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

Authors

  • Dr. Xiao Wang,

    Corresponding author
    1. Harvard NeuroDiscovery Center, Harvard Medical School and Brigham & Women's Hospital, 65 Landsdowne Street, Cambridge, MA 02139 (USA)
    • Harvard NeuroDiscovery Center, Harvard Medical School and Brigham & Women's Hospital, 65 Landsdowne Street, Cambridge, MA 02139 (USA)
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  • Prof. Dr. Gregory D. Cuny,

    Corresponding author
    1. Harvard NeuroDiscovery Center, Harvard Medical School and Brigham & Women's Hospital, 65 Landsdowne Street, Cambridge, MA 02139 (USA)
    2. Department of Pharmacological and Pharmaceutical Sciences, College of Pharmacy, University of Houston, 549 A Science and Research Bldg 2, Houston, TX 77204 (USA)
    • Harvard NeuroDiscovery Center, Harvard Medical School and Brigham & Women's Hospital, 65 Landsdowne Street, Cambridge, MA 02139 (USA)
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  • Dr. Timothy Noël

    Corresponding author
    1. Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven (The Netherlands)
    • Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven (The Netherlands)
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  • 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.

Abstract

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Visible advance: A mild, one-pot Stadler–Ziegler process for C[BOND]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.

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