Energy-Transfer-Enabled 1,4-Amino Migration and C–O Diradical Recombination for Norrish–Yang-Type Epoxidation DOI
Danna Chen,

Lulu Qin,

Dan Luo

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 22, 2025

An energy-transfer-enabled photochemical strategy merges 1,4-nitrogen migration with Norrish-Yang-type epoxidation to achieve skeletal editing of molecular frameworks. This approach bypasses classical di-π-methane rearrangements, providing an oxidant-free and atom-economical route epoxides via controlled C-O diradical recombination. The protocol accommodates >40 diverse substrates, including arenes, heterocycles, bioactive motifs, enabling late-stage functionalization complex architectures. Scalability is demonstrated through gram-scale synthesis (84% yield) one-pot cascades. Mechanistic studies reveal a triplet energy-transfer pathway distinct from radical chain processes, nitrogen directing regioselective

Language: Английский

Energy-Transfer-Enabled 1,4-Amino Migration and C–O Diradical Recombination for Norrish–Yang-Type Epoxidation DOI
Danna Chen,

Lulu Qin,

Dan Luo

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 22, 2025

An energy-transfer-enabled photochemical strategy merges 1,4-nitrogen migration with Norrish-Yang-type epoxidation to achieve skeletal editing of molecular frameworks. This approach bypasses classical di-π-methane rearrangements, providing an oxidant-free and atom-economical route epoxides via controlled C-O diradical recombination. The protocol accommodates >40 diverse substrates, including arenes, heterocycles, bioactive motifs, enabling late-stage functionalization complex architectures. Scalability is demonstrated through gram-scale synthesis (84% yield) one-pot cascades. Mechanistic studies reveal a triplet energy-transfer pathway distinct from radical chain processes, nitrogen directing regioselective

Language: Английский

Citations

0