Iron-Catalyzed Three-Component Asymmetric Carboazidation of Alkenes with Alkanes and Trimethylsilyl Azide

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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