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Nitrene Radical Intermediates in Catalytic Synthesis.

Petrus F Kuijpers1, Jarl Ivar van der Vlugt1, Sven Schneider2

  • 1Van 't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam (UvA), Science Park 904, 1098 XH, Amsterdam, The Netherlands.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 5, 2017
PubMed
Summary

Nitrene radical complexes are key intermediates in organic synthesis, enabling C-H functionalization and aziridination. Recent advances include using challenging non-activated aliphatic azides for catalytic reactions.

Keywords:
C−H aminationelectronic structure-reactivity correlationsmetalloradical catalysisnoninnocent ligandsradicals

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Area of Science:

  • Organometallic Chemistry
  • Synthetic Organic Chemistry

Background:

  • Nitrene radical complexes are reactive intermediates with spin density on nitrogen.
  • They are crucial in various organic synthesis reactions like C-H functionalization and aziridination.
  • Their electronic structure is akin to one-electron reduced Fischer type nitrenes.

Purpose of the Study:

  • To describe the electronic structure of nitrene radical complexes.
  • To emphasize their utility in catalytic synthesis of organic products.
  • To highlight recent developments in the field of nitrene radical chemistry.

Main Methods:

  • Intramolecular single electron transfer to the nitrene moiety.
  • Utilizing open-shell cobalt(II) catalysts for nitrene radical generation.
  • Employing redox-active ligands to facilitate electron transfer.

Main Results:

  • Nitrene radicals can be generated via intramolecular single electron transfer.
  • Cobalt(II) complexes are well-characterized for spectroscopic and reactivity studies.
  • Successful use of challenging non-activated aliphatic organic azides as precursors.

Conclusions:

  • Nitrene radical complexes possess unique electronic structures and are valuable synthetic intermediates.
  • Catalysis involving nitrene radicals has advanced significantly with new precursors and metal catalysts.
  • The field continues to evolve, expanding the scope of reactions accessible through nitrene radical chemistry.