Photoinduced Arylation of Acridinium Salts: Tunable Photoredox Catalysts for C–O Bond Cleavage,Journal of the American Chemical Society

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Photoinduced Arylation of Acridinium Salts: Tunable Photoredox Catalysts for C–O Bond Cleavage
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2022-03-22 , DOI: 10.1021/jacs.1c12961
Yi-Xuan Cao ₁ , Gan Zhu _{1,

2} , Yiqun Li ₂ , Nolwenn Le Breton ₃ , Christophe Gourlaouen ₃ , Sylvie Choua ₃ , Julien Boixel ₁ , Henri-Pierre Jacquot de Rouville ₃ , Jean-François Soulé ₁

Affiliation

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^βO–Ar bond cleavage of diol monoarylethers to afford 1,2-diols in good yields.

中文翻译：

吖啶盐的光诱导芳基化：用于 C-O 键断裂的可调光氧化还原催化剂

N-取代的吖啶盐的光诱导芳基化已经被开发并且表现出高官能团耐受性（例如卤素、腈、酮、酯和硝基）。已经在一步过程中合成了广泛的精心修饰的 C9 芳基化吖啶基催化剂，这些催化剂具有微调的光物理和光化学性质，即激发态寿命和氧化还原电位。这些功能化的吖啶盐后来在 1,2-二醇衍生物的光氧化还原催化碎裂（木质素模型）中进行了评估。其中，2-溴苯基取代的N-甲基吖啶鎓在选择性 C ^β O-Ar 键断裂二醇单芳基醚以良好收率提供 1,2-二醇方面的性能优于所有光氧化还原催化剂，包括商业 Fukuzumi 的催化剂。

更新日期：2022-03-22

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