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

Autor: Cao YX; Univ Rennes, CNRS, UMR 6226, F-3500 Rennes, France., Zhu G; Univ Rennes, CNRS, UMR 6226, F-3500 Rennes, France.; Department of Chemistry, Jinan University, 511443 Guangzhou, China., Li Y; Department of Chemistry, Jinan University, 511443 Guangzhou, China., Le Breton N; Institut de Chimie de Strasbourg, CNRS UMR 7177, Université de Strasbourg, 4 rue Blaise Pascal, 67000 Strasbourg, France., Gourlaouen C; Institut de Chimie de Strasbourg, CNRS UMR 7177, Université de Strasbourg, 4 rue Blaise Pascal, 67000 Strasbourg, France., Choua S; Institut de Chimie de Strasbourg, CNRS UMR 7177, Université de Strasbourg, 4 rue Blaise Pascal, 67000 Strasbourg, France., Boixel J; Univ Rennes, CNRS, UMR 6226, F-3500 Rennes, France., Jacquot de Rouville HP; Institut de Chimie de Strasbourg, CNRS UMR 7177, Université de Strasbourg, 4 rue Blaise Pascal, 67000 Strasbourg, France., Soulé JF; Univ Rennes, CNRS, UMR 6226, F-3500 Rennes, France.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2022 Apr 06; Vol. 144 (13), pp. 5902-5909. Date of Electronic Publication: 2022 Mar 22.
DOI: 10.1021/jacs.1c12961
Abstrakt: 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.
Databáze: MEDLINE