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

被引:29
作者
Cao, Yi-Xuan [1 ]
Zhu, Gan [1 ,2 ]
Li, Yiqun [2 ]
Le Breton, Nolwenn [3 ]
Gourlaouen, Christophe [3 ]
Choua, Sylvie [3 ]
Boixel, Julien [1 ]
De Rouville, Henri-Pierre Jacquot [3 ]
Soule, Jean-Francois [1 ]
机构
[1] Univ Rennes, CNRS, UMR 6226, F-3500 Rennes, France
[2] Jinan Univ, Dept Chem, Guangzhou 511443, Peoples R China
[3] Univ Strasbourg, Inst Chim Strasbourg, CNRS, UMR 7177, F-67000 Strasbourg, France
关键词
VISIBLE-LIGHT PHOTOREDOX; PHOTOINDUCED ELECTRON-TRANSFER; PHOTOCATALYTIC OXIDATION; CHARGE-SHIFT; H FUNCTIONALIZATION; LIGNIN; CATALYSIS; COMPLEXES; MODEL; ARYL;
D O I
10.1021/jacs.1c12961
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A photoinduced arylation of N-substituted acridi-nium salts has been developed and has exhibited a high functionalgroup tolerance (e.g., halogen, nitrile, ketone, ester, and nitro). Abroad range of well-decorated C9-arylated acridinium-basedcatalysts withfine-tuned photophysical and photochemical proper-ties, namely, excited-state lifetimes and redox potentials have beensynthetized in a one-step procedure. These functionalizedacridinium salts were later evaluated in the photoredox-catalyzedfragmentation of 1,2-diol derivatives (lignin models). Among them,2-bromophenyl substitutedN-methyl acridinium has outperformedall photoredox catalysts, including commercial Fukuzumi's catalyst,for the selective C beta O-Ar bond cleavage of diol monoarylethers toafford 1,2-diols in good yields.
引用
收藏
页码:5902 / 5909
页数:8
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