Phosphite–imidazole catalyzed N -formylation and N -acylation of amines

A novel and convenient method for the N -formylation reaction of amines with DMF as a formylating agent has been developed, utilizing a catalytic amount of diethyl phosphite/imidazole. Diethyl phosphite, as a nucleophilic catalyst, plays a significant role in this conversion. The presented method ha...

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Published in:Organic & biomolecular chemistry 2023-10, Vol.21 (40), p.8182-8189
Main Authors: Kaboudin, Babak, Esfandiari, Hesam, Kakavand, Meysam, Sohrabi, Masoumeh, Yousefian Amirkhiz, Elahe, Neshat, Abdollah, Kawazoe, Teru, Fukaya, Haruhiko, Yanai, Hikaru
Format: Article
Language:English
Subjects:
Acetylation
Acylation
Amines
Benzimidazoles
Catalysts
Imidazole
Substrates
Sulfonamides
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Summary:A novel and convenient method for the N -formylation reaction of amines with DMF as a formylating agent has been developed, utilizing a catalytic amount of diethyl phosphite/imidazole. Diethyl phosphite, as a nucleophilic catalyst, plays a significant role in this conversion. The presented method has a broad substrate scope, and various N -formyl products were obtained in good to excellent yields. Moreover, by using DMA instead of DMF, the N -acetylation reaction was also successful. The reaction of o -phenylenediamines with DMF afforded the corresponding benzimidazoles. Furthermore, N -sulfonyl amidines were obtained in good to excellent yields by the reaction of sulfonamides with DMF under similar conditions.
ISSN:1477-0520
1477-0539
DOI:10.1039/D3OB01306E