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Issue 1, 2020
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Natural deep eutectic solvents as an efficient and reusable active system for the Nazarov cyclization

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Abstract

Natural deep eutectic solvents have emerged as alternative non-toxic, non-aqueous solvents for an increasing number of synthetic transformations. Remarkably, in some cases one (or more) components of the NaDES plays an active role in the reaction mechanism and directly participates as either a catalyst or a reagent in the reaction. In this paper, we tested several NaDESs in which one of the components is a carboxylic acid as a medium to perform the Nazarov cyclization of divinyl ketones to obtain cyclopentenones, a widespread motif in natural compounds. The reaction conditions were optimized and the scope was investigated on C-, O- and N-derived compounds. To assess the full sustainability of the proposed approach, the recyclability and scalability of the process were investigated, thus proving that multi-gram preparations are possible with complete recycling of the medium.

Graphical abstract: Natural deep eutectic solvents as an efficient and reusable active system for the Nazarov cyclization

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Supplementary files

Article information


Submitted
07 Oct 2019
Accepted
19 Nov 2019
First published
19 Nov 2019

Green Chem., 2020,22, 110-117
Article type
Paper

Natural deep eutectic solvents as an efficient and reusable active system for the Nazarov cyclization

S. Nejrotti, M. Iannicelli, S. S. Jamil, D. Arnodo, M. Blangetti and C. Prandi, Green Chem., 2020, 22, 110
DOI: 10.1039/C9GC03465J

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