Direct Amidation of Carboxylic Acids with Nitroarenes

N-Aryl amides are an important class of compounds in pharmaceutical and agrochemical chemistry. Rapid and low-cost synthesis of N-aryl amides remains in high demand. Herein, we disclose an operationally simple process to access N-aryl amides directly from readily available nitroarenes and carboxylic...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 84; no. 21; pp. 13922 - 13934
Main Authors Wang, Shao-Peng, Cheung, Chi Wai, Ma, Jun-An
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.11.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PEPTIDE COUPLING REAGENTS
SECONDARY AMIDES
AMINES
CHEMISTRY
ARYL
TRANSAMIDATION
INHIBITORS
AMINOCARBONYLATION
HYDROAMINATION
CADOGAN REACTION
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Summary:N-Aryl amides are an important class of compounds in pharmaceutical and agrochemical chemistry. Rapid and low-cost synthesis of N-aryl amides remains in high demand. Herein, we disclose an operationally simple process to access N-aryl amides directly from readily available nitroarenes and carboxylic acids as coupling substrates. This method involves the in situ activation of carboxylic acids to acyloxyphosphonium salt for one-pot amidation, without the need for isolation of the corresponding synthetic intermediates. Furthermore, the ease of preparation and workup allow the quick and efficient synthesis of a wide range of N-aryl amides, including several amide-based druglike and agrochemical molecules.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02068