Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

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

ABSTRACT: 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].

SUBMITTER: He P

PROVIDER: S-EPMC2597418 | biostudies-literature | 2007 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

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

He Ping P Lu Yong Y Dong Cheng-Guo CG Hu Qiao-Sheng QS

Organic letters 20070101 2

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 ca ...[more]

PMID: 17217300

Similar Datasets

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

Project description:Phosphinite- and phosphite-based Type I palladacycle-catalyzed additions of arylboronic acids with aldehydes, α,β-unsaturated ketones, α-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

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

Catalytic asymmetric addition of diphenylzinc to cyclic alpha,beta-unsaturated ketones.

Project description:We have examined the use of our bis(sulfonamide) diol ligand (1) in the asymmetric addition of phenyl groups to cyclic alpha,beta-unsaturated ketones. Good to excellent enantioselectivities have been obtained with cyclic enones bearing alkyl substituents in the 2 position (71-97% enantiomeric excess). Furthermore, excellent enantioselectivities have been observed in the asymmetric phenylation of cyclic enones with 2-iodo and 2-bromo substituents. The results of this study broaden the scope of the asymmetric additions to ketones promoted by the titanium catalyst derived from ligand 1.

| S-EPMC397398 | biostudies-literature

Asymmetric aza-Michael reactions of alpha,beta-unsaturated ketones with bifunctional organic catalysts.

Project description: Not available

| S-EPMC2652737 | biostudies-literature

Asymmetric vinylogous aldol addition of alkylidene oxindoles on trifluoromethyl-α,β-unsaturated ketones.

Project description:A novel vinylogous aldol addition of alkylidene oxindole with 1-trifluoromethyl-3-alkylidene-propan-2-ones is presented. The reaction, catalyzed by a bifunctional tertiary amine, provides an efficient application of the vinylogous reactivity of oxindoles for the preparation of enantioenriched trifluoromethylated allylic alcohols.

| S-EPMC9086480 | biostudies-literature

Nickel-catalyzed cycloadditions of unsaturated hydrocarbons, aldehydes, and ketones.

Project description:The nickel-catalyzed cycloaddition of unsaturated hydrocarbons and carbonyls is reported. Diynes and enynes were used as coupling partners. Carbonyl substrates include both aldehdyes and ketones. Reactions of diynes and aldehydes afforded the [3,3] electrocyclic ring-opened tautomers, rather than pyrans, in high yields. The cycloaddition reaction of enynes and aldehydes afforded two distinct products. A new carbon-carbon bond is formed, prior to a competitive beta-hydrogen elimination of a nickel alkoxide, between the carbonyl carbon and either one of the carbons of the olefin or the alkyne. The steric hindrance of the enyne greatly affected the chemoselectivity of the cycloaddition of enynes and aldehydes. In some cases, dihydropyran was also formed. The scope of the cycloaddition reaction was expanded to include the coupling of enynes and ketones. No beta-hydrogen elimination was observed in cycloaddition reaction of enynes and ketones. Instead, C-O bond-forming reductive elimination occurred exclusively to afford dihydropyrans in excellent yields. In all cases, complete chemoselectivity was observed; only dihydropyrans where the carbonyl carbon forms a carbon-carbon bond with a carbon of the olefin, rather than of the alkyne, were observed. All cycloaddition reactions occur at room temperature and employ nickel catalysts bearing the hindered 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr) or its saturated analogue, 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazolin-2-ylidene (SIPr).

| S-EPMC4144363 | biostudies-literature

DBU-Mediated Addition of α-Nitroketones to α-Cyano-enones and α,β-Unsaturated α-Ketoesters: Synthesis of Dihydrofurans and Conjugated Dienes.

Project description:1,8-Diazabicyclo[5.4.0]undec-7-ene-mediated reactions of α-nitroketones with α-cyano-enones and α,β-unsaturated α-ketoesters have been developed. The products, namely, dihydrofurans and conjugated dienes, were isolated in moderate to good yields, and a range of substitutions were tolerated.

| S-EPMC6648157 | biostudies-literature

Enantioselective Michael addition of malonates to α,β-unsaturated ketones catalyzed by 1,2-diphenylethanediamine.

Project description:A general and highly enantioselective Michael addition of malonates to cinnamones and chalcones has been developed. The commercially available 1,2-diphenylethanediamine could be directly utilized as the organocatalyst to furnish the desired adducts in satisfactory yield (61-99%) and moderate to excellent enantiopurity (65 to >99% ee). β-Ketoester was also a competent donor and was employed to construct densely functionalized cyclohexenones via a tandem Michael-aldol condensation process.

| S-EPMC9091971 | biostudies-literature

Copper-catalyzed cascade annulation of unsaturated α-bromocarbonyls with enynals: a facile access to ketones from aldehydes.

Project description:A Cu-catalyzed cascade annulation of enynals with alkenyl or alkynyl α-bromocarbonyls for the synthesis of various cyclohexenone-fused polycyclic compounds is described. Up to six new C-C bonds and four new carbocycles can be established in a single reaction, highlighting the high efficiency and step-economics of this protocol. This reaction offers a novel and straightforward entry to the synthesis of ketones featuring the addition of carbon radicals to aldehydes.

| S-EPMC6014112 | 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