Direct Synthesis of 1,4-Diols from Alkenes by Iron-Catalyzed Aerobic Hydration and C-H Hydroxylation

Direct Synthesis of 1,4-Diols from Alkenes by Iron-Catalyzed Aerobic Hydration and C-H Hydroxylation
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DOI:
10.1002/anie.201308675
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发表时间:
2014-03-03
影响因子:
16.6
通讯作者:
Taniguchi, Tsuyoshi
Taniguchi, Tsuyoshi
中科院分区:
化学1区
文献类型:
--
作者:
Hashimoto, Takuma;Hirose, Daisuke;Taniguchi, Tsuyoshi

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通过铁催化的有氧水合,可以很容易地从烯烃得到各种 1,4-二醇。该反应体系由用户友好的铁酞菁络合物、硼氢化钠和分子氧组成。此外,还检查了模型反应中额外配体对铁络合物的影响。第二个羟基是通过直接C(sp(3))H氧化作用安装的,该氧化作用基于通过烯烃的形式水合形成的瞬时烷氧基的[1,5]氢转移过程。
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.