2026/01/30 by Tatsuhiro Kawaguchi, Yurina Shioda, Yutaro Hanai +2 · 1 voice
Chemistry · #Radical Photochemical Reactions #Synthesis and Catalytic Reactions #Catalytic C–H Functionalization Methods
paper · doi:10.1021/jacs.5c20284
openalex publication_date 2026/01/30 · openalex created_date 2026/02/01 · openalex updated_date 2026/06/15
-sulfonyl vinylaziridines to the corresponding aminocyclopentanes with adjacent vinyl appendages under visible-light irradiation. Based on the initial findings on the ability of thiazole-2-thione radical cations to act as robust catalysts, pertinent structural modifications of the thiazole-2-thione enabled its excited-state triplet biradical, formed via energy transfer from an iridium-based photocatalyst, to exert high catalytic activity. This system offers a reliable tool for straightforward access to various aminocyclopentanes, which are important components of a range of bioactive molecules and pharmaceuticals. A series of experimental and computational mechanistic investigations underpinned a predominant pathway that involves the triplet biradical as a catalytically active species viable to engage in the covalent activation of vinylaziridine for the ensuing radical cascades. This study sheds light on the potential of excited-state triplet biradicals as radical covalent catalysts, providing a strategy for expanding this promising field of research.