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

被引:59
作者
Kollmann, Jiri [1 ]
Zhang, Yu [1 ]
Schilling, Waldemar [1 ]
Zhang, Tong [1 ]
Riemer, Daniel [1 ]
Das, Shoubhik [1 ]
机构
[1] Georg August Univ Gottingen, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany
关键词
RADICAL-CATION; ENANTIOSELECTIVE SYNTHESIS; PHOTOREDOX CATALYSIS; 2+2 CYCLOADDITION; COMPLEXES; OXIDATION; ALCOHOLS; 2,3-DIHYDROPYRIDIN-4(1H)-ONES; PHOTOCATALYSIS; DERIVATIVES;
D O I
10.1039/c9gc00485h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
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页码:1916 / 1920
页数:5
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