Palladium-Catalyzed Unimolecular Fragment Coupling of N-Allylamides Bearing a Tethered Nucleophile with the Translocation of an Amide Group

Ryoma Shimazumi; Takuya Kodama; Mamoru Tobisu

doi:10.1055/a-2022-1905

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(01): 134-142
DOI: 10.1055/a-2022-1905

special topic

Advances in Skeletal Editing and Rearrangement Reactions

Palladium-Catalyzed Unimolecular Fragment Coupling of N-Allylamides Bearing a Tethered Nucleophile with the Translocation of an Amide Group

Ryoma Shimazumi

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan

,

Takuya Kodama

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan

^bInnovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan

,

Mamoru Tobisu ∗

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan

^bInnovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan

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Abstract

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Abstract

The palladium-catalyzed reaction of N-allylamides bearing a tethered nucleophile results in the extrusion of an amide moiety in the form of an isocyanate, with its subsequent capture by the pendant nucleophile. This reaction involves the net catalytic transposition of an amide group.

Key words

palladium catalyst - C–N bond activation - amides - isocyanates - elimination - rearrangement

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Referenzen

References

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