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次磷酸钠在光催化条件下作为卤原子转移(XAT)试剂

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

作者信息

Malakhova Ekaterina V, Kostromitin Vladislav S, Cheboksarov Demian Y, Levin Vitalij V, Dilman Alexander D

机构信息

N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation.

Higher Chemical College, D. Mendeleev University of Chemical Technology of Russia, 125047 Moscow, Miusskaya sq. 9, Russian Federation.

出版信息

J Org Chem. 2024 Sep 6;89(17):12812-12821. doi: 10.1021/acs.joc.4c01412. Epub 2024 Aug 9.

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.

摘要

描述了次磷酸钠生成以磷为中心的自由基的能力,该自由基可通过卤原子转移(XAT)激活碳-卤键。在光催化条件下,以次磷酸钠作为还原剂,实现了溴乙酸甲酯与未活化烯烃的氢烷基化反应。关键的以磷为中心的自由基是由次磷酸根阴离子通过氢原子夺取形成的。

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