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Issue 21, 2019
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A visible-light mediated three-component radical process using dithiocarbamate anion catalysis

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Abstract

We report a photoinduced three-component radical process, which couples readily available alkyl chlorides, maleimides, and heteroaromatic fragments to rapidly generate complex chiral products with high diastereocontrol. This method generates radicals via an SN2-based photochemical catalytic mechanism, which is not reliant on the redox properties of the precursors. It therefore grants access to open-shell intermediates from substrates that would be incompatible with or inert to classical radical-generating strategies. The redox-neutral conditions of this process make it tolerant of redox-sensitive substrates and allow the installation of multiple biologically relevant heterocycles within the cascade products.

Graphical abstract: A visible-light mediated three-component radical process using dithiocarbamate anion catalysis

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Supplementary files

Article information


Submitted
18 Feb 2019
Accepted
28 Apr 2019
First published
30 Apr 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 5484-5488
Article type
Edge Article

A visible-light mediated three-component radical process using dithiocarbamate anion catalysis

S. Cuadros, M. A. Horwitz, B. Schweitzer-Chaput and P. Melchiorre, Chem. Sci., 2019, 10, 5484
DOI: 10.1039/C9SC00833K

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

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    [Original citation] - Published by The Royal Society of Chemistry.

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