Article | REF: CHV2210 V1

Usage of 1.3 dicarbonyl derivatives in domino and multicomponent reactions

Authors: Damien BONNE, Thierry CONSTANTIEUX, Yoann COQUEREL, Jean RODRIGUEZ

Publication date: May 10, 2010, Review date: October 17, 2017

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ABSTRACT

Covalent linkages, i.e. that link two atoms by associating their respective electrons, are essential elements in physics and chemistry. Indeed, such linkages are at the origin of the construction of molecules (one or more covalent linkage created in one operation by the reaction between several substrates). Certain characteristics of these linkages have led to differentiations; a reaction is called domino when a minimum of two covalent linkages are created. Where a minimum of three substrates are involved in the reaction, it is called multicomponent. This type of chemical reactions is of major interest as it allows for reducing the number of stages and therefore for preserving the environment. The 1.3 dicarbonyl compounds are also of great interest as these synthetic platforms allow for the creation of several covalent reactions in one operation due to the presence of four reactional sites. This article presents the domino and/or multicomponent reactions involving at least one 1.3 dicarbonyl compound.

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AUTHORS

  • Damien BONNE: Senior Lecturer, Aix-Marseille University - Institut des Sciences Moléculaires de Marseille, CNRS-UMR 6263, Centre Saint-Jérôme

  • Thierry CONSTANTIEUX: University Professor, Aix-Marseille University - Institut des Sciences Moléculaires de Marseille, CNRS-UMR 6263, Centre Saint-Jérôme

  • Yoann COQUEREL: CNRS Research Fellow, Aix-Marseille University - Institut des Sciences Moléculaires de Marseille, CNRS-UMR 6263, Centre Saint-Jérôme

  • Jean RODRIGUEZ: University Professor, Aix-Marseille University - Institut des Sciences Moléculaires de Marseille, CNRS-UMR 6263, Centre Saint-Jérôme

 INTRODUCTION

A recently conceptualized strategy , although used for several billion years by Nature to build living molecules, consists in using modern and more efficient synthesis tools (i.e. chemical reactions) to create several covalent bonds in the same operation through a reaction between two (or more) different substrates .

Thus, a domino reaction is a chemical transformation that creates two or more covalent bonds through a reaction cascade in a single operation and without changing the conditions of the reaction .

Furthermore, a transformation that involves at least three different substrates and whose product contains a substantial part of each of the substrates, regardless of the mechanism involved, is referred to as a multicomponent reaction .

It's clear, then, that the use of domino and/or multicomponent reactions in a synthesis reduces the total number of steps, thus meeting the criteria of efficiency and cleanliness now required. Fewer steps mean savings in waste, human resources, raw materials and energy. Similarly, domino and/or multicomponent reactions often eliminate the need for protection/deprotection steps, as well as purification of reaction intermediates. Transformations enabling the creation of several covalent bonds in the same operation have become indispensable tools in green chemistry

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Use of 1,3-dicarbonyl derivatives in domino and multicomponent reactions