A Predictably Selective Palladium-Catalyzed Aliphatic C–H Oxygenation Full article
| Journal |
Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052 |
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| Output data | Year: 2023, Volume: 25, Number: 9, Pages: 1359–1363 Pages count : 5 DOI: 10.1021/acs.orglett.2c04371 | ||||||
| Tags | BOND FUNCTIONALIZATION; OXIDATIVE PROCESSES; NONHEME IRON; HYDROXYLATION; H2O2; COMPLEXES; MECHANISM | ||||||
| Authors |
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| Affiliations |
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Funding (2)
| 1 | Ministry of Science and Higher Education of the Russian Federation | 0239-2021-0009 |
| 2 | Ministry of Science and Higher Education of the Russian Federation | 0238-2021-0005 (АААА-А21-121011490018-2) |
Abstract:
Direct oxygenation of nonactivated aliphatic C(sp3)–H groups with peroxycarboxylic acids in the presence of palladium tris(pyridylmethyl)amine complex (0.6 mol %) is reported, providing the corresponding hydroxylated derivatives in up to 94% yields. The oxidation of 3° C–H groups occurs stereospecifically, with the catalyst system demonstrating extremely high sensitivity to electronic effects (adamantane oxidation: 3°:2° up to >300). This suggests potential applications for the 3°-regioselective oxidative functionalization of complex molecules of natural origin.
Cite:
Lubov D.P.
, Shashkov M.V.
, Nefedov A.A.
, Bryliakov K.P.
A Predictably Selective Palladium-Catalyzed Aliphatic C–H Oxygenation
Organic Letters. 2023. V.25. N9. P.1359–1363. DOI: 10.1021/acs.orglett.2c04371 WOS Scopus РИНЦ OpenAlex AN PMID
A Predictably Selective Palladium-Catalyzed Aliphatic C–H Oxygenation
Organic Letters. 2023. V.25. N9. P.1359–1363. DOI: 10.1021/acs.orglett.2c04371 WOS Scopus РИНЦ OpenAlex AN PMID
Dates:
| Submitted: | Dec 30, 2022 |
| Published online: | Feb 24, 2023 |
| Published print: | Mar 10, 2023 |
Identifiers:
| ≡ Web of science: | WOS:000938489000001 |
| ≡ Scopus: | 2-s2.0-85149018856 |
| ≡ Elibrary: | 53845754 |
| ≡ OpenAlex: | W4321748450 |
| ≡ Chemical Abstracts: | 2023:387469 |
| ≡ PMID: | 36825896 |