Unexpected Reactivity of Nitrones: Catalytic Insertion of CS<sub>2</sub>
A new reactivity mode for nitrones is reported, consisting of the chloride-catalyzed insertion of CS<sub>2</sub> to afford thioamides. This reaction proceeds under metal-free and mild conditions, tolerates a broad family of substrates, and is robust and easily scalable, being successfully applied to the synthesis of the HIV-1 reverse transcriptase inhibitor UC-781. Mechanistic studies, supported by DFT calculations, have revealed the role of chloride anions in the activation of CS<sub>2</sub> and its subsequent insertion into nitrones.
Authors
- Marcos López‐Aguilar (ORCID: https://orcid.org/0000-0001-6960-4118)
- Vicente del Amo (ORCID: https://orcid.org/0000-0003-4237-2817)
- Miguel Gallegos (ORCID: https://orcid.org/0000-0001-7472-8158)
- Carmen Concellón (ORCID: https://orcid.org/0000-0002-2029-1664)
- Nicolás Ríos‐Lombardía (ORCID: https://orcid.org/0000-0003-3501-1407)
- Daniel Barrena-Espés (ORCID: https://orcid.org/0000-0001-6326-9611)
- Joaquín García‐Álvarez (ORCID: https://orcid.org/0000-0003-2266-744X)
Institutions
- Universidad de Oviedo (ES)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-07-24
- DOI
- https://doi.org/10.1021/acs.orglett.5c02611
- Citations
- 1
- Primary Topic
- Synthesis and Reactivity of Sulfur-Containing Compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Gobierno del Principado de Asturias
- Fundación para el Fomento en Asturias de la Investigación Científica Aplicada y la Tecnología
- Agencia Estatal de Investigación