Synthesis of Trifluoroacetamidoketones by Acylation of Ferrocene with In Situ Protected Amino Acids

The Friedel-Crafts acylation of ferrocene with amino acids carried out under mild conditions (metal-free catalytic system, room temperature, and a short reaction time of 1 h) has been reported. The acylating agent is generated in situ by N-protection of the amino group of the amino acid, followed by formation of mixed anhydride. This one-pot triflic-acid-promoted reaction provides <i>N</i>-trifluoroacetyl-protected amidoketones in good to excellent yields. Moreover, the trifluoroacetyl group can be easily removed or replaced with another protecting group under mild conditions in a one-pot procedure.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-02-18
DOI
https://doi.org/10.1021/acs.joc.4c02717
Citations
2
Primary Topic
Ferrocene Chemistry and Applications
Type
article
Field-Weighted Citation Impact
1.87

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article

Synthesis of Trifluoroacetamidoketones by Acylation of Ferrocene with In Situ Protected Amino Acids

Anna Makal, Michał Piotrowicz, Bogna Rudolf, Róża Dziewiątkowska et al.
2 citations
The Journal of Organic Chemistry
Ferrocene Chemistry and Applications
1.87
article

Synthesis of Trifluoroacetamidoketones by Acylation of Ferrocene with In Situ Protected Amino Acids

Anna Makal, Michał Piotrowicz, Bogna Rudolf, Róża Dziewiątkowska, Natasza Masłowska
article en
2 citations

Abstract

The Friedel-Crafts acylation of ferrocene with amino acids carried out under mild conditions (metal-free catalytic system, room temperature, and a short reaction time of 1 h) has been reported. The acylating agent is generated in situ by N-protection of the amino group of the amino acid, followed by formation of mixed anhydride. This one-pot triflic-acid-promoted reaction provides <i>N</i>-trifluoroacetyl-protected amidoketones in good to excellent yields. Moreover, the trifluoroacetyl group can be easily removed or replaced with another protecting group under mild conditions in a one-pot procedure.

The Journal of Organic ChemistryVol. 90(8)
University of Łódź (PL), University of Warsaw (PL)
Narodowe Centrum Nauki, Uniwersytet Łódzki
Openalex Percentile: Top 18%
Ferrocene Chemistry and Applications
1.87
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