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 |
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| Output data | Year: 2022, Volume: 24, Number: 48, Pages: 8764-8768 Pages count : 5 DOI: 10.1021/acs.orglett.2c03458 | ||||||
| Tags | Catalysts, Lipids, Organic acids, Selectivity, Transition metals | ||||||
| Authors |
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| Affiliations |
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Funding (2)
| 1 | Russian Science Foundation | 20-13-00032 (АААА-А20-120071590003-2) |
| 2 | Ministry of Science and Higher Education of the Russian Federation | FWUZ-2021-0001 (121031700321-3) |
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.
Cite:
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 AN PMID OpenAlex
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 AN PMID OpenAlex
Dates:
| Submitted: | Oct 11, 2022 |
| Published online: | Nov 30, 2022 |
Identifiers:
| Web of science: | WOS:000892107800001 |
| Scopus: | 2-s2.0-85143537398 |
| Elibrary: | 50357022 |
| Chemical Abstracts: | 2022:3019479 |
| PMID: | 36450152 |
| OpenAlex: | W4310483853 |