化学
激进的
铱
邻接
催化作用
组合化学
试剂
光催化
铜
硝基
光化学
氧化还原
表面改性
协调球
分子
有机化学
光催化
烷基
物理化学
作者
Alexander Reichle,Magdalena Koch,Hannes Sterzel,Lea‐Joy Großkopf,Johannes Floß,Julia Rehbein,Oliver Reiser
标识
DOI:10.1002/anie.202219086
摘要
We report the visible light-mediated copper-catalyzed vicinal difunctionalization of olefins utilizing bromonitroalkanes as ATRA reagents. This protocol is characterized by high yields and fast reaction times under environmentally benign reaction conditions with exceptional scope, allowing the rapid functionalization of both activated and unactivated olefins. Moreover, late-stage functionnalization of biologically active molecules and upscaling to gram quantities is demonstrated, which offers manifold possibilities for further transformations, e.g. access to nitro- and aminocyclopropanes. Besides the synthetic utility of the title transformation, this study undergirds the exclusive role of copper in photoredox catalysis showing its ability to stabilize and interact with radical intermediates in its coordination sphere. EPR studies suggest that such interactions can even outperform a highly favorable cyclization of transient to persistent radicals contrasting iridium-based photocatalysts.
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