Cobalt-Catalyzed Regio- and Stereoselective C(sp2)-H Alkylation of Enamides with 4-Alkyl-1,4-dihydropyridines

Meng Wei Sheng; Meng Liang Deng; Xu Kang Wen; Meng Yang Wang; Meng Ting Chu; Teck Peng Loh; Ming Zhu Lu

doi:10.1021/acs.orglett.5c01577

Cobalt-Catalyzed Regio- and Stereoselective C(sp²)-H Alkylation of Enamides with 4-Alkyl-1,4-dihydropyridines

Meng Wei Sheng, Meng Liang Deng, Xu Kang Wen, Meng Yang Wang, Meng Ting Chu, Teck Peng Loh^*, Ming Zhu Lu^*

^*Corresponding author for this work

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

Abstract

We report herein an efficient cobalt-catalyzed regioselective and stereoselective alkenyl C(sp²)-H alkylation of structurally diverse enamides with 4-alkyl-1,4-dihydropyridines (DHPs) as the alkyl radical precursors. This DHPs-based approach features a broad substrate scope and excellent compatibility with diverse functionalities, giving rise to geometrically defined β-alkylated enamides with an exclusive E configuration. Preliminary mechanistic studies suggest a radical-involved pathway.

Original language	English
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.5c01577
Publication status	Accepted/In press - 2025
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2025 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.5c01577

Cite this

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title = "Cobalt-Catalyzed Regio- and Stereoselective C(sp2)-H Alkylation of Enamides with 4-Alkyl-1,4-dihydropyridines",

abstract = "We report herein an efficient cobalt-catalyzed regioselective and stereoselective alkenyl C(sp2)-H alkylation of structurally diverse enamides with 4-alkyl-1,4-dihydropyridines (DHPs) as the alkyl radical precursors. This DHPs-based approach features a broad substrate scope and excellent compatibility with diverse functionalities, giving rise to geometrically defined β-alkylated enamides with an exclusive E configuration. Preliminary mechanistic studies suggest a radical-involved pathway.",

author = "Sheng, {Meng Wei} and Deng, {Meng Liang} and Wen, {Xu Kang} and Wang, {Meng Yang} and Chu, {Meng Ting} and Loh, {Teck Peng} and Lu, {Ming Zhu}",

note = "Publisher Copyright: {\textcopyright} 2025 American Chemical Society.",

year = "2025",

doi = "10.1021/acs.orglett.5c01577",

language = "English",

journal = "Organic Letters",

issn = "1523-7060",

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T1 - Cobalt-Catalyzed Regio- and Stereoselective C(sp2)-H Alkylation of Enamides with 4-Alkyl-1,4-dihydropyridines

AU - Sheng, Meng Wei

AU - Deng, Meng Liang

AU - Wen, Xu Kang

AU - Wang, Meng Yang

AU - Chu, Meng Ting

AU - Loh, Teck Peng

AU - Lu, Ming Zhu

PY - 2025

Y1 - 2025

N2 - We report herein an efficient cobalt-catalyzed regioselective and stereoselective alkenyl C(sp2)-H alkylation of structurally diverse enamides with 4-alkyl-1,4-dihydropyridines (DHPs) as the alkyl radical precursors. This DHPs-based approach features a broad substrate scope and excellent compatibility with diverse functionalities, giving rise to geometrically defined β-alkylated enamides with an exclusive E configuration. Preliminary mechanistic studies suggest a radical-involved pathway.

AB - We report herein an efficient cobalt-catalyzed regioselective and stereoselective alkenyl C(sp2)-H alkylation of structurally diverse enamides with 4-alkyl-1,4-dihydropyridines (DHPs) as the alkyl radical precursors. This DHPs-based approach features a broad substrate scope and excellent compatibility with diverse functionalities, giving rise to geometrically defined β-alkylated enamides with an exclusive E configuration. Preliminary mechanistic studies suggest a radical-involved pathway.

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U2 - 10.1021/acs.orglett.5c01577

DO - 10.1021/acs.orglett.5c01577

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JF - Organic Letters

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