Details

Autor(en) / Beteiligte

• Kurganskiy, Vladimir I.
• Ottenbacher, Roman V.
• Shashkov, Mikhail V.
• Talsi, Evgenii P.
• Samsonenko, Denis G.
• Bryliakov, Konstantin P.

Titel

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

Ist Teil von

• Organic letters, 2022-12, Vol.24 (48), p.8764-8768

Ort / Verlag

American Chemical Society

Erscheinungsjahr

2022

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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.