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Methylene Blue as a Photosensitizer and Redox Agent: Synthesis of 5‐Hydroxy‐1 H ‐pyrrol‐2(5 H )‐ones from Furans
Author(s) -
Kalaitzakis Dimitris,
Kouridaki Antonia,
Noutsias Dimitris,
Montag Tamsyn,
Vassilikogiannakis Georgios
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201500744
Subject(s) - methylene blue , singlet oxygen , photosensitizer , redox , context (archaeology) , methylene , combinatorial chemistry , chemistry , photochemistry , oxygen , organic chemistry , catalysis , photocatalysis , paleontology , biology
A highly efficient and general singlet‐oxygen‐initiated one‐pot transformation of readily accessible furans into 5‐hydroxy‐1 H ‐pyrrol‐2(5 H )‐ones has been developed. The methodology was extended to the synthesis of other high‐value α,β‐unsaturated γ‐lactams. This useful set of transformations relies not only on the photosensitizing ability of methylene blue, but also on its redox properties: properties that have until now been virtually ignored in a synthetic context.