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Singlet‐Oxygen Oxidation of 5‐Hydroxymethylfurfural in Continuous Flow
Author(s) -
Heugebaert Thomas S. A.,
Stevens Christian V.,
Kappe C. Oliver
Publication year - 2015
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201403182
Subject(s) - singlet oxygen , flow chemistry , chemistry , continuous flow , yield (engineering) , photosensitizer , butenolide , rose bengal , photochemistry , oxygen , organic chemistry , catalysis , materials science , physics , mechanics , metallurgy
Singlet‐oxygen oxidation of 5‐hydroxymethylfurfural (5‐HMF) was performed in continuous flow mode using rose Bengal as photosensitizer. The resulting butenolide (H 2 MF) was formed selectively in high yield. The procedure proved to be scalable and applicable to related bio‐based furfurals. Furthermore, preliminary data show that H 2 MF can be readily isomerized thermally to 5‐hydroxy‐4‐keto‐pentenoic acid oligomers.