HFIP-Promoted Aromatic Electrophilic Amidation of Indoles and Pyrroles with Isocyanates

A mild and practical method for synthesizing amidoindoles and amidopyrroles was described via the direct amidation of indoles or pyrroles with isocyanates promoted by 1,1,1,3,3,3-hexafluoroisopropanol (HFIP). In this reaction, HFIP acted as a strong hydrogen bond-donating solvent to activate isocyanates, enabling the amidation of electron-rich nitrogen-containing heterocycles.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-03-19
DOI
https://doi.org/10.1021/acs.joc.4c03176
Citations
2
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
1.61

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article

HFIP-Promoted Aromatic Electrophilic Amidation of Indoles and Pyrroles with Isocyanates

Liang-Bi Chen, Chao Li, Jiaxing Li, Song Song et al.
2 citations
The Journal of Organic Chemistry
Chemical Synthesis and Analysis
1.61
article

HFIP-Promoted Aromatic Electrophilic Amidation of Indoles and Pyrroles with Isocyanates

Liang-Bi Chen, Chao Li, Jiaxing Li, Song Song, Hongye Wang
article en
2 citations

Abstract

A mild and practical method for synthesizing amidoindoles and amidopyrroles was described via the direct amidation of indoles or pyrroles with isocyanates promoted by 1,1,1,3,3,3-hexafluoroisopropanol (HFIP). In this reaction, HFIP acted as a strong hydrogen bond-donating solvent to activate isocyanates, enabling the amidation of electron-rich nitrogen-containing heterocycles.

The Journal of Organic ChemistryVol. 90(12)
Peking University (CN)
National Natural Science Foundation of China, Peking University
Openalex Percentile: Top 18%
Chemical Synthesis and Analysis
1.61
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