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Base-catalyzed synthesis of aryl amides from aryl azides and aldehydes
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0003-1121-4007
2016 (English)In: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 7, no 1, 713-718 p.Article in journal (Refereed) Published
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Text
Abstract [en]

Aryl amides have been used as important compounds in pharmaceuticals, materials and in molecular catalysis. The methods reported to prepare aryl amides generally require very specific reagents, and the most popular carboxyl-amine coupling reactions demand stoichiometric activators. Herein, we report that aryl azides react with aldehydes under base-catalyzed conditions to yield aryl amides efficiently. Mechanistic investigations support the formation of triazoline intermediates via azide-enolate cycloaddition, which subsequently undergo rearrangement to give amides by either thermal decomposition (20-140 degrees C) or aqueous acid work-up at room temperature. The strategy does not require nucleophilic anilines and is especially efficient for highly electron-deficient aryl amides, including perfluoroaryl amides, which are otherwise challenging to synthesize.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2016. Vol. 7, no 1, 713-718 p.
Keyword [en]
REGIOSELECTIVE SYNTHESIS, MEDIATED AMIDATION, CARBONYL-COMPOUNDS, SECONDARY AMIDES, C(SP(3))-H BONDS, ROOM-TEMPERATURE, CARBOXYLIC-ACIDS, ALKYL AZIDES, ARYLATION, AMINES
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-180586DOI: 10.1039/c5sc03510dISI: 000366826900087Scopus ID: 2-s2.0-84951154431OAI: oai:DiVA.org:kth-180586DiVA: diva2:896608
Note

QC 20160121

Available from: 2016-01-21 Created: 2016-01-19 Last updated: 2017-03-03Bibliographically approved

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CiteExportLink to record
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