光氧化还原介导的游离醇的远程C(sp)-H杂芳基化反应。
Photoredox-mediated remote C(sp)-H heteroarylation of free alcohols.
作者信息
Li Guo-Xing, Hu Xiafei, He Gang, Chen Gong
机构信息
State Key Laboratory and Institute of Elemento-Organic Chemistry , College of Chemistry , Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Nankai University , Tianjin 300071 , China . Email:
Department of Chemistry , The Pennsylvania State University , 104 Chemistry Building, University Park , PA 16802 , USA . Email:
出版信息
Chem Sci. 2018 Oct 30;10(3):688-693. doi: 10.1039/c8sc04134b. eCollection 2019 Jan 21.
We report an efficient and economical method for remote δ C(sp)-H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis. The reaction sequence involves alcoholysis of PFBI-OH with alcohol, generation of an alkoxy radical intermediate by SET reduction, 1,5-HAT, and Minisci-type C-C bond formation. This method uses a slight excess of alcohols, can facilitate reaction at δ methyl and methylene positions, and has been successfully applied to modification of complex drug molecules.
我们报道了一种高效且经济的方法，即在光氧化还原催化下，使用高价碘PFBI-OH氧化剂对游离脂肪醇进行远程δ C(sp)-H杂芳基化反应。反应过程包括PFBI-OH与醇的醇解反应、通过单电子转移还原生成烷氧基自由基中间体、1,5-氢原子转移以及Minisci型碳-碳键形成。该方法使用略微过量的醇，能够促进δ位甲基和亚甲基位置的反应，并且已成功应用于复杂药物分子的修饰。
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