Year: 2025
Type: article
Abstract: Two complementary and operationally simple methods enable the efficient perfluoroalkylation of organodiselenides: (i) direct visible‐light irradiation at 395 nm in aqueous MeCN with R F –I, requiring no photocatalyst, and (ii) a base‐promoted protocol using KOH in MeCN under dark conditions. Both furnished perfluoroalkyl selenoethers in excellent yields, while only the photoinduced protocol delivered good to excellent yields of perfluoroalkyl thioethers from organodisulfides. The direct irradiation approach also enables the preparation of Se‐ and S‐perfluoroalkylated derivatives of selenocysteine and cysteine, highlighting the applicability to biologically relevant substrates. Both protocols feature excellent chemical selectivity, good functional group tolerance, mild conditions, and simple operation. Compared with existing photocatalytic and thermal methods, these approaches provide greater versatility and operational simplicity, exemplified by the gram‐scale synthesis of a perfluoroalkyl selenoether in excellent yield.
Language: English
Subfield: Toxicology
Domain: Life Sciences
Open Access status: hybrid
Estimated APC paid: $4,330
Awards: G1958562451, G7378882120, G7425517116
OpenAlex ID: W4415784253