Photocatalytic Pyridyl-carbamoylation of Alkenes for Accessing β-Pyridyl Amides

The β-pyridyl amide is a critical scaffold in medical discovery yet lacks efficient synthetic methods. Here, we describe, for the first time, a visible-light-induced, redox-neutral radical cross-coupling reaction involving alkenes, oxamic acids, and cyanopyridines that offers a versatile assembly of β-pyridylamides. This approach features mild reaction conditions, high step efficiency, and substrate breadth, providing a green and efficient strategy for alkene pyridyl-carbamoylation. Achieving this transformation relies on the efficient catalytic system, which adeptly avoids the competing cross-coupling of the nucleophilic carbamoyl radical with the electrophilic pyridyl radical, enabling the three-component radical tandem reaction process with high chemoselectivity.

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Publication Details

Journal
Organic Letters
Published
2025-03-07
DOI
https://doi.org/10.1021/acs.orglett.5c00195
Citations
9
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
7.25

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article

Photocatalytic Pyridyl-carbamoylation of Alkenes for Accessing β-Pyridyl Amides

Weijie Yu, Jie Wu, Yilin Zhu, Shaoyu Li et al.
9 citations
Organic Letters
Chemical Synthesis and Analysis
7.25
article

Photocatalytic Pyridyl-carbamoylation of Alkenes for Accessing β-Pyridyl Amides

Weijie Yu, Jie Wu, Yilin Zhu, Shaoyu Li, Jian Cui, Zhikai Li, Yun Mao
article en
9 citations

Abstract

The β-pyridyl amide is a critical scaffold in medical discovery yet lacks efficient synthetic methods. Here, we describe, for the first time, a visible-light-induced, redox-neutral radical cross-coupling reaction involving alkenes, oxamic acids, and cyanopyridines that offers a versatile assembly of β-pyridylamides. This approach features mild reaction conditions, high step efficiency, and substrate breadth, providing a green and efficient strategy for alkene pyridyl-carbamoylation. Achieving this transformation relies on the efficient catalytic system, which adeptly avoids the competing cross-coupling of the nucleophilic carbamoyl radical with the electrophilic pyridyl radical, enabling the three-component radical tandem reaction process with high chemoselectivity.

Organic LettersVol. 27(11)
Taizhou University (CN)
National Natural Science Foundation of China, Science and Technology Plan Project of Taizhou, Natural Science Foundation of Zhejiang Province
Openalex Percentile: Top 3%
Chemical Synthesis and Analysis
7.25
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Photocatalytic Pyridyl-carbamoylation of Alkenes for Accessing β-Pyridyl Amides — Weijie Yu, Jie Wu, et al. · Organic Letters (2025) | TGRS Research Map | TGRS