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Updated: Jun 27, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
A phosphine-mediated conversion of azides into diazo compounds
Eddie L Myers1, Ronald T Raines
1Department of Biochemistry, University of Wisconsin-Madison, 433 Babcock Drive, Madison, WI 53706, USA.
A new mild method converts azides into diazo compounds using an acyl triazene intermediate, inspired by the Staudinger ligation. This approach is suitable for complex molecules with sensitive functional groups in organic synthesis.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Diazo compounds are valuable synthetic intermediates.
- Traditional synthesis methods pose challenges with delicate functional groups.
Purpose of the Study:
- To develop a mild and versatile method for synthesizing diazo compounds.
- To enable diazo compound synthesis in the presence of sensitive functional groups.
Main Methods:
- Utilizing the Staudinger ligation as inspiration.
- Employing an acyl triazene intermediate for diazo compound formation.
- Converting a broad range of azides to diazo compounds.
Main Results:
- Successful synthesis of diazo compounds under mild conditions.
- Demonstrated compatibility with delicate functional groups.
- Broad applicability across various azide substrates.
Conclusions:
- The Staudinger ligation-inspired method offers a mild route to diazo compounds.
- This method expands the synthetic utility of diazo compounds in complex molecule synthesis.
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