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Facile access to nitroarenes and nitroheteroarenes using N-nitrosaccharin.

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.

SUBMITTER: Calvo R

PROVIDER: S-EPMC6667458 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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Facile access to nitroarenes and nitroheteroarenes using N-nitrosaccharin.

Calvo Roxan R Zhang Kun K Passera Alessandro A Katayev Dmitry D

Nature communications 20190730 1

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 pr ...[more]

PMID: 31363083

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