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Issue 31, 2019
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Formamide catalyzed activation of carboxylic acids – versatile and cost-efficient amidation and esterification

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Abstract

A novel, broadly applicable method for amide C–N and ester C–O bond formation is presented based on formylpyrrolidine (FPyr) as a Lewis base catalyst. Herein, trichlorotriazine (TCT), which is the most cost-efficient reagent for OH-group activation, was employed in amounts of ≤40 mol% with respect to the starting material (100 mol%). The new approach is distinguished by excellent cost-efficiency, waste-balance (E-factor down to 3) and scalability (up to >80 g). Moreover, high levels of functional group compatibility, which includes acid-labile acetals and silyl ethers, are demonstrated and even peptide C–N bonds can be formed. In comparison to reported amidation procedures using TCT, yields are considerably improved (for instance from 26 to 91%) and esterification is facilitated for the first time in synthetically useful yields. These significant enhancements are rationalized by activation by means of acid chlorides instead of less electrophilic acid anhydride intermediates.

Graphical abstract: Formamide catalyzed activation of carboxylic acids – versatile and cost-efficient amidation and esterification

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Supplementary files

Article information


Submitted
01 May 2019
Accepted
16 Jun 2019
First published
17 Jun 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 7399-7406
Article type
Edge Article

Formamide catalyzed activation of carboxylic acids – versatile and cost-efficient amidation and esterification

P. H. Huy and C. Mbouhom, Chem. Sci., 2019, 10, 7399
DOI: 10.1039/C9SC02126D

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