Visible-Light-Promotedα‑C(sp<sup>3</sup>)–H Amidation of Cyclic Ethersunder Redox-Neutral Conditions

Reported herein is a visible-light-promoted strategy for the α-C(sp<sup>3</sup>)–H amidation of cyclic ethers using <i>N</i>-acyloxy­amide as an oxidative amidating reagent. This transformation provides a straightforward approach to various α-amidated cyclic ethers under metal- and additive-free conditions. The synthetic utility of the products was demonstrated through facile transformations, including reduction, allylation, acylation, sulfonamidation, and gram-scale reactions. Preliminary mechanistic studies suggest a radical/radical cross-coupling process, with C(sp<sup>3</sup>)–H bond cleavage identified as the rate-determining step.

Publication Details

Journal
Figshare
Published
2025-03-17
DOI
https://doi.org/10.1021/acs.orglett.5c00337.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Visible-Light-Promotedα‑C(sp3)–H Amidation of Cyclic Ethersunder Redox-Neutral Conditions

Figshare
Radical Photochemical Reactions
article

Visible-Light-Promotedα‑C(sp3)–H Amidation of Cyclic Ethersunder Redox-Neutral Conditions

article en

Abstract

Reported herein is a visible-light-promoted strategy for the α-C(sp<sup>3</sup>)–H amidation of cyclic ethers using <i>N</i>-acyloxy­amide as an oxidative amidating reagent. This transformation provides a straightforward approach to various α-amidated cyclic ethers under metal- and additive-free conditions. The synthetic utility of the products was demonstrated through facile transformations, including reduction, allylation, acylation, sulfonamidation, and gram-scale reactions. Preliminary mechanistic studies suggest a radical/radical cross-coupling process, with C(sp<sup>3</sup>)–H bond cleavage identified as the rate-determining step.

Figshare
Openalex Percentile: Top 63%
Radical Photochemical Reactions
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Visible-Light-Promotedα‑C(sp<sup>3</sup>)–H Amidation of Cyclic Ethersunder Redox-Neutral Conditions · Figshare (2025) | TGRS Research Map | TGRS