Photocatalytic Regioselective Redox-Neutral 1,3-Oxypyridylation of Aryl Cyclopropanes

Pyridines and cyclopropanes are important structural units in chemistry. Herein, we introduce a photoredox-catalyzed approach for the ring opening and 1,3-oxypyridylation of aryl cyclopropanes using 4-cyanopyridines and carboxylic acids. This sequential process involves single-electron oxidation of the aryl cyclopropane, leading to nucleophilic ring opening and radical pyridylation at the benzylic position. The redox-neutral reaction exhibits high regioselectivity under mild reaction conditions, offering a broad substrate scope and wide applicability.

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Publication Details

Journal
Organic Letters
Published
2024-09-16
DOI
https://doi.org/10.1021/acs.orglett.4c02918
Citations
10
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
2.50

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article

Photocatalytic Regioselective Redox-Neutral 1,3-Oxypyridylation of Aryl Cyclopropanes

Fei Pan, Yi Zhao, Dongjie Li, Xiaoai Liu et al.
10 citations
Organic Letters
Cyclopropane Reaction Mechanisms
2.50
article

Photocatalytic Regioselective Redox-Neutral 1,3-Oxypyridylation of Aryl Cyclopropanes

Fei Pan, Yi Zhao, Dongjie Li, Xiaoai Liu, You-Zhi Liao
article en
10 citations

Abstract

Pyridines and cyclopropanes are important structural units in chemistry. Herein, we introduce a photoredox-catalyzed approach for the ring opening and 1,3-oxypyridylation of aryl cyclopropanes using 4-cyanopyridines and carboxylic acids. This sequential process involves single-electron oxidation of the aryl cyclopropane, leading to nucleophilic ring opening and radical pyridylation at the benzylic position. The redox-neutral reaction exhibits high regioselectivity under mild reaction conditions, offering a broad substrate scope and wide applicability.

Organic LettersVol. 26(38)
Sichuan Normal University (CN)
National Natural Science Foundation of China, Department of Science and Technology of Sichuan Province
Clean water and sanitation
Openalex Percentile: Top 11%
Cyclopropane Reaction Mechanisms
2.50
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