Photoredox-catalyzed allylation of C(sp <sup>3</sup> )–H bonds in <i>N</i> -trifluoroethyl hydroxylamines or hydroxamides <i>via</i> hydrogen atom transfer

Herein, we present an organophotoredox-catalyzed nitrogen-centered radical-triggered allylation reaction that enables the synthesis of trisubstituted alkenes from MBH adducts and <i>N</i>-trifluoroethylhydroxylamine reagents or hydroxamides <i>via</i> a hydrogen atom transfer (HAT) strategy. When <i>N</i>-trifluoroethylhydroxylamine reagents were employed as radical precursors, various homoallylic α-trifluoromethylamines were generated through 1,2-HAT of the <i>in situ</i>-generated <i>N</i>-trifluoroethyl radicals. Moreover, a series of hydroxamides (1,5-HAT reagents) could be tolerated by this catalytic system, affording the corresponding alkyl amides with excellent yields.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob01288k
Citations
1
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.94
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article

Photoredox-catalyzed allylation of C(sp 3 )–H bonds in N -trifluoroethyl hydroxylamines or hydroxamides via hydrogen atom transfer

Ming-Xian Zhang, Shenghu Yan, Haojie Sha, Tao Wang et al.
1 citations
Organic & Biomolecular Chemistry
Radical Photochemical Reactions
0.94
article

Photoredox-catalyzed allylation of C(sp 3 )–H bonds in N -trifluoroethyl hydroxylamines or hydroxamides via hydrogen atom transfer

Ming-Xian Zhang, Shenghu Yan, Haojie Sha, Tao Wang, Jia‐Yin Wang, Jin‐Long Dai
article en
1 citations

Abstract

Herein, we present an organophotoredox-catalyzed nitrogen-centered radical-triggered allylation reaction that enables the synthesis of trisubstituted alkenes from MBH adducts and <i>N</i>-trifluoroethylhydroxylamine reagents or hydroxamides <i>via</i> a hydrogen atom transfer (HAT) strategy. When <i>N</i>-trifluoroethylhydroxylamine reagents were employed as radical precursors, various homoallylic α-trifluoromethylamines were generated through 1,2-HAT of the <i>in situ</i>-generated <i>N</i>-trifluoroethyl radicals. Moreover, a series of hydroxamides (1,5-HAT reagents) could be tolerated by this catalytic system, affording the corresponding alkyl amides with excellent yields.

Organic & Biomolecular ChemistryVol. 23(44)
Changzhou University (CN), Taizhou University (CN)
Openalex Percentile: Top 21%
Radical Photochemical Reactions
0.94
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Photoredox-catalyzed allylation of C(sp <sup>3</sup> )–H bonds in <i>N</i> -trifluoroethyl hydroxylamines or hydroxamides <i>via</i> hydrogen atom transfer — Ming-Xian Zhang, Shenghu Yan, et al. · Organic & Biomolecular Chemistry (2025) | TGRS Research Map | TGRS