Silyl Radical as an Isocyanide Transfer Agent for Giese-Type Reactions Involving Aliphatic Amines DOI

Yuqing Ma,

Muliang Zhang, Shi‐Kai Tian

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5172 - 5176

Published: June 12, 2024

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, sterically encumbered α-tertiary primary could be easily converted into isocyanides coupling with olefins by employing latent under visible light irradiation. Notably, the abstraction of silane-mediated not only enables voltage-independent activation strong C-N bonds but also represents a mechanistic alternative in which single electron reduction protonation processes are replaced direct hydrogen atom transfer. This transformation occurs photoinduced catalyst-free conditions exhibits excellent functional group compatibility mild conditions.

Language: Английский

Silyl Radical as an Isocyanide Transfer Agent for Giese-Type Reactions Involving Aliphatic Amines DOI

Yuqing Ma,

Muliang Zhang, Shi‐Kai Tian

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5172 - 5176

Published: June 12, 2024

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, sterically encumbered α-tertiary primary could be easily converted into isocyanides coupling with olefins by employing latent under visible light irradiation. Notably, the abstraction of silane-mediated not only enables voltage-independent activation strong C-N bonds but also represents a mechanistic alternative in which single electron reduction protonation processes are replaced direct hydrogen atom transfer. This transformation occurs photoinduced catalyst-free conditions exhibits excellent functional group compatibility mild conditions.

Language: Английский

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