Phenazinium Salt-Catalyzed Aerobic Oxidative Amidation of Aromatic Aldehydes

Amides are prevalent in organic synthesis. Developing an efficient synthesis that avoids expensive oxidants and heating is highly desirable. Here the oxidative amidation of aromatic aldehydes is reported using an inexpensive metal-free visible light photocatalyst, phenazine ethosulfate, at low catal...

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Bibliographic Details
Published inOrganic letters Vol. 16; no. 21; pp. 5812 - 5815
Main Author Leow, Dasheng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.11.2014
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Amides - chemical synthesis
Amides - chemistry
Catalysis
Chemistry
Chemistry, Organic
Molecular Structure
Oxidation-Reduction
Phenazines - chemistry
Physical Sciences
Salts - chemistry
Science & Technology
ALCOHOLS
AMINES
LIGHT PHOTOREDOX CATALYSIS
ESTERIFICATION
PHOTOCHEMISTRY
5-METHYLPHENAZINIUM SALTS
AMIDE BOND FORMATION
SUCCINIC DEHYDROGENASE
PEPTIDE
AQUEOUS-SOLUTION
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Summary:Amides are prevalent in organic synthesis. Developing an efficient synthesis that avoids expensive oxidants and heating is highly desirable. Here the oxidative amidation of aromatic aldehydes is reported using an inexpensive metal-free visible light photocatalyst, phenazine ethosulfate, at low catalytic loading (1–2 mol %). The reaction proceeds at ambient temperature and uses air as the sole oxidant. The operationally easy procedure provides an economical, green, and mild alternative for the formation of amide bonds.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol5029354