Electrosynthesis of 2‐Arylpropionic Acids from α‐Methylbenzyl Chlorides and Carbon Dioxide by [Co(Salen)]

doi:10.1081/SCC-200054748

Paper

Electrosynthesis of 2‐Arylpropionic Acids from α‐Methylbenzyl Chlorides and Carbon Dioxide by [Co(Salen)]

Published May 1, 2005 · J. Damodar, S. Krishna Mohan, S. K. Khaja Lateef

Synthetic Communications

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15

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Abstract

Abstract The electrochemical synthesis of the 2‐arylpropionic acid group of nonsteroidal anti‐inflammatory agents such as ibuprofen, naproxen, indoprofen, biprofen, cicloprofen, and fenoprofen has been carried out in dimethylformamide (DMF) containing tetra‐n‐butylammonium perchlorate (nBu4NClO4) by electrochemical carboxylation of α‐methylbenzyl chlorides catalyzed by a schiff‐base complex [Co(salen)] in an undivided cell equipped with a platinum cathode and magnesium anode under constant current density of 10 mA/cm2 in good yields. Cyclic voltammetric studies have also been carried out to investigate the mechanism by which [Co(salen)] catalyzes the cathodic reaction of α‐methylbenzyl chlorides in presence of CO2 by taking α‐phenylethylchloride as the model compound.

Study Snapshot

Electrochemical synthesis of 2'-arylpropionic acids from methylbenzyl chlorides and carbon dioxide can produce nonsteroidal anti-inflammatory agents like ibuprofen, naproxen, and others.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Electrosynthesis of 2‐Arylpropionic Acids from α‐Methylbenzyl Chlorides and Carbon Dioxide by [Co(Salen)]

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References

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Electrochemical carboxylation of benzylchlorides with Pd(II) complex under atmospheric pressure produces 2-arylpropionic acids in good yields, with reduced palladium species playing a cooperative role in carbon dioxide activation.

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Electrocatalytic reduction of benzal chloride to stilbene 12 involves a sequence involving electrocatalytic conversion of benzal chloride to a mixture of 1,2-dichloro-1,2-diphenylethanes, followed by electrocatalytic conversion of the latter to 12.

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This one-pot synthesis of ibuprofene involves three consecutive steps of superbase metalation, leading to 2-(4-isobutylphenyl)propanoic acid with 52% overall yield.

Electrochemical carboxylation of benzal chloride

Electrochemical carboxylation of benzal chloride in diaphragmless cells with aluminium sacrificial anodes can yield up to 50% and 30% of phenylmalonic acid, with phenylacetic acid always present.

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This study demonstrates the successful synthesis of 2-[4-(1-Oxo-2-isoindolinyl)phenyl]propanoic acid, a potent analgesic and anti-inflammatory agent, using three methods and cinchonidine as a resolution reagent.

Citations

Use of CO2 for Electrosynthesis

Electrochemical processes can reduce CO2 emissions and produce valuable fuels and chemicals, with ionic liquids playing a key role as ideal solvents and electrolytes.

Electrochemical Tuning of CO2 Reactivity in Ionic Liquids Using Different Cathodes: From Oxalate to Carboxylation Products

Copper cathode and ionic liquids as electrolytes offer a cheaper and greener alternative for activating carbon dioxide, with cyano derivatives allowing for tuning of reactivity.

Silver encapsulated copper salen complex: efficient catalyst for electrocarboxylation of cinnamyl chloride with CO2

The [Cu]@Ag composite catalyst effectively catalyzes the electrocarboxylation of cinnamyl chloride with CO2, yielding,-unsaturated carboxylic acids with moderate selectivity.

Electrocarboxylation of halobenzonitriles: An environmentally friendly synthesis of phthalate derivatives

Electrochemical techniques using CO2 as a building block can efficiently produce valuable compounds like aromatic acids and phthalate derivatives, offering a greener approach for plastic polymer production.

Electrocarboxylation of 1-chloro-(4-isobutylphenyl)ethane with a silver cathode in ionic liquids: an environmentally benign and efficient way to synthesize Ibuprofen

This study presents a greener, efficient method for synthesizing Ibuprofen using CO2 as a C1-organic building block, with high yields and conversion ratios, in mild conditions.