Issue 8, 2019

A simple ketone as an efficient metal-free catalyst for visible-light-mediated Diels–Alder and aza-Diels–Alder reactions

Abstract

Diels–Alder reactions are highly effective between electron-rich dienes and electron-poor dienophiles. However, these reactions with electron-rich dienophiles are limited and require forcing conditions. Based on this, an efficient metal-free homogeneous system has been developed for the Diels–Alder reactions between electron-rich dienophiles and dienes under visible-light conditions. Additionally, this catalyst has shown excellent reactivity for aza-Diels–Alder reactions. This simple catalyst is commercially available, non-toxic, and cheap and has shown excellent reactivity which is comparable to and in some cases even better than the reported metal-based catalysts. Finally, the mechanism of this reaction has been proposed based on the experimental evidence.

Graphical abstract: A simple ketone as an efficient metal-free catalyst for visible-light-mediated Diels–Alder and aza-Diels–Alder reactions

Supplementary files

Article information

Article type
Communication
Submitted
07 Feb 2019
Accepted
08 Mar 2019
First published
08 Mar 2019
This article is Open Access
Creative Commons BY license

Green Chem., 2019,21, 1916-1920

A simple ketone as an efficient metal-free catalyst for visible-light-mediated Diels–Alder and aza-Diels–Alder reactions

J. Kollmann, Y. Zhang, W. Schilling, T. Zhang, D. Riemer and S. Das, Green Chem., 2019, 21, 1916 DOI: 10.1039/C9GC00485H

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