TY - JOUR
T1 - Manganese-Catalyzed Regioselective C-H Lactonization and Hydroxylation of Fatty Acids with H2O2
AU - Kurganskiy, Vladimir I.
AU - Ottenbacher, Roman V.
AU - Shashkov, Mikhail V.
AU - Talsi, Evgenii P.
AU - Samsonenko, Denis G.
AU - Bryliakov, Konstantin P.
N1 - Funding Information:
This work was supported by the Russian Science Foundation, project 20-13-00032 (for Novosibirsk State University). M.V.S. and E.P.T. gratefully acknowledge the access to the facilities of the shared research center “National center of investigation of catalysts”, provided by Boreskov Institute of Catalysis. D.G.S. acknowledges budget funding from the Ministry of Science and Higher Education of the Russian Federation for the Nikolaev Institute of Inorganic Chemistry SB RAS, project 121031700321-3 (X-ray measurements). The authors are grateful to Dr. Andrey A. Nefedov from Vorozhtsov Institute of Organic Chemistry for the HRMS measurements.
Publisher Copyright:
© 2022 American Chemical Society.
PY - 2022/12/9
Y1 - 2022/12/9
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85143537398&partnerID=8YFLogxK
UR - https://www.mendeley.com/catalogue/9f93838b-5e24-3630-978f-7c3a526fa7b1/
U2 - 10.1021/acs.orglett.2c03458
DO - 10.1021/acs.orglett.2c03458
M3 - Article
C2 - 36450152
AN - SCOPUS:85143537398
VL - 24
SP - 8764
EP - 8768
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 48
ER -