Simplifying Nitration Chemistry with Bench-stable Organic Nitrating Reagents

Authors

  • Subrata Patra Department für Chemie, Biochemie und Pharmazie, University of Bern, Bern, CH-3012 Bern
  • Vasiliki Valsamidou Department für Chemie, Biochemie und Pharmazie, University of Bern, Bern, CH-3012 Bern
  • Dmitry Katayev Department für Chemie, Biochemie und Pharmazie, University of Bern, Bern, CH-3012 Bern

DOI:

https://doi.org/10.2533/chimia.2024.32

PMID:

38430061

Keywords:

Nitration, Nitronium ion, Nitryl radicals, Organic nitrating reagent, Photoredox

Abstract

Nitro compounds play a crucial role in academia and industries, serving as building blocks for the synthesis of drugs, agrochemicals, and materials. Nitration, a fundamental process in organic synthesis, has undergone significant evolution since the 19th century. While electrophilic nitration dominates historically, recent decades have seen a focus on new reagents and their reactivity modes for achieving mild and robust synthesis of nitro compounds. Our group has a longstanding interest in developing cost-effective, readily available, recyclable nitrating reagents derived from organic scaffolds. These reagents serve as a controllable source of nitryl radical and nitronium ion species, enabling mild and practical nitration of hydrocarbons with exceptional functional group tolerance. This account details the development of nitrating reagents and their diverse applications in catalytic nitration across various classes of organic molecules.

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Published

2024-02-28

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