Silyl Radical as an Isocyanide Transfer Agent for Giese-Type Reactions Involving Aliphatic Amines.
Org Lett
; 26(24): 5172-5176, 2024 Jun 21.
Article
in En
| MEDLINE
| ID: mdl-38864545
ABSTRACT
Herein we report silyl radicals serve as isocyanide transfer agents for Giese-type reaction from aliphatic amines and electron-deficient olefins. α-Primary, α-secondary, and sterically encumbered α-tertiary primary amines could be easily converted into isocyanides for coupling with electron-deficient olefins by employing latent silyl radicals under visible light irradiation. Notably, the abstraction of silane-mediated isocyanide not only enables voltage-independent activation of strong C-N bonds but also represents a mechanistic alternative Giese-type reaction in which single electron reduction and protonation processes are replaced by direct hydrogen atom transfer. This transformation occurs under photoinduced catalyst-free conditions and exhibits excellent functional group compatibility and mild reaction conditions.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2024
Document type:
Article
Affiliation country: