研究目的
The combination of photoredox and enzymatic catalysis for the direct asymmetric one-pot synthesis of 2,2-disubstituted indol-3-ones from 2-arylindoles through concurrent oxidization and alkylation reactions.
研究成果
A mild enantioselective concurrent photo-enzymatic protocol to access 2,2-disubstituted indol-3-ones from 2-arylindoles has been developed. This work presents the first example of combining the non-natural catalytic activity of hydrolase with visible light catalysis to achieve an asymmetric synthesis, and no cofactors are required.
研究不足
The reaction requires specific conditions such as the presence of O2, visible light, and the use of specific catalysts (Ru(bpy)3Cl2·6 H2O and WGL). The enzyme's activity decreases over time, affecting the reaction's efficiency.
1:Experimental Design and Method Selection:
The study combines photoredox catalysis with enzymatic catalysis for the synthesis of 2,2-disubstituted indol-3-ones. 2-Arylindoles are photocatalytically oxidized to 2-arylindol-3-one, followed by enantioselective alkylation with ketones catalyzed by wheat germ lipase (WGL).
2:Sample Selection and Data Sources:
2-Phenylindole (1 a) and acetone (2 a) were chosen as the model substrates.
3:List of Experimental Equipment and Materials:
Ru(bpy)3Cl2·6 H2O (bpy = 2,2’-bipyridine) was used as a photoredox catalyst, and WGL was used as the biocatalyst.
4:Experimental Procedures and Operational Workflow:
The model reaction was carried out in MeCN in the presence of O2 (O2 balloon) at room temperature under irradiation of a 23 W compact fluorescent lamp (CFL) for 60 hours.
5:Data Analysis Methods:
The yield and enantioselectivity of the product were determined by HPLC analysis using a chiral-phase column (AD-H).
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