Organocatalytic CS2 insertion into epoxides in neat conditions: a straightforward approach for the efficient synthesis of Di- and tri-thiocarbonates

Marcos López-Aguilar; Nicolás Ríos-Lombardía; Miguel Gallegos; Daniel Barrena-Espés; Joaquín García-Álvarez; Carmen Concellón; Vicente del Amo

doi:10.1039/D4CC05154H

Organocatalytic CS₂ insertion into epoxides in neat conditions: a straightforward approach for the efficient synthesis of Di- and tri-thiocarbonates†

Marcos López-Aguilar,

^a Nicolás Ríos-Lombardía,

^a Miguel Gallegos,

^b Daniel Barrena-Espés,

^b Joaquín García-Álvarez,

*^a Carmen Concellón

*^a and Vicente del Amo

*^a

Author affiliations

* Corresponding authors

^a Laboratorio de Química Sintética Sostenible (QuimSinSos), Departamento de Química Orgánica e Inorgánica, (IUQOEM) and ORFEO-CINQA, Facultad de Química, Universidad de Oviedo, E33071 Oviedo, Spain
E-mail: garciajoaquin@uniovi.es

^b Departamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo, E33071 Oviedo, Spain

Abstract

The straightforward organocatalytic insertion of carbon disulfide (CS₂) into epoxides using either choline chloride (ChCl) or tetrabutylammonium chloride (TBACl) is reported, for the first time, under solvent-free (neat) conditions. Fine-tuning of our system allowed us to obtain either dithiocarbonates (DTCs) or trithiocarbonates (TTCs) with high efficiency. Additionally, a mechanistic proposal is presented, supported by experimental evidence, DFT calculations and wavefunction analyses.

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DOI: https://doi.org/10.1039/D4CC05154H
Article type: Communication
Submitted: 30 sep 2024
Accepted: 19 dec 2024
First published: 23 dec 2024
This article is Open Access

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Chem. Commun., 2025, Advance Article

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Organocatalytic CS₂ insertion into epoxides in neat conditions: a straightforward approach for the efficient synthesis of Di- and tri-thiocarbonates

M. López-Aguilar, N. Ríos-Lombardía, M. Gallegos, D. Barrena-Espés, J. García-Álvarez, C. Concellón and V. del Amo, Chem. Commun., 2025, Advance Article , DOI: 10.1039/D4CC05154H

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Chemical Communications