Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 17, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202200322
Keywords
eosin; photocatalysis; ring expansion; 2-pyridones; gamma-lactams
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Funding
- European Regional Development Fund of the European Union
- Greek national funds through the Operational Program Competitiveness, Entrepreneurship and Innovation [T2EDK-02364]
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This study describes a new photocatalytic ring expansion reaction that converts gamma-lactams into 2-pyridones, inspired by a late-stage oxidation commonly observed in fungal metabolism. The reaction is highly powerful and can directly convert readily accessible furans into 2-pyridones through sequential photo-induced reactions (energy transfer and electron transfer).
A new photocatalytic ring expansion reaction that transforms gamma-lactams into 2-pyridones is described. The reaction is radical-triggered and was inspired by a late-stage oxidation commonly observed in fungal metabolism. The reaction is particularly powerful because it can be included in a one pot process which converts readily accessible furans directly into 2-pyridones through sequential photo-induced reactions (energy transfer and electron transfer). The study also unveiled unprecedented reactivity for the mild and metal-free photocatalyst eosin, wherein it is used to cleave a C-I bond activated only by an electron donor on the neighbouring carbon.
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