A Predictably Selective Palladium-Catalyzed Aliphatic C-H Oxygenation

Dmitry P Lubov; Mikhail V Shashkov; Andrey A Nefedov; Konstantin P Bryliakov

doi:10.1021/acs.orglett.2c04371

A Predictably Selective Palladium-Catalyzed Aliphatic C-H Oxygenation

Dmitry P Lubov, Mikhail V Shashkov, Andrey A Nefedov, Konstantin P Bryliakov

Результат исследования: Научные публикации в периодических изданиях › статья › рецензирование

Аннотация

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.

Язык оригинала	английский
Страницы (с-по)	1359-1363
Число страниц	5
Журнал	Organic Letters
Том	25
Номер выпуска	9
Ранняя дата в режиме онлайн	24 февр. 2023
DOI	https://doi.org/10.1021/acs.orglett.2c04371
Состояние	Опубликовано - 10 мар. 2023

Предметные области OECD FOS+WOS

1.06 БИОЛОГИЧЕСКИЕ НАУКИ
1.04 ХИМИЧЕСКИЕ НАУКИ

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10.1021/acs.orglett.2c04371

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

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@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",

}

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

В: Organic Letters, Том 25, № 9, 10.03.2023, стр. 1359-1363.

Результат исследования: Научные публикации в периодических изданиях › статья › рецензирование

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.mendeley.com/catalogue/1f7047ae-b52e-34a0-a1e4-f414ed9af641/

U2 - 10.1021/acs.orglett.2c04371

DO - 10.1021/acs.orglett.2c04371

M3 - Article

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VL - 25

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 9

ER -

A Predictably Selective Palladium-Catalyzed Aliphatic C-H Oxygenation

Аннотация

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