Yi Xiangli, Hu Xile
Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne (EPFL) Lausanne 1015 Switzerland
Chem Sci. 2020 Dec 8;12(5):1901-1906. doi: 10.1039/d0sc05952h.
Oxidative amination of alkenes amidyl radical addition is potentially an efficient method to generate allylic amines, which are versatile synthetic intermediates to bioactive compounds and organic materials. Here by combining photochemical generation of amidyl radicals with Cu-mediated β-H elimination of alkyl radicals, we have developed an intermolecular oxidative amination of unactivated alkenes. The reaction relies on tandem photoredox and copper catalysis, and works for both terminal and internal alkenes. The radical nature of the reaction and the mild conditions lead to high functional group tolerance.
烯烃的氧化胺化反应——酰胺基自由基加成潜在地是一种生成烯丙基胺的有效方法,烯丙基胺是合成生物活性化合物和有机材料的通用中间体。在此,通过将酰胺基自由基的光化学产生与铜介导的烷基自由基的β-H消除相结合,我们开发了一种未活化烯烃的分子间氧化胺化反应。该反应依赖于光氧化还原和铜催化的串联过程,对末端烯烃和内烯烃均有效。该反应的自由基性质和温和的条件导致了高官能团耐受性。