Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A novel and highly efficient esterification process using triphenylphosphine oxide with oxalyl chloride.

ABSTRACT: Triphenylphosphine oxide (TPPO) and oxalyl chloride ((COCl)2) are used as novel and high-efficiency coupling reagents for the esterification of alcohols with carboxylic acids via the TPPO/(COCl)2 system at room temperature for 1?h. The reaction represents the first TPPO-promoted esterification under mild and neutral conditions with excellent yields. Furthermore, we proposed a plausible mechanism with the help of 31P NMR spectroscopy.

SUBMITTER: Jia M

PROVIDER: S-EPMC5830786 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

A novel and highly efficient esterification process using triphenylphosphine oxide with oxalyl chloride.

Jia Mingzhu M Jiang Lixue L Niu Fanfan F Zhang Yu Y Sun Xiaoling X

Royal Society open science 20180221 2

Triphenylphosphine oxide (TPPO) and oxalyl chloride ((COCl)2) are used as novel and high-efficiency coupling reagents for the esterification of alcohols with carboxylic acids via the TPPO/(COCl)2 system at room temperature for 1 h. The reaction represents the first TPPO-promoted esterification under mild and neutral conditions with excellent yields. Furthermore, we proposed a plausible mechanism with the help of 31P NMR spectroscopy. ...[more]

PMID: 29515897

Similar Datasets

Removal of Triphenylphosphine Oxide by Precipitation with Zinc Chloride in Polar Solvents.

Project description:While the use of triphenylphosphine as a reductant is common in organic synthesis, the resulting triphenylphosphine oxide (TPPO) waste can be difficult to separate from the reaction product. While a number of strategies to precipitate TPPO are available, none have been reported to work in more polar solvents. We report here that mixing ZnCl2 with TPPO precipitates a TPPO-Zn complex in high yield in several common polar organic solvents. The solvent compatibility of this procedure and the reliability of the precipitation in the presence of polar functional groups were examined to show the utility and limitations of this method.

| S-EPMC5634519 | biostudies-literature

Triphenylphosphine Dibromide: A Simple One-pot Esterification Reagent.

Project description:We report a one-pot, expedient protocol for the conversion of carboxylic acids to their esters using excess triphenylphosphine dibromide, base, and the alcohol. The reaction gave the esterified product in moderate-to-high yields (30-95%). For chiral acids, the reaction proceeded with little or no racemization. Use of a chiral alcohol in this transformation gave the ester with retention of configuration of the stereogenic center. Information is presented indicating that esterification proceeds through the intermediate generation of an acyloxyalkoxyphosphorane and where steric interactions play an important role in the energetics of the reaction.

| S-EPMC2633481 | biostudies-literature

Solvate-free bis-(triphenylphosphine)iminium chloride.

Project description:The title compound, C(36)H(30)NP(2) (+)·Cl(-), crystallized in the solvate-free form from a CH(3)CN/OEt(2) solution. The chloride anion and the N atom of the [(Ph(3)P)(2)N](+) cation are located on a twofold axis, yielding overall symmetry 2 for the cation. The central P-N-P angle [133.0?(3)°] is at the low end of the range of observed P-N-P angles.

| S-EPMC3011587 | biostudies-literature

Solvent-Free Esterification of Carboxylic Acids Using Supported Iron Oxide Nanoparticles as an Efficient and Recoverable Catalyst.

Project description:Supported iron oxide nanoparticles on mesoporous materials (FeNP@SBA-15) have been successfully utilized in the esterification of a variety carboxylic acids including aromatic, aliphatic, and long-chain carboxylic acids under convenient reaction conditions. The supported catalyst could be easily recovered after reaction completion and reused several times without any loss in activity after up to 10 runs.

| S-EPMC5456927 | biostudies-other

Cationic 1,2-Azaborine Adducts of Trimethylphosphine, Triphenylphosphine oxide, and Pyridine-N-oxide.

Project description:The first cationic 1,2-azaborine adducts of neutral phosphorous- and oxygen-based nucleophiles have been synthesized and characterized via spectroscopic and single crystal X-ray diffraction analysis.

| S-EPMC3027061 | biostudies-literature

One-Step Solution-Immersion Process of Hydrophobic Octyl Graphene Oxide-Modified Nickel Foam for Highly Efficient Oil-Water Separation.

Project description:Hydrophobic foam was prepared by immersing nickel foam in a dispersion of octyl group-grafted graphene oxide (GO) and used to clean up oil-water mixtures. Octyl graphene oxide (C8-GO) was synthesized using GO and triethoxyoctylsilane by a solvothermal method. The resulting coverage of the foam was characterized, and the surface morphology of the foam was also investigated. The static water contact angle (SWCA) was measured to evaluate the change in wettability of the developed foam. The pristine smooth microstructure of the nickel foam became rough after being covered with the C8-GO nanosheets. The SWCA of C8-GO nickel foam (C8-GO NF) surface was approximately 147°. The C8-GO NF can float on the surface of the water in contrast to the easy-sinking unmodified foam, demonstrating good hydrophobicity. Furthermore, the C8-GO NF showed outstanding performance in organic compound adsorption and excellent efficiency in oil-water separation. The reusability and durability of the obtained foam are evaluated to highlight its usability in more complicated scenarios. The use of C8-GO NF was proved to be a promising strategy for oil-water separation under harsh circumstance.

| S-EPMC6964511 | biostudies-literature

Mild deprotection of the N-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride.

Project description:We report a mild method for the selective deprotection of the N-Boc group from a structurally diverse set of compounds, encompassing aliphatic, aromatic, and heterocyclic substrates by using oxalyl chloride in methanol. The reactions take place under room temperature conditions for 1-4 h with yields up to 90%. This mild procedure was applied to a hybrid, medicinally active compound FC1, which is a novel dual inhibitor of IDO1 and DNA Pol gamma. A broader mechanism involving the electrophilic character of oxalyl chloride is postulated for this deprotection strategy.

| S-EPMC7810210 | biostudies-literature

Green and Efficient Esterification Method Using Dried Dowex H+/NaI Approach.

Project description:The usefulness of dried Dowex H+ cation-exchange resin with or without sodium iodide (NaI) as a catalyst system for different kinds of esterifications using carboxylic acids and alcohols as starting materials has been systematically investigated. The Dowex H+/NaI approach is very effective, generally high yielding, energy-efficient, and nontoxic, and the Dowex H+ resin is reusable. Since the whole procedure from start to product isolation is also very simple, these features make the method environmentally friendly. The method is regioselective, and its potential for separation of valuable carboxylic acids like resin acids from mixtures containing other kinds of carboxylic acids has been demonstrated. Examples for green and straightforward esterification of highly important natural amino acids are also presented.

| S-EPMC6648282 | biostudies-literature

A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide-Triflic Acid Catalysis.

Project description:Following our discovery that silver(I) oxide-promoted glycosylation with glycosyl bromides can be greatly accelerated in the presence of catalytic TMSOTf or TfOH, we report herein a new discovery that glycosyl chlorides are even more effective glycosyl donors under these reaction conditions. The developed reaction conditions work well with a variety of glycosyl chlorides. Both benzoylated and benzylated chlorides have been successfully glycosidated, and these reaction conditions proved to be effective in coupling substrates containing nitrogen and sulfur atoms. Another convenient feature of this glycosylation is that the progress of the reaction can be monitored visually; its completion can be judged by the disappearance of the characteristic dark color of Ag2 O.

| S-EPMC7695998 | biostudies-literature

Nitrogen-Mediated Graphene Oxide Enables Highly Efficient Proton Transfer.

Project description:Two-dimensional (2D) graphene and graphene oxide (GO) offer great potential as a new type of cost-efficient proton-exchange membranes (PEM) for electrochemical devices. However, fundamental issues of proton transfer mechanism via 2D membranes are unclear and the transfer barrier for perfect graphene are too high for practical application. Using ab initio molecular dynamic simulations, we screened the proton transfer barrier for different un-doped and nitrogen doped GO membranes, and clarified the corresponding transfer mechanisms. More significantly, we further identify that N-mediated GO can be built into a highly efficient PEM with a proton transfer rate of seven orders of magnitude higher than an un-doped case via. a proton relay mechanism between a ketone-like oxygen and a pyridine-like nitrogen across the vacancy site. The N-doped 2D GO is also impermeable to small molecules, and hence a highly efficient PEM for practical applications.

| S-EPMC5507853 | biostudies-other

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