NHC·CS <sub>2</sub> (NHC = <i>N</i> -Heterocyclic Carbene) Species as Reductive Mediators in the Electrosynthesis of Coumarins
Coumarins represent an important class of heterocycles because of their prevalence in nature and their common presence as pharmaceutical structural motifs. However, their synthesis employs harsh conditions or requires a transition metal catalyst, limiting their scalability and sustainability. Herein we report an electrocatalytic synthetic method leading to coumarins using NHC·CS<sub>2</sub> (NHC = N-heterocyclic carbene) species as organic mediators. Using this procedure, a variety of substituted coumarins were obtained in good yields, establishing this electrocatalytic strategy as an attractive synthetic alternative. Based on our observations, a reaction mechanism operating through a one-electron reduction and involving a radical intermediate is proposed.
Authors
- Francis Bru
- Laurens Bourda (ORCID: https://orcid.org/0000-0003-4221-3154)
- Ishfaq Ibni Hashim (ORCID: https://orcid.org/0000-0002-9781-9949)
- K. Van Hecke
- Catherine S. J. Cazin
- Laurence Grimaud
- Maxime R. Vitale
Institutions
- École Nationale Supérieure de Chimie de Montpellier (FR)
- Centre National de la Recherche Scientifique (FR)
- Université Paris Sciences et Lettres (FR)
- Ghent University (BE)
- Sorbonne Université (FR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-03-04
- DOI
- https://doi.org/10.1021/acs.joc.5c03054
- Primary Topic
- N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00