Manganese-Catalyzed Regioselective C–H Lactonization and Hydroxylation of Fatty Acids with H2O2
Vladimir I Kurganskiy
1
,
MIKHAIL V. SHASHKOV
1, 2
,
Evgenii P. Talsi
2
,
Denis G. Samsonenko
1, 3
,
Publication type: Journal Article
Publication date: 2022-11-30
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
36450152
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
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.
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18
Total citations:
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Citations from 2025:
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(33.34%)
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GOST
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Kurganskiy V. I. et al. Manganese-Catalyzed Regioselective C–H Lactonization and Hydroxylation of Fatty Acids with H2O2 // Organic Letters. 2022. Vol. 24. No. 48. pp. 8764-8768.
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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. Vol. 24. No. 48. pp. 8764-8768.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.2c03458
UR - https://doi.org/10.1021/acs.orglett.2c03458
TI - Manganese-Catalyzed Regioselective C–H Lactonization and Hydroxylation of Fatty Acids with H2O2
T2 - Organic Letters
AU - Kurganskiy, Vladimir I
AU - Ottenbacher, Roman V
AU - SHASHKOV, MIKHAIL V.
AU - Talsi, Evgenii P.
AU - Samsonenko, Denis G.
AU - Bryliakov, Konstantin P.
PY - 2022
DA - 2022/11/30
PB - American Chemical Society (ACS)
SP - 8764-8768
IS - 48
VL - 24
PMID - 36450152
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2022_Kurganskiy,
author = {Vladimir I Kurganskiy and Roman V Ottenbacher and MIKHAIL V. SHASHKOV and Evgenii P. Talsi and Denis G. Samsonenko and Konstantin P. Bryliakov},
title = {Manganese-Catalyzed Regioselective C–H Lactonization and Hydroxylation of Fatty Acids with H2O2},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.orglett.2c03458},
number = {48},
pages = {8764--8768},
doi = {10.1021/acs.orglett.2c03458}
}
Cite this
MLA
Copy
Kurganskiy, Vladimir I., et al. “Manganese-Catalyzed Regioselective C–H Lactonization and Hydroxylation of Fatty Acids with H2O2.” Organic Letters, vol. 24, no. 48, Nov. 2022, pp. 8764-8768. https://doi.org/10.1021/acs.orglett.2c03458.