Issue 9, 2023

Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins

Abstract

Intermolecular carboamination of olefins offers a powerful platform for the rapid construction of structurally complex amines from abundant feedstocks. However, these reactions often require transition-metal catalysis, and are mainly limited to 1,2-carboamination. Herein, we report a novel radical relay 1,4-carboimination across two distinct olefins with alkyl carboxylic acid-derived bifunctional oxime esters via energy transfer catalysis. The reaction is highly chemo- and regioselective, and multiple C–C and C–N bonds were formed in a single orchestrated operation. This mild and metal-free method features a remarkably broad substrate scope with excellent tolerance of sensitive functional groups, therefore providing easy access to structurally diverse 1,4-carboiminated products. Moreover, the obtained imines could be easily converted into valuable biologically relevant free γ-amino acids.

Graphical abstract: Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins

Supplementary files

Article information

Article type
Edge Article
Submitted
24 Nov 2022
Accepted
03 Feb 2023
First published
03 Feb 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 2447-2454

Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins

G. Tan, F. Paulus, A. Petti, M. Wiethoff, A. Lauer, C. Daniliuc and F. Glorius, Chem. Sci., 2023, 14, 2447 DOI: 10.1039/D2SC06497A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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