Syntheses of [<sup>17</sup>O]Aryl Sulfoxides, Selenoxides, Phosphine Oxides, and Arsine Oxide by Photo-oxidation Using [<sup>17</sup>O<sub>2</sub>]Dioxygen Generated <i>Ex Situ</i>
Using rose Bengal as photocatalyst and green light for irradiation, aryl sulfides, biaryl selenides, triaryl phosphines, and triphenylarsine were selectively mono-oxidized in hexafluoropropanol by near-stoichiometric amounts of O<sub>2</sub> generated <i>ex situ</i>. Starting from the <sup>17</sup>O-labeled endoperoxide as <sup>17</sup>O<sub>2</sub> precursor, the desired [<sup>17</sup>O]sulfoxides, [<sup>17</sup>O]selenoxides, [<sup>17</sup>O]phosphine oxides, and [<sup>17</sup>O]arsine oxide were obtained with excellent yields (from 70% to 100%), and moderate to very high isotopic enrichments (from 10% to 83% of <sup>17</sup>O). Interestingly, mass and <sup>17</sup>O NMR analyses gave useful information on the moderate stability of the Se═O* and As═O* bonds due to the exchange of O with unlabeled water. In this context, this new synthetic method provides easy and cost-efficient access to a wide variety of <sup>17</sup>O-labeled heteroatom oxides, which are compounds of great interest for various mechanistic investigations.
Authors
- Éric Fouquet (ORCID: https://orcid.org/0000-0002-2081-8155)
- Philippe Hermange (ORCID: https://orcid.org/0000-0002-6156-0648)
- Alexandra Doussot
Institutions
- Centre National de la Recherche Scientifique (FR)
- Université de Bordeaux (FR)
- Institut des Sciences Moléculaires (FR)
- Institut Polytechnique de Bordeaux (FR)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-30
- DOI
- https://doi.org/10.1021/acs.orglett.5c01979
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Agence Nationale de la Recherche
- Ministère de l'Education Nationale, de l'Enseignement Superieur et de la Recherche