Exploring the mechanism of the reductive amination of acetophenones the Borch approach: the role of the acid catalyst

The energetic viability of several mechanistic variations of the reductive amination of acetophenones via the Borch approach was re-examined through density functional theory calculations. The crucial involvement of the acid catalyst is evident not only in the elimination of water, but also in the i...

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Published in:Organic & biomolecular chemistry 2024-05, Vol.22 (19), p.3926-3932
Main Authors: Souza, João P. A, Jacobs, Amanda K, Piovan, Leandro, Campos, Renan B
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Summary:The energetic viability of several mechanistic variations of the reductive amination of acetophenones via the Borch approach was re-examined through density functional theory calculations. The crucial involvement of the acid catalyst is evident not only in the elimination of water, but also in the initial nucleophilic step. This role increases with the electron-donating capability of the substituent positioned at the para -position of acetophenone. In the reductive amination process, the acid catalyst plays a crucial role not only in the elimination of water but also in the nucleophilic step, particularly when electron-donating groups are installed at the para-position of the acetophenone.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00160e