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铁催化烯烃的有氧水合和 C-H 羟化直接合成 1,4-二醇。

Direct synthesis of 1,4-diols from alkenes by iron-catalyzed aerobic hydration and C-H hydroxylation.

机构信息

School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan).

出版信息

Angew Chem Int Ed Engl. 2014 Mar 3;53(10):2730-4. doi: 10.1002/anie.201308675. Epub 2014 Feb 2.

Abstract

Various 1,4-diols are easily accessible from alkenes through iron-catalyzed aerobic hydration. The reaction system consists of a user-friendly iron phthalocyanine complex, sodium borohydride, and molecular oxygen. Furthermore, the effect of additional ligands on the iron complex was examined for a model reaction. The second hydroxy group is installed by direct C(sp(3))-H oxygenation, which is based on a [1,5] hydrogen shift process of a transient alkoxy radical that is formed by formal hydration of the olefin.

摘要

各种 1,4-二醇可通过铁催化的有氧水合作用从烯烃中轻易获得。该反应体系由一种易于使用的铁酞菁配合物、硼氢化钠和分子氧组成。此外,还研究了模型反应中额外配体对铁配合物的影响。第二个羟基是通过直接 C(sp(3))-H 氧化安装的,这是基于瞬态烷氧基自由基的[1,5]氢迁移过程,该自由基是由烯烃的形式水合作用形成的。

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