光氧化还原催化生成烷氧基自由基实现温和条件下的选择性 C(sp(3))-H 官能化反应。
Generation of Alkoxyl Radicals by Photoredox Catalysis Enables Selective C(sp(3))-H Functionalization under Mild Reaction Conditions.
机构信息
State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai, 201210, China.
出版信息
Angew Chem Int Ed Engl. 2016 Jan 26;55(5):1872-5. doi: 10.1002/anie.201510014. Epub 2015 Dec 17.
Reported herein is the first visible-light-induced formation of alkoxyl radicals from N-alkoxyphthalimides, and the Hantzsch ester as the reductant is crucial for the reaction. The selective hydrogen atom abstraction by the alkoxyl radical enables C(sp(3))-H allylation and alkenylation reactions under mild reaction conditions at room temperature. Broad substrate variations, including a structurally complexed steroid, undergo the C(sp(3))-H functionalization reaction effectively with high regio- and chemoselectivity.
本文首次报道了可见光诱导 N-烷氧基邻苯二甲酰亚胺生成烷氧基自由基，其中 Hantzsch 酯作为还原剂对于反应至关重要。烷氧基自由基的选择性氢原子攫取使得在温和的反应条件下（室温下）能够实现 C(sp(3))-H 烯丙基化和烯基化反应。广泛的底物变化，包括结构复杂的甾体，都能有效地进行 C(sp(3))-H 官能化反应，具有高区域和化学选择性。
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