Reduction and Hydrocyanation of Aziridines with C−C Bond Cleavage

The carbon‐carbon bond in three‐membered ring of 2,3‐diaryl aziridines was reductively cleaved to give the corresponding dibenzylamine derivatives by electrocyclic ring opening of N‐Li or N‐Na aziridines followed by reduction of the 2‐azaallyl anion formed with sodium borohydride in ethanol. Hydrocy...

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Bibliographic Details
Published in:European journal of organic chemistry 2024-10, Vol.27 (39), p.n/a
Main Authors: Kawamoto, Yuki, Yoshimura, Tomoyuki, Matsuo, Jun‐ichi
Format: Article
Language:English
Subjects:
Anions
Azaallyl anions
Aziridines
Carbon
Cyano groups
C−C bond cleavage
Dihydrogenation
Ethanol
Hydrocyanation
Ring opening
Sodium
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Summary:The carbon‐carbon bond in three‐membered ring of 2,3‐diaryl aziridines was reductively cleaved to give the corresponding dibenzylamine derivatives by electrocyclic ring opening of N‐Li or N‐Na aziridines followed by reduction of the 2‐azaallyl anion formed with sodium borohydride in ethanol. Hydrocyanation of the 2‐azaallyl anion with trimethylsilyl cyanide gave a secondary amine bearing a cyano group at the benzylic position. The effects of substituents on the electrocyclic ring opening of N‐Li aziridines were also clarified. Unusual C−C bond cleavage of 2,3‐diaryl aziridines took place to afford secondary amines by formal dihydrogenation and hydrocyanation. Formal dehydrogenation was performed by electrocyclic ring opening of N‐Li or N‐Na aziridines to azaallyl anions followed by reduction with NaBH4. Formal hydrocyanation was realized by treating azaallyl anions with Me3SiCN.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400613