Catalytic Azido‐Hydrazination of Alkenes Enabled by Visible Light: Mechanistic Studies and Synthetic Applications

作者：Peng Wang, Yun-Xuan Luo, Songsong Zhu, Dengfu Lu, Yuefa Gong · 发表于：Advanced Synthesis & Catalysis · 年份：2019 · DOI：10.1002/adsc.201901041 · 被引用次数：29 · 研究领域：Click Chemistry and Applications、Synthesis and Catalytic Reactions、Catalytic C–H Functionalization Methods

Abstract A visible‐light‐enabled catalytic intermolecular azido‐hydrazination method for unactivated alkenes is developed via an orderly radical addition sequence. This transformation features metal‐free and redox‐neutral conditions and is applicable to a wide range of alkenes with commercially available reagents. Mechanistic and kinetic studies reveal that the efficient generation of azide radical enabled by fluorenone under visible‐light is critical to this methodology. The β ‐azido alkyl hydrazines prepared with this reaction can be conveniently derived to valuable synthetic building blocks, and one of the products has been successfully applied in the total synthesis of (±)‐ibrutinib, which is used to treat B cell cancers. magnified image