Facile Cleavage of Activated Ketones: An Access to Thioethers via In SituGeneration of Anhydrides by Pummerer-Type Rearrangement

Autor: Sivaraj, Chandrasekaran, Muthuvel, Karthick, Udayan, Ajay Thonipalliyalil, Premkumar, Egambaram, Gandhi, Thirumanavelan
Zdroj: The Journal of Organic Chemistry; May 2024, Vol. 89 Issue: 10 p7020-7026, 7p
Abstrakt: Herein, we report an oxygen insertion in activated ketones from simple inorganic carbonates for the synthesis of symmetric aromatic anhydrides. For the first time, Li2CO3acts as an oxygen source and the in situgenerated symmetric aromatic anhydrides undergo Pummerer-type rearrangement to access α-benzoyloxy–thioethers. Attractively, this protocol occurs under metal-, ligand-, and oxidant-free conditions and is compatible with a wide range of substrates. Control experiments reveal the reaction pathway.
Databáze: Supplemental Index