Mechanochemical Unlocking of Phthalimide Transamidation: A Path to N-Substituted Phthalamides

The transamidation (aminolysis) of phthalimide with primary and secondary aliphatic amines is reported, where reactivity is induced by mechanical forces without the need for catalysts, acids, or thermal activation. The reaction proceeds at room temperature to afford <i>N</i>-substituted phthalamides as the major products. It is carried out in a mixer mill using stainless-steel jars and balls. The scope is demonstrated with more than 20 examples, achieving yields of up to 98%.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-09-25
DOI
https://doi.org/10.1021/acs.joc.5c01647
Primary Topic
Chemical Synthesis and Analysis
Type
article
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article

Mechanochemical Unlocking of Phthalimide Transamidation: A Path to N-Substituted Phthalamides

Carsten Bolm, Diego Gamba‐Sánchez, Camilo Morales-Manrique
The Journal of Organic Chemistry
Chemical Synthesis and Analysis
article

Mechanochemical Unlocking of Phthalimide Transamidation: A Path to N-Substituted Phthalamides

Carsten Bolm, Diego Gamba‐Sánchez, Camilo Morales-Manrique
article en

Abstract

The transamidation (aminolysis) of phthalimide with primary and secondary aliphatic amines is reported, where reactivity is induced by mechanical forces without the need for catalysts, acids, or thermal activation. The reaction proceeds at room temperature to afford <i>N</i>-substituted phthalamides as the major products. It is carried out in a mixer mill using stainless-steel jars and balls. The scope is demonstrated with more than 20 examples, achieving yields of up to 98%.

The Journal of Organic ChemistryVol. 90(39)
Universidad de Los Andes (CO), Laboratoire de Synthèse Organique (FR), RWTH Aachen University (DE)
Openalex Percentile: Top 77%
Chemical Synthesis and Analysis
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