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

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

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2022, Volume: 24, Number: 48, Pages: 8764-8768 Pages count : 5 DOI: 10.1021/acs.orglett.2c03458

Authors

Kurganskiy Vladimir I. ¹ , Ottenbacher Roman V. ¹ , Shashkov Mikhail V. ^1,2 , Talsi Evgenii P. ² , Samsonenko Denis G. ³ , Bryliakov Konstantin P. ¹

Affiliations

1	Novosibirsk State University, Pirogova 1, Novosibirsk 630090, Russia
2	Boreskov Institute of Catalysis, Pr. Lavrentieva 5, Novosibirsk 630090, Russian Federation
3	Nikolaev Insitute of Inorganic Chemistry, Lavrentieva 3, Novosibirsk 630090, Russia

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.

Kurganskiy V.I. , Ottenbacher R.V. , Shashkov M.V. , Talsi E.P. , Samsonenko D.G. , Bryliakov K.P.
Manganese-Catalyzed Regioselective C–H Lactonization and Hydroxylation of Fatty Acids with H2O2
Organic Letters. 2022. V.24. N48. P.8764-8768. DOI: 10.1021/acs.orglett.2c03458 WOS Scopus РИНЦ OpenAlex

Submitted:	Oct 11, 2022
Published online:	Nov 30, 2022
Published print:	Dec 9, 2022

Web of science:	WOS:000892107800001
Scopus:	2-s2.0-85143537398
Elibrary:	50357022
OpenAlex:	W4310483853

DB	Citing
Web of science	14
Scopus	12
Elibrary	14
OpenAlex	14