DES‐Type Interactions To Promote Solvent‐Free and Metal‐Free Reactions between Nitrogen‐Containing Heterocycles and Allylic Alcohols

Nitrogen‐containing heterocycles are of great interest to organic chemists since they are present in a wide array of bioactive molecules. The use of allylic alcohols to carry out the allylation of heterocycles has been described as a sustainable alternative for this type of functionalization. Among...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-11, Vol.2022 (44), p.n/a
Main Authors: Martos, Mario, Pérez‐Almarcha, Yanira, Pastor, Isidro M.
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Allyl compounds
Allylation
Benzotriazole
Carbazoles
Catalysis
Chemical reactions
Chemists
DES-type interaction
Materials recovery
Nitrogen
Nitrogen heterocycles
Pyrazole
Reagents
Solvents
Sustainable chemistry
Tetrazoles
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Summary:Nitrogen‐containing heterocycles are of great interest to organic chemists since they are present in a wide array of bioactive molecules. The use of allylic alcohols to carry out the allylation of heterocycles has been described as a sustainable alternative for this type of functionalization. Among the plethora of methodologies described, the use of metals, solvents, or hazardous reagents is ubiquitous. The protocol described in this work has provided a solven‐ and metal‐free alternative, being mediated by the easy‐to‐synthesize and reusable 1,3‐bis(carboxymethyl)imidazolium chloride. The protocol has proved to be compatible with several nitrogen‐containing heterocycles (i. e. indole, pyrazole, triazole, tetrazole, carbazole, indazole, and benzotriazole) and allylic alcohols, providing the allylated‐heterocycles in up to quantitative yield, and it's possible to perform the reaction in preparative scale. Based on various green metrics (atom economy, stoichiometric factor, reaction mass efficiency, materials recovery parameter, E‐factor, and EcoScale), the overall greenness significance of the methodology has been proved. The catalyst [1,3‐bis(carboxymethyl)imidazolium chloride] interacts under neat conditions with the reagents in a DES‐like manner, providing both substrate activation and reaction media, representing a significant improvement on the way to a lower environmental impact.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202201221