Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of fluoranthenes by hydroarylation of alkynes catalyzed by gold(I) or gallium trichloride.

ABSTRACT: Electrophilic gold(I) catalyst 6 competes with GaCl(3) as the catalyst of choice in the synthesis of fluoranthenes by intramolecular hydroarylation of alkynes. The potential of this catalyst for the preparation of polyarenes is illustrated by a synthesis of two functionalized decacyclenes in a one-pot transformation in which three C-C bonds are formed with high efficiency.

SUBMITTER: Pascual S

PROVIDER: S-EPMC3252853 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of fluoranthenes by hydroarylation of alkynes catalyzed by gold(I) or gallium trichloride.

Pascual Sergio S Bour Christophe C de Mendoza Paula P Echavarren Antonio M AM

Beilstein journal of organic chemistry 20111114

Electrophilic gold(I) catalyst 6 competes with GaCl(3) as the catalyst of choice in the synthesis of fluoranthenes by intramolecular hydroarylation of alkynes. The potential of this catalyst for the preparation of polyarenes is illustrated by a synthesis of two functionalized decacyclenes in a one-pot transformation in which three C-C bonds are formed with high efficiency. ...[more]

PMID: 22238527

Similar Datasets

Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes.

Project description:In a simple procedure, the intramolecular hydroarylation of N-propargyl-pyrrole-2-carboxamides was accomplished with the aid of gold(III) catalysis. The reaction led to differently substituted pyrrolo[2,3-c]pyridine and pyrrolo[3,2-c]pyridine derivatives arising either from direct cyclization or from a formal rearrangement of the carboxamide group. Terminal alkynes are essential to achieve bicyclic pyrrolo-fused pyridinones by a 6-exo-dig process, while the presence of a phenyl group at the C-C triple bond promotes the 7-endo-dig cyclization giving pyrrolo-azepines.

| S-EPMC3252845 | biostudies-literature

Synthesis of flinderoles B and C by a gold-catalyzed allene hydroarylation().

Project description:The recent development of new gold(I) catalysis methodologies has opened the door to new disconnections for the total synthesis of bioactive complex molecules. Below is described the application of a gold(I)-catalyzed hydroarylation of an allene with indole toward the total synthesis of flinderoles B-C, members of a new class of antimalarial bisindole alkaloids isolated from plants of the Flindersia genus. The key gold(I) step establishes both the pyrrolidine and isobutenyl functionalities unique to these compounds. Other important steps of the synthesis include a convergent Horner-Wadsworth-Emmons olefination to construct the bridging alkene and a new strategy for ?-indole enolate alkylations.

| S-EPMC3389741 | biostudies-literature

Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones.

Project description:A series of propargylamides containing an electron-rich benzene ring was prepared through the Ugi reaction of 3,5-dimethoxyaniline with various propiolic acids, aldehydes and isocyanides. Subjecting these adducts to a gold-catalyzed intramolecular alkyne hydroarylation process allowed to efficiently construct the 2-quinolone core bearing a branched substituent on the nitrogen atom.

| S-EPMC6204774 | biostudies-literature

Gold(I)-catalyzed intramolecular hydroarylation of allenes.

Project description:Gold(I) complexes react with 4-allenyl arenes in an exo fashion to furnish vinyl-substituted benzocycles. Phosphite gold(I) monocations were found to be optimal, and the catalyst was tolerant of ethers, esters, and pyrroles. Reactions proceeded in unpurified solvent at room temperature.

| S-EPMC2924810 | biostudies-literature

Gold-Catalyzed Oxidative Coupling of Alkynes toward the Synthesis of Cyclic Conjugated Diynes.

Project description:A gold-catalyzed oxidative coupling of alkynes was developed as an efficient approach for the synthesis of challenging cyclic conjugated diynes (CCD). Compared to the classical copper-promoted oxidative coupling reaction of alkynes, this gold-catalyzed process exhibits a faster reaction rate due to the rapid reductive elimination from the Au(III) intermediate. This unique reactivity thus allowed a challenging diyne macrocyclization to take place in high efficiency. Condition screening revealed a [(n-Bu)4N]+[Cl-Au-Cl]- salt as the optimal pre-catalyst. Macrocycles with ring size between 13 to 28 atoms were prepared in moderate to good yields, which highlighted the broad substrate scope of this new strategy. Furthermore, the synthetic utilities of the cyclic conjugated diynes for copper-free click chemistry have been demonstrated, which showcased the potential application of this strategy in biological systems.

| S-EPMC6429935 | biostudies-literature

Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

Project description:A highly enantioselective carboalkoxylation of alkynes catalyzed by cationic (DTBM-MeO-Biphep)gold(I) complexes is reported. Various optically active ?-alkoxyindanone derivatives were obtained in good yields with high enantioselectivities. Furthermore, this methodology was extended to the enantioselective synthesis of 3-methoxycyclopentenones. The reaction is proposed to proceed through an enantioselective cyclization of intermediates containing vinylgold(I) and prochiral oxocarbenium moieties.

| S-EPMC3795527 | biostudies-literature

Gold-Catalyzed Regioselective Dimerization of Aliphatic Terminal Alkynes.

Project description:A gold-catalyzed regioselective homodimerization of aliphatic terminal alkynes is described. Bulky and less Lewis acidic tBuXPhosAuNTf(2) is the preferred catalyst, and the additive, anhydrous NaOAc, substantially facilitates the reaction.

| S-EPMC3419542 | biostudies-literature

Stereoselective Gold(I)-Catalyzed Intermolecular Hydroalkoxlation of Alkynes.

Project description:We report the use of cationic gold complexes [Au(NHC)(CH3CN)][BF4] and [{Au(NHC)}2(?-OH)][BF4] (NHC = N-heterocyclic carbene) as highly active catalysts in the solvent-free hydroalkoxylation of internal alkynes using primary and secondary alcohols. Using this simple protocol, a broad range of (Z)-vinyl ethers were obtained in excellent yields and high stereoselectivities. The methodology allows for the use of catalyst loadings as low as 200 ppm for the addition of primary alcohols to internal alkynes (TON = 35 000, TOF = 2188 h-1).

| S-EPMC5745073 | biostudies-literature

Mechanistic surprises in the gold(I)-catalyzed intramolecular hydroarylation of allenes.

Project description: Not available

| S-EPMC2978329 | biostudies-literature

Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation.

Project description:Metal-catalyzed reactions have revolutionized synthetic chemistry, allowing access to unprecedented molecular architectures with powerful properties and activities. Nonetheless, some transformations remain sparse in number, or out of reach, even with the diverse modern catalytic chemical arsenal, including bimolecular alkene hydroarylation reactions. We report here a broad-scope, palladium-catalyzed pyrroline hydroarylation process that gives 3-aryl pyrrolidines, a class of small molecules with potency in a diverse range of biological scenarios. Thus, whereas N-acyl pyrrolines usually undergo palladium-catalyzed arylation to give alkene products, the corresponding reactions of N-alkyl pyrrolines deliver products of hydroarylation, pyrrolidines. The process has broad substrate scope and can be used to directly deliver drug-like molecules in a single step from readily available precursors.

| S-EPMC6240703 | 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