A Mild, One-Pot Stadler-Ziegler Synthesis of Arylsulfides Facilitated by Photoredox Catalysis in Batch and Continuous-Flow

Visible advance: A mild, one‐pot Stadler–Ziegler process for CS bond formation has been developed. The method employs the photoredox catalyst [Ru(bpy)3Cl2]⋅6 H2O irradiated with visible light. A variety of aryl–alkyl and diaryl sulfides were prepared from readily available arylamines and aryl/alkyl...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2013-07, Vol.52 (30), p.7860-7864
Main Authors: Wang, Xiao, Cuny, Gregory D., Noël, Timothy
Format: Article
Language:English
Subjects:
Amines
Aromatic compounds
Bonding
Catalysis
CS bond formation
Hydrocarbons, Aromatic - chemical synthesis
Light
microflow chemistry
Microreactors
Molecular Structure
one-pot processes
Organic compounds
Photochemical Processes
Ruthenium - chemistry
Sulfides
Sulfides - chemical synthesis
Synthesis
visible-light photoredox catalysis
Water
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Summary:Visible advance: A mild, one‐pot Stadler–Ziegler process for CS bond formation has been developed. The method employs the photoredox catalyst [Ru(bpy)3Cl2]⋅6 H2O irradiated with visible light. A variety of aryl–alkyl and diaryl sulfides were prepared from readily available arylamines and aryl/alkylthiols in good yields. The use of a photo microreactor led to a significant improvement with respect to safety and efficiency.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201303483