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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Iron-Catalyzed Intermolecular C-N Cross-Coupling Reactions via Radical Activation Mechanism.

Subrata Das1, Andreas W Ehlers2, Sima Patra1

  • 1Department of Biological & Synthetic Chemistry, Center of Biomedical Research, SGPGIMS Campus, Raebareli Road, Lucknow, 226014 Uttar Pradesh, India.

Journal of the American Chemical Society
|June 30, 2023
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Summary

A new iron-catalyzed method enables intermolecular C-N cross-coupling amination using tetrazoles and azides with boronic acids. This reaction proceeds via a novel metalloradical mechanism, offering broad synthetic utility in drug discovery.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • Traditional metal-catalyzed C-N cross-coupling reactions are crucial in organic synthesis.
  • Developing novel catalytic systems with unique mechanisms remains a key challenge.

Purpose of the Study:

  • To discover a new intermolecular C-N cross-coupling amination reaction.
  • To explore an iron-catalyzed approach utilizing tetrazoles, azides, and boronic acids.
  • To elucidate the reaction's mechanism and demonstrate its synthetic applicability.

Main Methods:

  • Iron-catalyzed intermolecular C-N cross-coupling amination.
  • Utilized tetrazoles, aromatic and aliphatic azides, and boronic acids as substrates.
  • Investigated a metalloradical activation pathway.

Main Results:

  • Successfully developed a novel iron-catalyzed C-N cross-coupling amination.
  • Demonstrated broad substrate scope with diverse tetrazoles, azides, and boronic acids.
  • Showcased late-stage aminations and a synthesis of a drug candidate.

Conclusions:

  • The discovered iron-catalyzed C-N cross-coupling reaction proceeds via an unprecedented metalloradical mechanism.
  • This method offers significant synthetic utility for medicinal chemistry and drug discovery.
  • The reaction has potential for wide applications in the pharmaceutical industry.