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.
CITATION STYLE
Kurganskiy, V. I., Ottenbacher, R. V., Shashkov, M. V., Talsi, E. P., Samsonenko, D. G., & Bryliakov, K. P. (2022). Manganese-Catalyzed Regioselective C-H Lactonization and Hydroxylation of Fatty Acids with H2O2. Organic Letters, 24(48), 8764–8768. https://doi.org/10.1021/acs.orglett.2c03458
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