Sodium Hypophosphite as a Halogen Atom Transfer (XAT) Agent under Photocatalytic Conditions

The ability of sodium hypophosphite to generate the phosphorus-centered radical, which can activate the carbon-halogen bond via the halogen atom transfer (XAT) is described. The hydroalkylation of nonactivated alkenes with methyl bromoacetate was performed using sodium hypophosphite as reducing agent under photocatalytic conditions. The key phosphorus centered radical is formed from the hypophosphite anion by hydrogen atom abstraction.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-08-09
DOI
https://doi.org/10.1021/acs.joc.4c01412
Citations
7
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.75

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article

Sodium Hypophosphite as a Halogen Atom Transfer (XAT) Agent under Photocatalytic Conditions

Vladislav S. Kostromitin, Vitalij V. Levin, Alexander D. Dilman, Demian Y. Cheboksarov et al.
7 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
1.75
article

Sodium Hypophosphite as a Halogen Atom Transfer (XAT) Agent under Photocatalytic Conditions

Vladislav S. Kostromitin, Vitalij V. Levin, Alexander D. Dilman, Demian Y. Cheboksarov, Ekaterina V. Malakhova
article en
7 citations

Abstract

The ability of sodium hypophosphite to generate the phosphorus-centered radical, which can activate the carbon-halogen bond via the halogen atom transfer (XAT) is described. The hydroalkylation of nonactivated alkenes with methyl bromoacetate was performed using sodium hypophosphite as reducing agent under photocatalytic conditions. The key phosphorus centered radical is formed from the hypophosphite anion by hydrogen atom abstraction.

The Journal of Organic ChemistryVol. 89(17)
D. Mendeleyev University of Chemical Technology of Russia (RU), Lomonosov Moscow State University (RU), N.D. Zelinsky Institute of Organic Chemistry (RU)
Ministry of Science and Higher Education of the Russian Federation
Openalex Percentile: Top 17%
Radical Photochemical Reactions
1.75
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