Facile access to nitroarenes and nitroheteroarenes using N-nitrosaccharin

Nat Commun. 2019 Jul 30;10(1):3410. doi: 10.1038/s41467-019-11419-y.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry
  • Catalysis
  • Molecular Structure
  • Nitro Compounds / chemical synthesis
  • Nitro Compounds / chemistry*

Substances

  • Acids
  • Nitro Compounds