Manganese-Catalyzed Regioselective C–H Lactonization and Hydroxylation of Fatty Acids with H2O2

Herein, we report the direct selective C–H lactonization of fatty acids (C5–C16), catalyzed by manganese­(II) complexes bearing bis-amino-bis-pyridine ligands. The catalyst system uses the environmentally benign hydrogen peroxide as oxidant and exhibits high efficiency (100–200 TON), providing under...

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Bibliographic Details
Published in:Organic letters 2022-12, Vol.24 (48), p.8764-8768
Main Authors: Kurganskiy, Vladimir I., Ottenbacher, Roman V., Shashkov, Mikhail V., Talsi, Evgenii P., Samsonenko, Denis G., Bryliakov, Konstantin P.
Format: Article
Language:English
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Summary:Herein, we report the direct selective C–H lactonization of fatty acids (C5–C16), catalyzed by manganese­(II) complexes bearing bis-amino-bis-pyridine ligands. The catalyst system uses the environmentally benign hydrogen peroxide as oxidant and exhibits high efficiency (100–200 TON), providing under optimized conditions γ-lactones in 60–90% yields. Remarkably, by changing the reaction conditions, the oxidation of hexanoic acid can be diverted toward formation of δ-caprolactone in up to 67% yield. Furthermore, the possibility of obtaining (ω-1)-hydroxy derivatives from linear C7–C10 acids in up to 48% yields has been demonstrated.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03458