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A Predictably Selective Palladium-Catalyzed Aliphatic C-H Oxygenation. / Lubov, Dmitry P; Shashkov, Mikhail V; Nefedov, Andrey A et al.

In: Organic Letters, Vol. 25, No. 9, 10.03.2023, p. 1359-1363.

Research output: Contribution to journal › Article › peer-review

Harvard

Lubov, DP, Shashkov, MV, Nefedov, AA & Bryliakov, KP 2023, 'A Predictably Selective Palladium-Catalyzed Aliphatic C-H Oxygenation', Organic Letters, vol. 25, no. 9, pp. 1359-1363. https://doi.org/10.1021/acs.orglett.2c04371

APA

Lubov, D. P., Shashkov, M. V., Nefedov, A. A., & Bryliakov, K. P. (2023). A Predictably Selective Palladium-Catalyzed Aliphatic C-H Oxygenation. Organic Letters, 25(9), 1359-1363. https://doi.org/10.1021/acs.orglett.2c04371

Vancouver

Lubov DP, Shashkov MV, Nefedov AA, Bryliakov KP. A Predictably Selective Palladium-Catalyzed Aliphatic C-H Oxygenation. Organic Letters. 2023 Mar 10;25(9):1359-1363. Epub 2023 Feb 24. doi: 10.1021/acs.orglett.2c04371

Author

Lubov, Dmitry P ; Shashkov, Mikhail V ; Nefedov, Andrey A et al. / A Predictably Selective Palladium-Catalyzed Aliphatic C-H Oxygenation. In: Organic Letters. 2023 ; Vol. 25, No. 9. pp. 1359-1363.

BibTeX

@article{4e6776f2bbe74de4bd7b4324aad45192,
title = "A Predictably Selective Palladium-Catalyzed Aliphatic C-H Oxygenation",
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.",
author = "Lubov, {Dmitry P} and Shashkov, {Mikhail V} and Nefedov, {Andrey A} and Bryliakov, {Konstantin P}",
note = "ACKNOWLEDGMENTS: The authors acknowledge funding from the Ministry of Science and Higher Education within the governmental orders for Boreskov Institute of Catalysis (project AAAA-A21-121011390008-4). K.P.B., D.P.L., and M.V.S. gratefully acknowledge the access to the facilities of the shared research center “National center of investigation of catalysts”, provided by Boreskov Institute of Catalysis. A.A.N. is grateful to the Ministry of Science and Higher Education, project 1021051503141-0-1.4.1 for Vorozhtsov Novosibirsk Institute of Organic Chemistry (HR-MS measurements).",
year = "2023",
month = mar,
day = "10",
doi = "10.1021/acs.orglett.2c04371",
language = "English",
volume = "25",
pages = "1359--1363",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "9",

}

RIS

TY - JOUR

T1 - A Predictably Selective Palladium-Catalyzed Aliphatic C-H Oxygenation

AU - Lubov, Dmitry P

AU - Shashkov, Mikhail V

AU - Nefedov, Andrey A

AU - Bryliakov, Konstantin P

N1 - ACKNOWLEDGMENTS: The authors acknowledge funding from the Ministry of Science and Higher Education within the governmental orders for Boreskov Institute of Catalysis (project AAAA-A21-121011390008-4). K.P.B., D.P.L., and M.V.S. gratefully acknowledge the access to the facilities of the shared research center “National center of investigation of catalysts”, provided by Boreskov Institute of Catalysis. A.A.N. is grateful to the Ministry of Science and Higher Education, project 1021051503141-0-1.4.1 for Vorozhtsov Novosibirsk Institute of Organic Chemistry (HR-MS measurements).

PY - 2023/3/10

Y1 - 2023/3/10

N2 - 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.

AB - 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.

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85149018856&origin=inward&txGid=1f5d9861a93718ee2ca8269ea9eb4de0

UR - https://www.mendeley.com/catalogue/1f7047ae-b52e-34a0-a1e4-f414ed9af641/

U2 - 10.1021/acs.orglett.2c04371

DO - 10.1021/acs.orglett.2c04371

M3 - Article

C2 - 36825896

VL - 25

SP - 1359

EP - 1363

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 9

ER -

ID: 44533846