TiF4-catalyzed direct amidation of carboxylic acids and amino acids with amines

Unlike other metal fluorides, catalytic titanium tetrafluoride enhances the direct amidation of aromatic and aliphatic carboxylic acids and N-protected amino acids in refluxing toluene. While aromatic acids were converted to amides with 10 mol% of the catalyst within 24 h, aliphatic acids underwent...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 22; no. 9; pp. 1915 - 1919
Main Authors Alawaed, Abdulkhaliq A., Ramachandran, P. Veeraraghavan
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.02.2024
Royal Society of Chemistry
Subjects
Aliphatic compounds
Amides
Amines
Amino acids
Carboxylic acids
Catalysts
Chemistry
Chemistry, Organic
Metal fluorides
Peptides
Physical Sciences
Refluxing
Science & Technology
Titanium
Toluene
AMIDE FORMATION
CATALYZED N-FORMYLATION
HEXAFLUOROPHOSPHATE
TIF4
BOND
PEPTIDE
COUPLING REAGENT
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Summary:Unlike other metal fluorides, catalytic titanium tetrafluoride enhances the direct amidation of aromatic and aliphatic carboxylic acids and N-protected amino acids in refluxing toluene. While aromatic acids were converted to amides with 10 mol% of the catalyst within 24 h, aliphatic acids underwent a faster reaction (12 h), with lower catalyst loading (5 mol%). This protocol is equally efficient with alkyl and aryl amines providing a variety of carboxamides and peptides in 60-99% yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01943h