Article Dans Une Revue Angewandte Chemie International Edition Année : 2024

In Situ Generation of 1‐Acetylpyrene as a Visible‐Light Photocatalyst for the Thia‐Paternò‐Büchi Reaction

Résumé

The thia‐Paternò‐Büchi reaction represents a straightforward approach to build thietane cores. Unfortunately, the significant instability of thiocarbonyls, particularly thioketones and thioaldehydes, has hitherto rendered this photochemical [2+2]‐cycloaddition underexploited. To address this limitation, we report herein a visible‐light photochemical domino reaction including: the in situ generation of thiocarbonyls though a Norrish type II fragmentation of pyrenacyl sulfides, and the aforementioned thia‐Paternò‐Büchi reaction with various non‐volatile electron‐rich alkenes. The highly efficient synthesis of a wide range of unprecedented thietanes from intrinsically highly unstable thiocarbonyls, such as thioaldehydes and aliphatic thioketones, was made possible by the multitasking capability of pyrenacyl sulfides as a source of thiocarbonyl substrates and as precursors of 1‐acetylpyrene, which acts as the photocatalyst for the thia‐Paternò‐Büchi reaction. The photosensitizer properties of the latter have been experimentally established and a triplet‐triplet Dexter energy transfer based mechanism is proposed.

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hal-04816324 , version 1 (04-12-2025)

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Gabriel Cormier, Clémence Allain, Thomas Boddaert. In Situ Generation of 1‐Acetylpyrene as a Visible‐Light Photocatalyst for the Thia‐Paternò‐Büchi Reaction. Angewandte Chemie International Edition, 2024, 63 (51), pp.e202412602. ⟨10.1002/anie.202412602⟩. ⟨hal-04816324⟩
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