Photocatalytic\nRegioselective Redox-Neutral 1,3-Oxypyridylation\nof Aryl Cyclopropanes

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

Publication Details

Journal
Figshare
Published
2024-09-16
DOI
https://doi.org/10.1021/acs.orglett.4c02918.s001
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Photocatalytic\nRegioselective Redox-Neutral 1,3-Oxypyridylation\nof Aryl Cyclopropanes

Figshare
Radical Photochemical Reactions
article

Photocatalytic\nRegioselective Redox-Neutral 1,3-Oxypyridylation\nof Aryl Cyclopropanes

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Abstract

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

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Radical Photochemical Reactions
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Photocatalytic\nRegioselective Redox-Neutral 1,3-Oxypyridylation\nof Aryl Cyclopropanes · Figshare (2024) | TGRS Research Map | TGRS