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 inAngewandte Chemie International Edition Vol. 52; no. 30; pp. 7860 - 7864
Main Authors Wang, Xiao, Cuny, Gregory D., Noël, Timothy
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 22.07.2013
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Amines
Aromatic compounds
Bonding
Catalysis
Chemistry
Chemistry, Multidisciplinary
CS bond formation
Hydrocarbons, Aromatic - chemical synthesis
Light
microflow chemistry
Microreactors
Molecular Structure
one-pot processes
Organic compounds
Photochemical Processes
Physical Sciences
Ruthenium - chemistry
Science & Technology
Sulfides
Sulfides - chemical synthesis
Synthesis
visible-light photoredox catalysis
Water
microflow chemistry
SUBSTITUTION
one-pot processes
LIGHT
ARYLATION
C-H FUNCTIONALIZATION
DIARYL SULFIDES
HETEROARENES
CS bond formation
visible-light photoredox catalysis
ELECTRON-TRANSFER
ARYL HALIDES
BOND
EFFICIENT
CS bond formation
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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.
Bibliography:ark:/67375/WNG-SXJ40KM1-H
ArticleID:ANIE201303483
Harvard NeuroDiscovery Center
istex:66EC94A1D104F32167011E10FBC95DE8B2E08EE8
X.W. and G.D.C. thank the Harvard NeuroDiscovery Center for financial support. T.N. would like to acknowledge financial support from the Dutch Science Foundation for a VENI grant. The kind donation of [Ru(bpy)3Cl2]⋅6 H2O by Furuya Metal Co., Ltd. is appreciated by T.N. We are grateful to Prof. Dennis P. Curran for his valuable suggestions.
Dutch Science Foundation
6 H
Cl
2
X.W. and G.D.C. thank the Harvard NeuroDiscovery Center for financial support. T.N. would like to acknowledge financial support from the Dutch Science Foundation for a VENI grant. The kind donation of [Ru(bpy)
3
O by Furuya Metal Co., Ltd. is appreciated by T.N. We are grateful to Prof. Dennis P. Curran for his valuable suggestions.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201303483