Catalytic methyl transfer from dimethylcarbonate to carboxylic acids.

doi:10.1021/jo401941v

Paper

Catalytic methyl transfer from dimethylcarbonate to carboxylic acids.

Published Nov 4, 2013 · Yuan-Zhao Ji, Jessica Sweeney, Jillian Zoglio

The Journal of organic chemistry

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31

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Abstract

Although methylation reactions are commonplace, currently used reagents are hazardous, toxic, and/or unstable. Dimethylcarbonate has been put forth as an inexpensive, nontoxic, and "green" potential methylating reagent. Herein we report a general, base-catalyzed methyl transfer from dimethylcarbonate to carboxylic acids. High selectivity for esterification is observed even in the presence of unprotected phenols, and the mild reaction conditions enable conservation of stereochemistry at epimerizable stereocenters. Isotope-labeling studies suggest a mechanism proceeding by direct methyl transfer from dimethylcarbonate to the substrate.

Study Snapshot

Dimethylcarbonate shows potential as an inexpensive, nontoxic, and green methylating reagent, with high selectivity for esterification and preservation of stereochemistry at epimerizable stereocenters.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Catalytic methyl transfer from dimethylcarbonate to carboxylic acids.

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References

Upgrading of Levulinic Acid with Dimethylcarbonate as Solvent/Reagent

Levulinic acid reacts with dimethylcarbonate to produce methyl levulinate, dimethyl succinate, and related products, with control over selectivity achieved by tuning reaction conditions.

Enzyme catalyzed transesterification of waste cooking oil with dimethyl carbonate

Biodiesel can be successfully produced from waste cooking oil and dimethyl carbonate using enzyme-catalyzed transesterification, with a maximum conversion of 77.87% achieved under optimal conditions.

Methyl esterification of carboxylic acids with dimethyl carbonate promoted by K2CO3/tetrabutylammonium chloride

This green process using K2CO3 and tetrabutylammonium chloride promotes the esterification of carboxylic acids with dimethyl carbonate, resulting in high yield and purity of methyl esters.

Enantioselective total synthesis of (+)-reserpine.

This study presents a catalytic, enantioselective synthesis of (+)-reserpine using a highly diastereoselective, chiral catalyst-controlled formal aza-Diels-Alder reaction, addressing the challenge of setting the C3 stereo

One-step synthesis of racemic α-amino acids from aldehydes, amine components, and gaseous CO2 by the aid of a bismetal reagent.

This study successfully achieved a one-step synthesis of racemic -amino acids from aldehydes, amine components, and gaseous CO2 in a single operation, enabling the synthesis of a wide range of racemic arylglycine derivatives in high yields.

Citations

Substrate-Induced Cooperative Ionic Catalysis: Difunctionalization of Indole Derivatives Employing Dimethyl Carbonate.

Dimethyl carbonate (DMC) can act as both a nucleophilic and electrophilic precursor, enabling environmentally benign strategies for indole derivatives.

Sustainable C-H Methylation Employing Dimethyl Carbonate.

Dimethyl carbonate (DMC) offers sustainable and biocompatible chemistry for C-H methylation reactions, offering new opportunities and challenges for research across disciplines.

Direct Synthesis of Dimethyl Carbonate from CO2: From the Perspective of Dimethyl-Carbonate, A Promising Material for the Future

Direct synthesis of dimethyl carbonate from CO2 shows potential for carbon capture and utilization and storage, with lower DMC selling prices and catalyst deactivation issues potentially advancing the technology.

Performance and kinetics investigations on the CeO2 catalyzed direct synthesis of dimethyl carbonate from CO2 and methanol in dual supercritical conditions

Flower CeO2 catalysts show the highest catalytic performance for the direct synthesis of dimethyl carbonate from CO2 and methanol under dual supercritical conditions, with a maximum yield of 3.11 mmol/g cat.

Ceria nanostructured catalysts for conversion of methanol and carbon dioxide to dimethyl carbonate

CeO2 nanorod catalysts produce the highest dimethyl carbonate yield, with nanooctahedra and nanocubes showing moderate activity, while the reusability of the catalysts is relatively stable.

Recent Advances in Methylation: A Guide for Selecting Methylation Reagents.

Recent advances in methylation chemistry provide chemists with a wide range of reagents, increasing flexibility in synthetic route planning.

Applications of Dimethyl Carbonate for the Chemical Upgrading of Biosourced Platform Chemicals

Dimethyl carbonate (DMC) is a versatile, nontoxic compound that can be used to efficiently convert biosourced substrates into added-value compounds using sustainable protocols and safe reagents.

Unprecedented alkylation of carboxylic acids by boron trifluoride etherate

Boron trifluoride etherate effectively alkylates both aromatic and aliphatic carboxylic acids in short reaction times, with good yields and compatibility with various functional groups.