A Predictably Selective Palladium-Catalyzed Aliphatic C–H Oxygenation | Sciact - CRIS-system of Boreskov Institute of Catalysis

A Predictably Selective Palladium-Catalyzed Aliphatic C–H Oxygenation Full article

Journal

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

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

Lubov Dmitry P. ^1,2 , Shashkov Mikhail V. ¹ , Nefedov Andrey A. ^2,3 , Bryliakov Konstantin P. ^1,2

Affiliations

1	Boreskov Institute of Catalysis, Novosibirsk 630090, Russian Federation
2	Novosibirsk State University, Novosibirsk 630090, Russia
3	Vorozhtsov Novosibirsk Institute of Organic Chemistry, Novosibirsk 630090, Russia

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)

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.

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 AN PMID OpenAlex

Submitted:	Dec 30, 2022
Published online:	Feb 24, 2023
Published print:	Mar 10, 2023

Web of science:	WOS:000938489000001
Scopus:	2-s2.0-85149018856
Elibrary:	53845754
Chemical Abstracts:	2023:387469
PMID:	36825896
OpenAlex:	W4321748450

DB	Citing
Scopus	8
Web of science	8
Elibrary	7
OpenAlex	9