PhotocatalyticPyridyl-carbamoylation of Alkenes forAccessing 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.

Publication Details

Journal
Figshare
Published
2025-03-07
DOI
https://doi.org/10.1021/acs.orglett.5c00195.s001
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

PhotocatalyticPyridyl-carbamoylation of Alkenes forAccessing β‑Pyridyl Amides

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Radical Photochemical Reactions
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PhotocatalyticPyridyl-carbamoylation of Alkenes forAccessing β‑Pyridyl Amides

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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.

Figshare
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Radical Photochemical Reactions
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PhotocatalyticPyridyl-carbamoylation of Alkenes forAccessing β‑Pyridyl Amides · Figshare (2025) | TGRS Research Map | TGRS