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

Radical approaches for C(sp3)–N bond cleavage in deaminative transformations DOI
J. Kim,

Eun Song Lim,

Ji Yeon Park

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review summarizes recent advancements in radical-mediated deaminative transformations, focusing on the mechanisms, substrate compatibility, and emerging applications synthetic organic chemistry.

Language: Английский

Citations

0
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

Citations

2