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

被引：34

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2022年 / 144卷 / 13期

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

页码：5902 / 5909

页数：8

共 57 条

[1] Covalent modification of carbon surfaces by aryl radicals generated from the electrochemical reduction of diazonium salts [J].