Visible-Light-Induced Synthesis of Esters via a Self-Propagating Radical Reaction DOI

Zelin Zhao,

Wenping Li,

Qiujie Shan

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1616 - 1627

Published: Jan. 16, 2025

We herein disclose a visible-light-induced synthesis of O-aryl esters through the cross-dehydrogenative coupling aldehydes with phenols using BrCCl3, in which phenolate functions as both substrate and photosensitizer. This transition-metal- photocatalyst-free esterification is suitable for wide range substrates gives moderate to excellent yields (up 95%). Mechanistic studies provided evidence self-propagating radical reaction involving homolytic cleavage aldehydic C–H bond formation acyl bromides. BrCCl3 serves an oxidant hydrogen atom transfer (HAT) agent.

Language: Английский

Catalyst‐Free Photooxidative N‐Acylation of Azoles with Aldehydes DOI

Nianfeng Gong,

Zelin Zhao,

David James Young

et al.

Chemistry - A European Journal, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

Abstract A catalyst‐free photochemical N‐acylation of azoles with aldehydes has been developed using inexpensive BrCCl 3 as the oxidant. This transition‐metal‐ and photocatalyst‐free amidation proceeded efficiently a wide variety substrates to give corresponding N‐acylazoles, including for late modification pharmaceutically active molecules, on gram‐scale.

Language: Английский

Citations

0

Visible-Light-Induced Synthesis of Esters via a Self-Propagating Radical Reaction DOI

Zelin Zhao,

Wenping Li,

Qiujie Shan

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1616 - 1627

Published: Jan. 16, 2025

We herein disclose a visible-light-induced synthesis of O-aryl esters through the cross-dehydrogenative coupling aldehydes with phenols using BrCCl3, in which phenolate functions as both substrate and photosensitizer. This transition-metal- photocatalyst-free esterification is suitable for wide range substrates gives moderate to excellent yields (up 95%). Mechanistic studies provided evidence self-propagating radical reaction involving homolytic cleavage aldehydic C–H bond formation acyl bromides. BrCCl3 serves an oxidant hydrogen atom transfer (HAT) agent.

Language: Английский

Citations

0