Photosensitized Three-Component Carboimination of Alkenes Based on the Relay of Oxy Radicals to Carbon Radicals.

Org Lett

State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, P. R. China.

Published: November 2024


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Article Abstract

Here, we present a metal-free photosensitized three-component reaction for the carboimination of alkenes based on oxime carbonates. Homolysis of oxime carbonates via light-mediated energy transfer enables the simultaneous generation of iminyl radicals and alkoxycarbonyloxyl radicals. The alkoxycarbonyloxyl and alkoxy radicals can act as an effective hydrogen atom transfer reagent, abstracting hydrogen atoms from alkanes and aldehydes, silanes, and phosphine oxide. This strategy exhibits broad functional group tolerance under mild reaction conditions, further broadening the diversity of alkene carboimination.

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http://dx.doi.org/10.1021/acs.orglett.4c03247DOI Listing

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