Organo-cyanamides: convenient reagents for catalytic amidation of carboxylic acids

An unprecedented DMAP-catalysed amidation of aryl and alkyl carboxylic acids with organo-cyanamides has been developed. Unlike the use of N -cyano- N -phenyl- p -methylbenzenesulfonamide (NCTS) as an electrophilic cyanating reagent, an unusual desulfonylation/decyanation reaction model has been disc...

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Published inChemical communications (Cambridge, England) Vol. 59; no. 4; pp. 438 - 441
Main Authors Li, Li-Jing, Zhou, Zhong-Qiang, Liu, Zi-Kui, He, Yuan-Yuan, Jia, Feng-Cheng, Hu, Xiao-Qiang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 05.01.2023
Royal Society of Chemistry
Subjects
Amides
Carboxylic Acids
Chemistry
Chemistry, Multidisciplinary
Cyanamide
Cyanamides
Indicators and Reagents
Molecular Structure
Physical Sciences
Reagents
Science & Technology
Substrates
ALCOHOLS
AMIDE BOND FORMATION
COUPLING REAGENTS
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Summary:An unprecedented DMAP-catalysed amidation of aryl and alkyl carboxylic acids with organo-cyanamides has been developed. Unlike the use of N -cyano- N -phenyl- p -methylbenzenesulfonamide (NCTS) as an electrophilic cyanating reagent, an unusual desulfonylation/decyanation reaction model has been disclosed for the first time. Remarkable features of this reaction include readily available substrates, simple operation and broad scope, enabling the efficient synthesis of structurally diverse amides. The synthetic utility of this protocol was demonstrated by the late-stage amidation of bioactive carboxylic acids and a scale-up reaction. An unprecedented DMAP-catalysed amidation of aryl and alkyl carboxylic acids with organo-cyanamides has been developed for the first time, enabling the efficient synthesis of a range of structurally diverse amides in useful to good yields.
Bibliography:https://doi.org/10.1039/d2cc05826j
Electronic supplementary information (ESI) available. See DOI
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc05826j