Azide‐to‐Diazo Transformation Facilitated by Michael Addition via Phosphazide Formation
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.
Article Details
Authors (4)
Tomoki Mano
Department of Biological Science and Technology Faculty of Advanced Engineering Tokyo University of Science Tokyo Japan
Takahiro Yasuda
Gaku Orimoto
Department of Biological Science and Technology Faculty of Advanced Engineering Tokyo University of Science Tokyo Japan
Suguru Yoshida
Department of Energy and Hydrocarbon Chemistry