Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Markovnikov-addition of H-phosphonates to terminal alkynes under metal- and solvent-free conditions.

ABSTRACT: An addition of H-phosphonates to aryl alkynes was realized under solvent- and metal-free conditions, affording Markovnikov-selective α-vinylphosphonates in moderate to good yields. A wide range of aryl alkynes could be applied for the reaction. A tentative mechanism of addition-substitution was proposed based on in situ ³¹P {¹H} NMR studies.

SUBMITTER: Xin N

PROVIDER: S-EPMC9036860 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Markovnikov-addition of H-phosphonates to terminal alkynes under metal- and solvent-free conditions.

Xin Nana N Lian Yongjian Y Lv Yongzheng Y Wang Yongjie Y Huang Xian-Qiang XQ Zhao Chang-Qiu CQ

RSC advances 20210719 40

An addition of H-phosphonates to aryl alkynes was realized under solvent- and metal-free conditions, affording Markovnikov-selective α-vinylphosphonates in moderate to good yields. A wide range of aryl alkynes could be applied for the reaction. A tentative mechanism of addition-substitution was proposed based on in situ 31P {1H} NMR studies. ...[more]

PMID: 35481042

Similar Datasets

Organobase-catalyzed 1,1-diborylation of terminal alkynes under metal-free conditions.

Project description:An organobase-catalyzed 1,1-diborylation of terminal alkynes from propargylic derivatives with bis(2,4-dimethylpentane-2,4-glycolato)diboron (B2oct2) is first reported, regioselectively providing 1,1-diborylalkene products with high efficiency. The catalytic pathway is well postulated on the basis of DFT calculations.

| S-EPMC9159348 | biostudies-literature

Recyclable heterogeneous metal foil-catalyzed cyclopropenation of alkynes and diazoacetates under solvent-free mechanochemical reaction conditions.

Project description:Silver and copper foil were found to be effective, versatile and selective heterogeneous catalysts for the cyclopropenation of terminal and internal alkynes under mechanochemical reaction conditions. This methodology enables the functionalization of a wide range of terminal or internal alkynes under ambient, aerobic, and solvent-free conditions. Finally, we have demonstrated a unique and versatile one-pot domino Sonogashira-cyclopropenation mechanochemical reaction for the formation of complex cyclopropenes.

| S-EPMC5969500 | biostudies-literature

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions.

Project description:Alkynyl selenides were synthesized by a straightforward one-pot and three-step methodology, without the need of diselenides as starting reagents, under an oxygen atmosphere and using PEG 200 as the solvent. This procedure involves the in situ generation of dialkyl diselenides through a K3PO4-assisted reaction of an alkyl selenocyanate obtained by a nucleophilic substitution reaction between KSeCN and alkyl halides. Successive reaction with terminal alkynes in the presence of t-BuOK affords the corresponding alkyl alkynyl selenide in moderate to good yields. Finally, this methodology allowed the synthesis of 2-alkylselanyl-substituted benzofuran and indole derivatives starting from convenient 2-substituted acetylenes.

| S-EPMC5480365 | biostudies-literature

Transition-Metal-Free Thioboration of Terminal Alkynes.

Project description:We present a new type of elementoboration reaction, the thioboration of terminal alkynes. This method enables highly controllable regio-/stereo-/chemoselective cis- and trans-thioboration on demand, affording synthetically versatile and densely functionalized vinyl boron/vinyl sulfide derivatives in a straightforward manner without the need for a transition-metal catalyst.

| S-EPMC11672135 | biostudies-literature

Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions.

Project description:The application of six novel α,β-dipeptides as chiral organocatalysts in the asymmetric Michael addition reaction between enolizable aldehydes and N-arylmaleimides or nitroolefins is described. With N-arylmaleimides as substrates, the best results were achieved with dipeptide 2 as a catalyst in the presence of aq. NaOH. Whereas dipeptides 4 and 6 in conjunction with 4-dimethylaminopyridine (DMAP) and thiourea as a hydrogen bond donor proved to be highly efficient organocatalytic systems in the enantioselective reaction between isobutyraldehyde and various nitroolefins.

| S-EPMC6152315 | biostudies-literature

Rhodium-Catalyzed Anti-Markovnikov Transfer Hydroiodination of Terminal Alkynes.

Project description:A rhodium-catalyzed anti-Markovnikov hydroiodination of aromatic and aliphatic terminal alkynes is reported. Depending on the choice of ligand and substrate, either (E)- or (Z)-configured alkenyl iodides are obtained in high to exclusive isomeric purity. The reaction exhibits a broad substrate scope and high functional group tolerance, employing easily accessible or commercially available aliphatic iodides as HI surrogates through a shuttle process. The synthesized vinyl iodides were applied in several C-C and C-heteroatom bond-forming reactions with full retention of the stereoselectivity. The developed method could be used to significantly shorten the total synthesis of a marine cis-fatty acid. Additionally, initial deuterium-labeling experiments and stoichiometric reactions shed some light on the potential reaction mechanism.

| S-EPMC10107805 | biostudies-literature

Silylative aromatization of p-quinone methides under metal and solvent free conditions.

Project description:A base-mediated silylation reaction leading to benzyl silanes has been developed. Under transition-metal and solvent free conditions, the silylation of a wide array of p-quinone methides is achieved using a Cs2CO3 catalyst in yields up to 96%. Carboxylation of the as-obtained organosilane with gaseous CO2 provides a new synthetic protocol for the preparation of carboxylic acid.

| S-EPMC9033227 | biostudies-literature

Microwave-induced electric discharges on metal particles for the synthesis of inorganic nanomaterials under solvent-free conditions.

Project description:Microwave irradiation of metals generates electric discharges (arcs). These arcs are used to generate nanoparticles of Cu and Ni and one-dimensional nanorods of CuS, ZnF2, and NiF2 protected with fluorinated amorphous carbon. We have also synthesized reduced graphene oxide and partially rolled graphene by this method.

| S-EPMC7372228 | biostudies-literature

Metal- and solvent-free synthesis of amides using substitute formamides as an amino source under mild conditions.

Project description:This study described an efficient and practical approach for amide synthesis. The reaction was conducted under metal- and solvent-free conditions at a mild temperature (40 °C) in air, and readily available formamides were used as an amino source. This reaction can be easily upgraded to the gram level with an excellent yield.

| S-EPMC6391388 | biostudies-literature

Stereospecific Synthesis of E-Alkenes through Anti-Markovnikov Hydroalkylation of Terminal Alkynes.

Project description:We have developed a method for stereospecific synthesis of E-alkenes from terminal alkynes and alkyl iodides. The hydroalkylation reaction is enabled by a cooperative action of copper and nickel catalysts and proceeds with excellent anti-Markovnikov selectivity. We demonstrate the broad scope of the reaction, which can be accomplished in the presence of esters, nitriles, aryl bromides, ethers, alkyl chlorides, anilines, and a wide range of nitrogen-containing heteroaromatic compounds. Mechanistic studies provide evidence that the copper catalyst activates the alkyne by hydrocupration, which controls both the regio- and diastereoselectivity of the overall reaction. The nickel catalyst activates the alkyl iodide and promotes cross coupling with the alkenyl copper intermediate.

| S-EPMC7304255 | 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