Azide‐to‐Diazo Transformation Facilitated by Michael Addition via Phosphazide Formation

ABSTRACT A new type of Michael addition of thiols and amines to 2‐azidoacrylic acid esters through azide‐to‐diazo conversion is disclosed. This unusual transformation proceeds via 1,4‐addition accompanied by N─N bond cleavage of phosphazide intermediates generated in situ from 2‐azidoacrylic acid esters and (4‐dimethylaminophenyl)di( tert ‐butyl)phosphine (Amphos) under practical conditions. The high versatility of the resulting Michael adducts enables the synthesis of a wide variety of organonitrogen compounds.

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Publication Details

Journal
Angewandte Chemie
Published
2026-04-20
DOI
https://doi.org/10.1002/ange.4448961
Primary Topic
Click Chemistry and Applications
Type
article
Field-Weighted Citation Impact
0.00

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article

Azide‐to‐Diazo Transformation Facilitated by Michael Addition via Phosphazide Formation

Tomoki Mano, Gaku Orimoto, Suguru Yoshida, Takahiro Yasuda
Angewandte Chemie
Click Chemistry and Applications
article

Azide‐to‐Diazo Transformation Facilitated by Michael Addition via Phosphazide Formation

Tomoki Mano, Gaku Orimoto, Suguru Yoshida, Takahiro Yasuda
article en

Abstract

ABSTRACT A new type of Michael addition of thiols and amines to 2‐azidoacrylic acid esters through azide‐to‐diazo conversion is disclosed. This unusual transformation proceeds via 1,4‐addition accompanied by N─N bond cleavage of phosphazide intermediates generated in situ from 2‐azidoacrylic acid esters and (4‐dimethylaminophenyl)di( tert ‐butyl)phosphine (Amphos) under practical conditions. The high versatility of the resulting Michael adducts enables the synthesis of a wide variety of organonitrogen compounds.

Angewandte Chemie
Tokyo University of Science (JP)
Japan Society for the Promotion of Science
Openalex Percentile: Top 18%
Click Chemistry and Applications
DOISourceOpenAlex
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Azide‐to‐Diazo Transformation Facilitated by Michael Addition via Phosphazide Formation — Tomoki Mano, Gaku Orimoto, et al. · Angewandte Chemie (2026) | TGRS Research Map | TGRS