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Continuous-Flow Synthesis of 1-Substituted Benzotriazoles from Chloronitrobenzenes and Amines in a C[BOND]N Bond Formation/Hydrogenation/Diazotization/Cyclization Sequence

Authors

  • Dr. Mao Chen,

    1. Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA)
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  • Prof. Dr. Stephen L. Buchwald

    Corresponding author
    1. Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA)
    • Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA)
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  • We thank Novartis International AG for funding. We thank Dr. Nathan Jui and Dr. Christine Nguyen for assistance with the preparation of this manuscript. MIT has patents on some of the ligands and precatalysts used in this work from which S.L.B. receives royalty payments.

Abstract

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Zwei Ansätze wurden für die regiospezifische Synthese 1-substituierter Benzotriazole unter kontinuierlichen Fließbedingungen entwickelt. Sie beginnen entweder mit einer SNAr-Reaktion bei hoher Temperatur oder einer Pd-Katalyse und umfassen anschließende Multiphasen-Prozesse, die die effiziente mehrstufige Synthese von Benzotriazolen ermöglichen (siehe Bild).

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