Project description:The first two highly enantioselective palladium-catalyzed allylic alkylations with benzylic nucleophiles, activated with Cr(CO)3 , have been developed. These methods enable the enantioselective synthesis of α-2-propenyl benzyl motifs, which are important scaffolds in natural products and pharmaceuticals. A variety of cyclic and acyclic allylic carbonates are competent electrophilic partners furnishing the products in excellent enantioselectivity (up to 99 % ee and 92 % yield). This approach was employed to prepare a nonsteroidal anti-inflammatory drug analogue.

| S-EPMC4836847 | biostudies-literature

Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation.

Project description:The aminocarbonylation of 6-iodoquinoline has been investigated in the presence of large series of amine nucleophiles, providing an efficient synthetic route for producing various quinoline-6-carboxamide and quinoline-6-glyoxylamide derivatives. It was shown, after detailed optimization study, that the formation of amides and ketoamides is strongly influenced by the reaction conditions. Performing the reactions at 40 bar of carbon monoxide pressure in the presence of Pd(OAc)2/2 PPh3, the corresponding 2-ketocarboxamides were formed as major products (up to 63%). When the monodentate triphenylphosphine was replaced by the bidentate XantPhos, the quinoline-6-carboxamide derivatives were synthesized almost exclusively under atmospheric conditions (up to 98%). The isolation and characterization of the new carbonylated products of various structures were also accomplished. Furthermore, the structure of three new mono- and double-carbonylated compounds were unambiguously established by using a single-crystal XRD study.

| S-EPMC8746719 | biostudies-literature

Palladium-catalyzed aerobic oxidative dehydrogenation of cyclohexenes to substituted arene derivatives.

Project description:A palladium(II) catalyst system has been identified for aerobic dehydrogenation of substituted cyclohexenes to the corresponding arene derivatives. Use of sodium anthraquinone-2-sulfonate (AMS) as a cocatalyst enhances the product yields. A wide range of functional groups are tolerated in the reactions, and the scope and limitations of the method are described. The catalytic dehydrogenation of cyclohexenes is showcased in an efficient route to a phthalimide-based TRPA1 activity modulator.

| S-EPMC4524661 | 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