Facile access to nitroarenes and nitroheteroarenes using N-nitrosaccharin

Roxan Calvo, Kun Zhang, Alessandro Passera and Dmitry Katayev ()
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Roxan Calvo: ETH Zürich
Kun Zhang: ETH Zürich
Alessandro Passera: ETH Zürich
Dmitry Katayev: ETH Zürich

Nature Communications, 2019, vol. 10, issue 1, 1-8

Abstract: 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.

Date: 2019
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DOI: 10.1038/s41467-019-11419-y

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