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

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
Pages (from-to)	5299-5305
Number of pages	7
Journal	Organic Letters
Volume	27
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.5c01577
State	Published - 23 May 2025
Externally published	Yes

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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.",

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

language = "英语",

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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 - 2025/5/23

Y1 - 2025/5/23

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.

UR - http://www.scopus.com/inward/record.url?scp=105005432146&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5c01577

DO - 10.1021/acs.orglett.5c01577

M3 - 文章

AN - SCOPUS:105005432146

SN - 1523-7060

VL - 27

SP - 5299

EP - 5305

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

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

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