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Article Dans Une Revue Journal of the American Chemical Society Année : 2022

Photoinduced Arylation of Acridinium Salts: Tunable Photoredox Catalysts for C-O Bond Cleavage

Résumé

A photoinduced arylation of N-substituted acridinium salts has been developed and has exhibited a high functional group tolerance (e.g., halogen, nitrile, ketone, ester, and nitro). A broad range of well-decorated C9-arylated acridinium-based catalysts with fine-tuned photophysical and photochemical properties, namely, excited-state lifetimes and redox potentials have been synthetized in a one-step procedure. These functionalized acridinium salts were later evaluated in the photoredox-catalyzed fragmentation of 1,2-diol derivatives (lignin models). Among them, 2-bromophenyl substituted N-methyl acridinium has outperformed all photoredox catalysts, including commercial Fukuzumi’s catalyst, for the selective C(β)O-Ar bond cleavage of diol monoarylethers to afford 1,2-diols in good yields.

Domaines

Chimie
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Dates et versions

hal-03632077 , version 1 (27-04-2022)

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Citer

Yi-Xuan Cao, Gan Zhu, Yiqun Li, Nolwenn Le Breton, Christophe Gourlaouen, et al.. Photoinduced Arylation of Acridinium Salts: Tunable Photoredox Catalysts for C-O Bond Cleavage. Journal of the American Chemical Society, 2022, 144 (13), pp.5902-5909. ⟨10.1021/jacs.1c12961⟩. ⟨hal-03632077⟩
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