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. 2020 Feb 26;25(5):1040.
doi: 10.3390/molecules25051040.

Solvent-Free Iron(III) Chloride-Catalyzed Direct Amidation of Esters

Blessing D Mkhonazi  1 , Malibongwe Shandu  1 , Ronewa Tshinavhe  1 , Sandile B Simelane  2 , Paseka T Moshapo  1
Affiliations

Solvent-Free Iron(III) Chloride-Catalyzed Direct Amidation of Esters

Blessing D Mkhonazi et al. Molecules. .

Abstract

Amide functional groups are prominent in a broad range of organic compounds with diverse beneficial applications. In this work, we report the synthesis of these functional groups via an iron(iii) chloride-catalyzed direct amidation of esters. The reactions are conducted under solvent-free conditions and found to be compatible with a range of amine and ester substrates generating the desired amides in short reaction times and good to excellent yields at a catalyst loading of 15 mol%.

Keywords: amidation; amides; esters; iron(III) chloride; solvent-free.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Catalyst = AlCl3, FeCl3, FeCl2, FeBr3 or BiCl3.
Figure 1
Figure 1
Reaction optimization. N.D. = Not Detected.
Scheme 2
Scheme 2
a Reaction mixture solidified and 0.5 mL CH3CN was added.
Scheme 3
Scheme 3
General reaction scheme for FeCl3 substrate scope evaluation. a Reaction mixture solidified and 0.5 mL of CH3CN was added.
Scheme 4
Scheme 4
Lactam synthesis.
Scheme 5
Scheme 5
Application of the developed protocol in the synthesis of anti-TB pyrimidine carboxamides.
See this image and copyright information in PMC

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