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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Azide-to-Diazo Transformation Facilitated by Michael Addition via Phosphazide Formation
Tomoki Mano1, Takahiro Yasuda1, Gaku Orimoto1
1Department of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science, Tokyo, Japan.
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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