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Facile access to nitroarenes and nitroheteroarenes using N-nitrosaccharin

Author

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  • Roxan Calvo

    (ETH Zürich)

  • Kun Zhang

    (ETH Zürich)

  • Alessandro Passera

    (ETH Zürich)

  • Dmitry Katayev

    (ETH Zürich)

Abstract

Nitroaromatics and nitroheteroaromatics serve as key building blocks and intermediates in synthesis, and form the core scaffold of a vast number of materials, dyes, explosives, agrochemicals and pharmaceuticals. However, their synthesis relies on harsh methodologies involving excess mineral acids, which present a number of critical drawbacks in terms of functional group compatibility and environmental impact. Modern, alternative strategies still suffer from significant limitations in terms of practicality, and a general protocol amenable to the direct C-H functionalization of a broad range of aromatics has remained elusive. Herein we introduce a bench-stable, inexpensive, easy to synthesize and recyclable nitrating reagent based on saccharin. This reagent acts as a controllable source of the nitronium ion, allowing mild and practical nitration of both arenes and heteroarenes displaying an exceptional functional group tolerance.

Suggested Citation

  • Roxan Calvo & Kun Zhang & Alessandro Passera & Dmitry Katayev, 2019. "Facile access to nitroarenes and nitroheteroarenes using N-nitrosaccharin," Nature Communications, Nature, vol. 10(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-11419-y
    DOI: 10.1038/s41467-019-11419-y
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