可见光诱导的1,6-氢原子转移实现醇的烷基化反应
-Alkylation of Alcohols Enabled by Visible-Light Induced 1,6-Hydrogen Atom Transfer.
作者信息
Shu Wei, Zhang Hui, Huang Yan
机构信息
Department of Chemistry and Shenzhen Grubbs Institute , Southern University of Science and Technology , 518055 , Shenzhen , Guangdong , China.
State Key Laboratory of Elemento-Organic Chemistry , Nankai University , 300071 , Tianjin , China.
出版信息
Org Lett. 2019 Aug 2;21(15):6107-6111. doi: 10.1021/acs.orglett.9b02255. Epub 2019 Jul 24.
Site-selective remote alkylation of alcohol is attractive but challenging in organic synthesis. Herein, we report a novel visible-light mediated -alkylation of alcohol derivatives via the formation of C-C bond through C-H bond functionalization under mild conditions. The use of sulfamate esters enables the directed, otherwise rare 1,6-HAT to generate -selective C-centered radical, which is complementary to δ-selective 1,5-HAT of alcohols. This redox-neutral protocol provides a general and operationally simple method to access -alkylated alcohols.
醇的位点选择性远程烷基化在有机合成中很有吸引力，但具有挑战性。在此，我们报道了一种新型的可见光介导的醇衍生物的β-烷基化反应，该反应通过在温和条件下通过C-H键官能化形成C-C键来实现。氨基磺酸酯的使用能够实现定向的、否则罕见的1,6-氢原子转移（1,6-HAT）以生成β-选择性的碳中心自由基，这与醇的δ-选择性1,5-HAT是互补的。这种氧化还原中性的方法提供了一种通用且操作简单的方法来制备β-烷基化醇。
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