Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Aryl ketone synthesis via tandem orthoplatinated triarylphosphite-catalyzed addition reactions of arylboronic acids with aldehydes followed by oxidation.

ABSTRACT: Tandem orthoplatinated triaryl phosphite-catalyzed addition reactions of arylboronic acids with aldehydes followed by oxidation to yield aryl ketones is described. 3-Pentanone was identified as a suitable oxidant for the tandem aryl ketone formation reaction. By using microwave energy, aryl ketones were obtained in high yields with the catalyst loading as low as 0.01%.

SUBMITTER: Liao YX

PROVIDER: S-EPMC2975394 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Aryl ketone synthesis via tandem orthoplatinated triarylphosphite-catalyzed addition reactions of arylboronic acids with aldehydes followed by oxidation.

Liao Yuan-Xi YX Hu Qiao-Sheng QS

The Journal of organic chemistry 20101001 20

Tandem orthoplatinated triaryl phosphite-catalyzed addition reactions of arylboronic acids with aldehydes followed by oxidation to yield aryl ketones is described. 3-Pentanone was identified as a suitable oxidant for the tandem aryl ketone formation reaction. By using microwave energy, aryl ketones were obtained in high yields with the catalyst loading as low as 0.01%. ...[more]

PMID: 20849092

Similar Datasets

Tandem Aldol Condensation - Platinacycle-Catalyzed Addition Reactions of Aldehydes, Methyl Ketones and Arylboronic Acids.

Project description:Tandem aldol condensation of aldehydes with methyl ketones followed by anionic four-electron donor-based (Type I) platinacycle-catalyzed addition reactions of arylboronic acids to form ?-arylated ketones is described. Good to excellent yields of ?-arylated ketones were obtained for the tandem reactions of aromatic/aliphatic aldehydes, methyl ketones and arylboronic acids, and moderate yields were observed for the tandem reaction with ?, ?-unsaturated aldehydes as the aldehyde source.

| S-EPMC3547403 | biostudies-other

Sequential aldol condensation-transition metal-catalyzed addition reactions of aldehydes, methyl ketones, and arylboronic acids.

Project description:Sequential aldol condensation of aldehydes with methyl ketones followed by transition metal-catalyzed addition reactions of arylboronic acids to form ?-substituted ketones is described. By using the 1,1'-spirobiindane-7,7'-diol (SPINOL)-based phosphite, an asymmetric version of this type of sequential reaction, with up to 92% ee, was also realized. Our study provided an efficient method to access ?-substituted ketones and might lead to the development of other sequential/tandem reactions with transition metal-catalyzed addition reactions as the key step.

| S-EPMC3077042 | biostudies-literature

Ir(COD)Cl]2/Tris(2,4-di-t-butylphenyl)phosphite-Catalyzed Addition Reactions of Arylboronic Acids with Aldehydes.

Project description:[Ir(COD)Cl]2/tris(2,4-di-t-butylphenyl)phosphite-catalyzed addition reactions of arylboronic acids with aldehydes were described. The Ir(I) catalyst, generated from [Ir(COD)Cl]2 and tris(2,4-di-t-butylphenyl)phosphite, was an efficient catalyst system for the addition reactions of a variety of arylboronic acids with aromatic and aliphatic aldehydes. The easy availability of the catalyst and good yields make these reactions potentially useful in organic synthesis.

| S-EPMC6186456 | biostudies-literature

Gold(i)-catalyzed addition of aldehydes to cyclopropylidene bearing 6-aryl-1,5-enynes.

Project description:A diastereoselective, gold-catalyzed cascading cycloisomerization of alkylidene cyclopropane bearing 1,5-enynes that terminates in a cyclo-addition of aldehydes has been developed. This diastereoselective reaction provides convergent access to novel polycyclic molecular structures (18 examples), and tolerates a diverse scope of aldehydes. Mechanistic studies reveal that the catalytic cycle rests at a digold off-cycle intermediate, one of which was isolated.

| S-EPMC5134929 | biostudies-literature

Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes To Form Hindered Secondary Alcohols.

Project description:Transition-metal-catalyzed addition of aryl halides across carbonyls remains poorly developed, especially for aliphatic aldehydes and hindered substrate combinations. We report here that simple nickel complexes of bipyridine and PyBox can catalyze the addition of aryl halides to both aromatic and aliphatic aldehydes using zinc metal as the reducing agent. This convenient approach tolerates acidic functional groups that are not compatible with Grignard reactions, yet sterically hindered substrates still couple in high yield (33 examples, 70% average yield). Mechanistic studies show that an arylnickel, and not an arylzinc, adds efficiently to cyclohexanecarboxaldehyde, but only in the presence of a Lewis acid co-catalyst (ZnBr2).

| S-EPMC6368192 | biostudies-literature

Triphenylphosphine as a ligand for room-temperature Ni(0)-catalyzed cross-coupling reactions of aryl chlorides with arylboronic acids.

Project description:Room-temperature Ni(0)-catalyzed cross-coupling reactions of deactivated aryl chlorides with arylboronic acids with inexpensive triphenylphosphine (PPh3) as a supporting ligand have been accomplished in good to excellent yields. Air-stable Ni(PPh3)2Cl2 has also been established as catalyst precursor, and highly active nickel catalysts were obtained when the reduction of Ni(PPh3)2Cl2 with n-BuLi was carried out in the presence of an aryl chloride.

| S-EPMC2531206 | biostudies-literature

Anionic four-electron donor-based palladacycles as catalysts for addition reactions of arylboronic acids with alpha,beta-unsaturated ketones, aldehydes, and alpha-ketoesters.

Project description:Anionic four-electron donor-based palladacycle-catalyzed 1,4-additions of arylboronic acids with alpha,beta-unsaturated ketones and 1,2-additions of arylboronic acids with aldehydes and alpha-ketoesters are described. Our study demonstrated that palladacycles were highly efficient, practical catalysts for these addition reactions. The work described here not only opened a new paradigm for the application of palladacycles, but may also pave the road for other metalacycles as practically useful catalysts for such addition reactions including asymmetric ones. [reaction: see text].

| S-EPMC2597418 | biostudies-literature

Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids.

Project description:A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.

| S-EPMC3766840 | biostudies-literature

Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to heterocyclic acceptors.

Project description:Flava Flavanone: Asymmetric conjugate additions to chromones and 4-quinolones are reported utilizing a single catalyst system formed in situ from Pd(OCOCF(3))(2) and (S)-tBuPyOX. Notably, these reactions are performed in wet solvent under ambient atmosphere, and employ readily available arylboronic acids as the nucleophile, thus providing ready access to these asymmetric heterocycles (see scheme).

| S-EPMC3753812 | biostudies-literature

Phosphinite- and phosphite-based Type I palladacycles as highly active catalysts for addition reactions of arylboronic acids with aldehydes, ?,?-unsaturated ketones, ?-ketoesters, and aldimines.

Project description:Phosphinite- and phosphite-based Type I palladacycle-catalyzed additions of arylboronic acids with aldehydes, ?,?-unsaturated ketones, ?-ketoesters and aldimines are described. Our study showed that readily available phosphinite- and phosphite-based Type I palladacycles could possess higher catalytic activity than phosphine-based palladacycles and were highly active, practical catalysts. Our study may pave the road for development of optically active phosphinite- and phosphite-based palladacycles for asymmetric catalysis.

| S-EPMC2031830 | 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