Browse
Submit Data
Databases
API
Help

Dataset Information

23 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Highly efficient route to fused polycyclic aromatics via palladium-catalyzed aryne annulation by aryl halides.

ABSTRACT: Polycyclic aromatic and heteroaromatic hydrocarbons have been synthesized in high yield by two different processes involving the Pd-catalyzed annulation of arynes. The first process involves a Pd-catalyzed annulation of arynes by 2-halobiaryls and related vinylic halides. The second process utilizes a Pd-catalyzed double annulation of arynes by simple aryl halides. Both processes appear to involve the catalytic, stepwise coupling of two very reactive substrates, an aryne and an organopalladium species, to generate excellent yields of cross-coupled products.

SUBMITTER: Liu Z

PROVIDER: S-EPMC2529458 | biostudies-literature | 2007 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Highly efficient route to fused polycyclic aromatics via palladium-catalyzed aryne annulation by aryl halides.

Liu Zhijian Z Larock Richard C RC

The Journal of organic chemistry 20070101 1

Polycyclic aromatic and heteroaromatic hydrocarbons have been synthesized in high yield by two different processes involving the Pd-catalyzed annulation of arynes. The first process involves a Pd-catalyzed annulation of arynes by 2-halobiaryls and related vinylic halides. The second process utilizes a Pd-catalyzed double annulation of arynes by simple aryl halides. Both processes appear to involve the catalytic, stepwise coupling of two very reactive substrates, an aryne and an organopalladium s ...[more]

PMID: 17194103

Similar Datasets

Palladium-catalyzed synthesis of 9-fluorenylidenes through aryne annulation.

Project description:The palladium-catalyzed annulation of arynes by substituted o-halostyrenes produces substituted 9-fluorenylidenes in good yields. This methodology provides this important carbocyclic ring system in a single step, which involves the generation of two new carbon-carbon bonds, occurs under relatively mild reaction conditions, and tolerates a variety of functional groups, including cyano, ester, aldehyde, and ketone groups.

| S-EPMC2731569 | biostudies-literature

Palladium-catalyzed nitromethylation of aryl halides: an orthogonal formylation equivalent.

Project description:An efficient cross-coupling reaction of aryl halides and nitromethane was developed with the use of parallel microscale experimentation. The arylnitromethane products are precursors for numerous useful synthetic products. An efficient method for their direct conversion to the corresponding oximes and aldehydes in a one-pot operation has been discovered. The process exploits inexpensive nitromethane as a carbonyl equivalent, providing a mild and convenient formylation method that is compatible with many functional groups.

| S-EPMC3430980 | biostudies-literature

Palladium-catalyzed intermolecular transthioetherification of aryl halides with thioethers and thioesters.

Project description:Functional group transfer reactions are an important synthetic tool in modern organic synthesis. Herein, we developed a new palladium-catalyzed intermolecular transthioetherification reaction of aryl halides with thioethers and thioesters. The synthetic utility and practicality of this catalytic protocol are demonstrated in a wide range of successful transformations (>70 examples). This catalytic protocol is applicable in carbonylative coupling processes as well, and the first example of carbonylative methylthioesterification of aryl halides has been achieved. Notably, this work also provides an approach to using natural products, such as methionine and selenomethionine, as the functional group sources.

| S-EPMC8150098 | biostudies-literature

Palladium-catalyzed regiocontrolled alpha-arylation of trimethylsilyl enol ethers with aryl halides.

Project description:Inter- and intramolecular arylations of trimethylsilyl enol ethers with aryl halides are accomplished regiospecifically in the presence of a palladium catalyst and tributyltin fluoride in refluxing benzene or toluene. The optimal catalyst system called for the use of Pd2(dba)3 and tri-tert-butylphosphine in ca. 1:2 ratio. Aryl iodides, bromides, and chlorides are all effective arylation partners in this reaction. [reaction: see text]

| S-EPMC2518395 | biostudies-literature

Palladium-catalyzed intramolecular carbopalladation/cyclization cascade: access to polycyclic N-fused heterocycles.

Project description:An efficient palladium-catalyzed intramolecular carbopalladation/cyclization cascade toward tetra- and pentacyclic N-fused heterocycles has been developed. This transformation proceeds via the palladium-catalyzed coupling of aryl halides with internal propargylic esters or ethers followed by the 5-endo-dig cyclization leading to polycyclic pyrroloheterocycles in moderate to excellent yields.

| S-EPMC3131228 | biostudies-literature

A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide.

Project description:We describe here a tandem catalytic route to prepare imidazoles in a single operation from aryl iodides, imines and CO. The reaction involves a catalytic carbonylation of aryl halides with imines to form 1,3-dipoles, which undergo spontaneous 1,3-dipolar cycloaddition. Overall, this offers an alternative to coupling reactions to construct the (hetero)aryl-imidazole motif, where variation of the building blocks can allow the synthesis of broad families of imidazoles with independent control of all substituents.

| S-EPMC5354067 | biostudies-literature

Palladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis.

Project description:A strategy for DNA-compatible, palladium-catalyzed hydroxycarbonylation of (hetero)aryl halides on DNA-chemical conjugates has been developed. This method generally provided the corresponding carboxylic acids in moderate to very good conversions for (hetero)aryl iodides and bromides, and in poor to moderate conversions for (hetero)aryl chlorides. These conditions were further validated by application within a DNA-encoded chemical library synthesis and subsequent discovery of enriched features from the library in selection experiments against two protein targets.

| S-EPMC6706801 | biostudies-literature

Minimizing the amount of nitromethane in palladium-catalyzed cross-coupling with aryl halides.

Project description:A method for the formation of arylnitromethanes is described that employs readily available aryl halides or triflates and small amounts of nitromethane in a dioxane solvent, thereby reducing the hazards associated with this reagent. Specifically, 2-10 equiv (1-5% v/v) of nitromethane can be employed in comparison to prior work that used nitromethane as solvent (185 equiv). The present transformation provides high yields at relatively low temperatures and tolerates an array of functionality, including heterocycles and substantial steric encumbrance.

| S-EPMC3778657 | biostudies-literature

A General and Practical Palladium-Catalyzed Direct ?-Arylation of Amides with Aryl Halides.

Project description:An efficient system for the direct catalytic intermolecular ?-arylation of acetamide derivatives with aryl bromides and chlorides is presented. The palladium catalyst is supported by Kwong's indole-based phosphine ligand and provides monoarylated amides in up to 95% yield. Excellent chemoselectivities (>10:1) in the mono- and diarylation with aryl bromides were achieved by careful selection of bases, solvents, and stoichiometry. Under the coupling conditions, the weakly acidic ?-protons of amides (pKa up to 35) were reversibly depotonated by LiO t Bu, NaO t Bu, or NaN(SiMe3)2.

| S-EPMC3994175 | biostudies-literature

Mild palladium-catalyzed cyanation of (hetero)aryl halides and triflates in aqueous media.

Project description:A mild, efficient, and low-temperature palladium-catalyzed cyanation of (hetero)aryl halides and triflates is reported. Previous palladium-catalyzed cyanations of (hetero)aryl halides have required higher temperatures to achieve good catalytic activity. This current reaction allows the cyanation of a general scope of (hetero)aryl halides and triflates at 2-5 mol % catalyst loadings with temperatures ranging from rt to 40 °C. This mild method was applied to the synthesis of lersivirine, a reverse transcriptase inhibitor.

| S-EPMC4301087 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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