Browse
Submit Data
Databases
API
Help

Dataset Information

15 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Copper-catalyzed O-alkenylation of phosphonates.

ABSTRACT: Copper catalysis allows the direct oxygen alkenylation of dialkyl phosphonates with alkenyl(aryl)iodonium salts with selective transfer of the alkenyl group. This novel methodology proceeds with a wide range of phosphonates under mild conditions and gives straightforward access to valuable enol phosphonates in very good yields.

SUBMITTER: Vazquez-Galinanes N

PROVIDER: S-EPMC7136550 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Copper-catalyzed <i>O</i>-alkenylation of phosphonates.

Vázquez-Galiñanes Nuria N Andón-Rodríguez Mariña M Gómez-Roibás Patricia P Fañanás-Mastral Martín M

Beilstein journal of organic chemistry 20200403

Copper catalysis allows the direct oxygen alkenylation of dialkyl phosphonates with alkenyl(aryl)iodonium salts with selective transfer of the alkenyl group. This novel methodology proceeds with a wide range of phosphonates under mild conditions and gives straightforward access to valuable enol phosphonates in very good yields. ...[more]

PMID: 32280389

Similar Datasets

Palladium-catalyzed ?-arylation of benzylic phosphonates.

Project description:A new synthetic route to access diarylmethyl phosphonates is presented. The transformation enables the introduction of aromatic groups on benzylic phosphonates via a deprotonative cross-coupling process (DCCP). The Pd(OAc)2/CataCXium A-based catalyst afforded a reaction between benzyl diisopropyl phosphonate derivatives and aryl bromides in good to excellent isolated yields (64-92%).

| S-EPMC3993846 | biostudies-other

Photoredox-Catalyzed Alkenylation of Benzylsulfonium Salts.

Project description:Visible light-mediated radical alkenylation of benzylsulfonium salts was achieved by means of fac-Ir(ppy)3 as a photocatalyst, giving allylbenzenes as products. A variety of functional groups, such as halogen, ester, and cyano, were well tolerated in this transformation. Starting benzylsulfonium salts could be readily prepared from benzyl alcohols by an acid-mediated substitution, increasing the synthetic utility of this transformation.

| S-EPMC6442929 | 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

Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds.

Project description:Herein we report a facile, mild reaction protocol to form carbon-carbon bonds in the absence of transition metal catalysts. We demonstrate the metal-free alkenylation reactions of aryl esters with ?-diazoesters to give highly functionalized enyne products. Catalytic amounts of tris(pentafluorophenyl)borane (10-20?mol?%) are employed to afford the C=C coupled products (31 examples) in good to excellent yields (36-87?%). DFT studies were used to elucidate the mechanism for this alkenylation reaction.

| S-EPMC7497215 | biostudies-literature

Palladium-Catalyzed Selective ?-Alkenylation of Pyridylmethyl Ethers with Vinyl Bromides.

Project description:An efficient palladium-catalyzed ?-alkenylation of pyridylmethyl ethers with vinyl bromides is presented. A Pd/NIXANTPHOS-based catalyst system enables a mild and chemoselective coupling between a variety of pyridylmethyl ethers and vinyl bromides in good to excellent yields. Under the mild conditions, ?,?-unsaturated products are obtained without isomerization or Heck byproducts observed.

| S-EPMC4887130 | biostudies-literature

Enantioselective alkenylation via nickel-catalyzed cross-coupling with organozirconium reagents.

Project description:A new family of organometallic compounds, organozirconium reagents, are shown to serve as suitable partners in cross-coupling reactions of (activated) secondary alkyl electrophiles. Thus, the first catalytic method for coupling secondary alpha-bromoketones with alkenylmetal reagents has been developed, specifically, a mild, versatile, and stereoconvergent carbon-carbon bond-forming process that generates potentially labile beta,gamma-unsaturated ketones with good enantioselectivity.

| S-EPMC2860276 | biostudies-literature

Palladium-Catalyzed Enantioselective Alkenylation of Enelactams Using a Relay Heck Strategy.

Project description:In this report, a palladium-catalyzed redox-relay Heck process to access optically active alkenylated ?,?-unsaturated lactams is described. Under mild reaction conditions, electron-deficient alkenyl triflates and electron-rich alkenyl iodonium salts undergo enantioselective and site-selective coupling with enelactams to deliver the products in high yields and excellent enantioselectivities. Furthermore, the products allow facile access to natural products such as (+)-calvine and (+)-2-epicalvine in addition to the bioactive molecule aza-goniothalamin.

| S-EPMC6731067 | biostudies-literature

Cobalt-catalyzed, aminoquinoline-directed C(sp²)-H bond alkenylation by alkynes.

Project description:A method for cobalt-catalyzed, aminoquinoline- and picolinamide-directed C(sp(2))-H bond alkenylation by alkynes was developed. The method shows excellent functional-group tolerance and both internal and terminal alkynes are competent substrates for the coupling. The reaction employs a Co(OAc)2?4?H2O catalyst, Mn(OAc)2 co-catalyst, and oxygen (from air) as a terminal oxidant.

| S-EPMC4167400 | biostudies-literature

Dehydrogenative alkenylation of uracils via palladium-catalyzed regioselective C-H activation.

Project description:A regioselective Pd-catalyzed cross-dehydrogenative coupling between uracils and alkenes is reported. This protocol provides easy access to a variety of 5-alkenyluracil structural motifs.

| S-EPMC3640306 | biostudies-literature

Silanol: a traceless directing group for Pd-catalyzed o-alkenylation of phenols.

Project description:A silanol-directed, Pd(II)-catalyzed C-H alkenylation of phenols is reported. This work features silanol, as a novel traceless directing group, and a directed o-C-H alkenylation of phenols. This new method allows for efficient synthesis of diverse alkenylated phenols, including an estrone derivative.

| S-EPMC3156791 | 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