Issue 21, 2019

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
18 Febr. 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
Creative Commons BY-NC license

Chem. Sci., 2019,10, 5484-5488

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

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