N‑Heterocyclic Carbene-Mediated Microfluidic Oxidative Electrosynthesis of Amides from Aldehydes

A flow process for N-Heterocyclic Carbene (NHC)-mediated anodic oxidative amidation of aldehydes is described, employing an undivided microfluidic electrolysis cell to oxidize Breslow intermediates. After electrochemical oxidation, the reaction of the intermediate N-acylated thiazolium cation with p...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 5; pp. 1198 - 1201
Main Authors Green, Robert A, Pletcher, Derek, Leach, Stuart G, Brown, Richard C. D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.03.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
CATALYSIS
AMINES
ESTERS
AMIDATION
COUPLING REAGENTS
BOND FORMATION
CELL
ORGANOCATALYZED ANODIC-OXIDATION
CARBOXYLIC-ACIDS
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Summary:A flow process for N-Heterocyclic Carbene (NHC)-mediated anodic oxidative amidation of aldehydes is described, employing an undivided microfluidic electrolysis cell to oxidize Breslow intermediates. After electrochemical oxidation, the reaction of the intermediate N-acylated thiazolium cation with primary amines is completed by passage through a heating cell to achieve high conversion in a single pass. The flow mixing regimen circumvented the issue of competing imine formation between the aldehyde and amine substrates, which otherwise prevented formation of the desired product. High yields (71–99%), productivities (up to 2.6 g h–1), and current efficiencies (65–91%) were realized for 19 amides.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00339