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DOI: 10.1055/a-2352-4835
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Iron-Catalyzed Three-Component Asymmetric Carboazidation of Alkenes with Alkanes and Trimethylsilyl Azide

Liang Ge
a   Institute of Chemical Biology, Shenzhen Bay Laboratory, Shenzhen 518132, P. R. of China
,
Yangbin Liu∗
a   Institute of Chemical Biology, Shenzhen Bay Laboratory, Shenzhen 518132, P. R. of China
,
Xiaoming Feng∗
a   Institute of Chemical Biology, Shenzhen Bay Laboratory, Shenzhen 518132, P. R. of China
b   Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (22001177 and 22188101), Shenzhen Bay Laboratory (S201100003 and S211101001-1), Shenzhen Bay Qihang Fellow Program (QH23001), Guangdong Pearl River Talent Program (2021QN020268).
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Abstract

The fusion of transition-metal catalysis with radical chemistry provides a versatile platform for the asymmetric radical carboazidation of alkenes to enable the rapid assembly of highly functionalized chiral azide compounds. Here, we present an iron-catalyzed asymmetric three-component radical carboazidation that processes electron-deficient alkenes by direct activation of aliphatic C–H bonds. This strategy provides access to a range of valuable chiral azides from readily available chemical feedstocks bearing a tetrasubstituted carbon stereocenter, and their synthetic potential is further showcased through straightforward transformations to provide other valuable enantioenriched building blocks.

Key words

carboazidation - hydrocarbons - ligands - asymmetric synthesis - radical ligand transfer - trimethylsilyl azide


Publication History

Received: 21 May 2024

Accepted after revision: 25 June 2024

Accepted Manuscript online:
25 June 2024

Article published online:
17 July 2024

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