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Issue 31, 2018
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Alternative formation of amides and β-enaminones from aroyl chlorides using the TiCl4-trialkylamine reagent system

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Abstract

The TiCl4/NR3 reagent system has been successfully employed for the synthesis of amides and β-enaminones. The reaction of variously substituted benzoyl chlorides with the TiCl4/NR3 reagent system, by using two different experimental procedures (Method A and Method B), afforded alternatively the corresponding amides and β-enaminones as unique or major products. The two developed protocols were investigated with a series of tertiary amines. The reactions, modulated by the presence of TiCl4, provided the corresponding amides or β-enaminones with satisfactory yields. This paper reports a new method for carbon–carbon bond formation via the reaction of aroyl chlorides with the TiCl4/NR3 reagent system.

Graphical abstract: Alternative formation of amides and β-enaminones from aroyl chlorides using the TiCl4-trialkylamine reagent system

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Supplementary files

Article information


Submitted
29 Jun 2018
Accepted
20 Jul 2018
First published
23 Jul 2018

Org. Biomol. Chem., 2018,16, 5677-5683
Article type
Paper

Alternative formation of amides and β-enaminones from aroyl chlorides using the TiCl4-trialkylamine reagent system

A. Leggio, A. Comandè, E. L. Belsito, M. Greco, L. Lo Feudo and A. Liguori, Org. Biomol. Chem., 2018, 16, 5677
DOI: 10.1039/C8OB01536H

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