Photosensitized\nThree-Component Carboimination of\nAlkenes Based on the Relay of Oxy Radicals to Carbon Radicals

Here, we present a metal-free photosensitized three-component\nreaction\nfor the carboimination of alkenes based on oxime carbonates. Homolysis\nof oxime carbonates via light-mediated energy transfer enables the\nsimultaneous generation of iminyl radicals and alkoxycarbonyloxyl\nradicals. The alkoxycarbonyloxyl and alkoxy radicals can act as an\neffective hydrogen atom transfer reagent, abstracting hydrogen atoms\nfrom alkanes and aldehydes, silanes, and phosphine oxide. This strategy\nexhibits broad functional group tolerance under mild reaction conditions,\nfurther broadening the diversity of alkene carboimination.

Publication Details

Journal
Figshare
Published
2024-10-21
DOI
https://doi.org/10.1021/acs.orglett.4c03247.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
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article
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article

Photosensitized\nThree-Component Carboimination of\nAlkenes Based on the Relay of Oxy Radicals to Carbon Radicals

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Mycorrhizal Fungi and Plant Interactions
article

Photosensitized\nThree-Component Carboimination of\nAlkenes Based on the Relay of Oxy Radicals to Carbon Radicals

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Abstract

Here, we present a metal-free photosensitized three-component\nreaction\nfor the carboimination of alkenes based on oxime carbonates. Homolysis\nof oxime carbonates via light-mediated energy transfer enables the\nsimultaneous generation of iminyl radicals and alkoxycarbonyloxyl\nradicals. The alkoxycarbonyloxyl and alkoxy radicals can act as an\neffective hydrogen atom transfer reagent, abstracting hydrogen atoms\nfrom alkanes and aldehydes, silanes, and phosphine oxide. This strategy\nexhibits broad functional group tolerance under mild reaction conditions,\nfurther broadening the diversity of alkene carboimination.

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Photosensitized\nThree-Component Carboimination of\nAlkenes Based on the Relay of Oxy Radicals to Carbon Radicals · Figshare (2024) | TGRS Research Map | TGRS