Au(I)-Catalyzed Regioselective Hydrogen Isotope Labeling of Indoles
The gold(I)-catalyzed hydrogen isotope exchange reaction on indoles and related heterocycles is described under mild conditions and low catalyst loadings, using CD<sub>3</sub>OD and D<sub>2</sub>O as readily available deuterium sources. C3-unsubstituted indoles are labeled at the C3 position with exquisite regioselectivity, while C3-substituted indoles are labeled at the C2 position. The method is also applicable to the regioselective tritiation of indoles. Mechanistic studies revealed the involvement of aurated indoles as key intermediates.
Authors
- Sébastien Garcia‐Argote
- Grégory Pieters (ORCID: https://orcid.org/0000-0002-3924-8287)
- Xavier Guinchard (ORCID: https://orcid.org/0000-0003-2353-8236)
- Nicolas Glinsky‐Olivier
- Pierre Milcendeau
- P Colonna
- Mohammed Ramdani (ORCID: https://orcid.org/0000-0003-3177-3367)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Institut de Chimie des Substances Naturelles (FR)
- Commissariat à l'Énergie Atomique et aux Énergies Alternatives (FR)
- Université Paris-Saclay (FR)
- Institut National de Recherche pour l'Agriculture, l'Alimentation et l'Environnement (FR)
- Technologies pour la Santé (FR)
- CEA Paris-Saclay (FR)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-05
- DOI
- https://doi.org/10.1021/acs.orglett.4c03597
- Citations
- 3
- Primary Topic
- Chemical Reactions and Isotopes
- Type
- article
- Field-Weighted Citation Impact
- 0.62
Funders
- Ecoles doctorales, Université Paris-Saclay