Fe-Catalyzed three-component carboazidation of alkenes with alkanes and trimethylsilyl azide
Wei-Yu Li1, Chuan-Shuo Wu, Zhou Wang
1Key Laboratory for Green Organic Synthesis and Application of Hunan Province, College of Chemistry, Xiangtan University, Hunan, 411105, P. R. China. yangluo@xtu.edu.cn.
Abstract:
Reported herein is a novel iron-catalyzed, DTBP-mediated carboazidation of alkenes using cycloalkanes, CH2Cl2, CHCl3 and CCl4 as alkylating reagents to generate electrophilic or nucleophilic alkyl radicals. Mechanistic studies suggested that the reaction proceeded via the addition of alkyl radicals to alkenes followed by an iron-mediated ligand transfer process. The reaction is unique as it is applicable not only to diversely functionalized electron rich alkenes, but also to electron-poor olefins to provide chain extended azides and γ-azido chloroalkanes in good to high yields.
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