Electrochemically Induced Intermolecular Cross-Dehydrogenative C–O Coupling of β‑Diketones and β‑Ketoesters with Carboxylic Acids

The electrochemically induced cross-dehydrogenative C–O coupling of β-diketones and β-ketoesters (C–H reagents) with carboxylic acids (O–H reagents) was developed. An important feature of this reaction lies in the selective formation of intermolecular C–O coupling products in high yields, up to 92%,...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 84; no. 3; pp. 1448 - 1460
Main Authors Bityukov, Oleg V, Matveeva, Olesya K, Vil’, Vera A, Kokorekin, Vladimir A, Nikishin, Gennady I, Terent’ev, Alexander O
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.02.2019
Amer Chemical Soc
Subjects
carbon
carboxylic acids
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
dimethyl sulfoxide
electric current
electrochemistry
electrodes
organic chemistry
oxidants
Physical Sciences
platinum
Science & Technology
solvents
ANTIFUNGAL MICONAZOLE ACTIVITY
ELECTROORGANIC CHEMISTRY
REAGENT
KETO-ESTERS
REDUCTION
DICARBONYL COMPOUNDS
CARBONYL-COMPOUNDS
BOND FORMATION
ENANTIOSELECTIVE ALPHA-HYDROXYLATION
ANODIC-OXIDATION
Online AccessGet full text

Cover

More Information
Summary:The electrochemically induced cross-dehydrogenative C–O coupling of β-diketones and β-ketoesters (C–H reagents) with carboxylic acids (O–H reagents) was developed. An important feature of this reaction lies in the selective formation of intermolecular C–O coupling products in high yields, up to 92%, using DMSO as a solvent with a broad substrate scope in an undivided cell equipped with carbon and platinum electrodes at high current density. Electric current acts as a stoichiometric oxidant.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.8b02791