The vast majority of photoredox protocols reported to date have been redox-neutral transformations. A smaller, though still substantial, number of net-reductive methods have also been reported, relying on the ready availability of practical reductants such as Hantzsch esters and tertiary amines. In contrast, general strategies for <i>net-oxidative</i> photoredox catalysis have developed much more slowly, primarily due to the scarcity of compatible co-oxidants. The most successful strategies reported to date are group transfer reactions, in which a portion of the terminal oxidant is incorporated into the final product. We have now developed an “oxidase” type strategy in which Cu(II) salts, used in concert with highly oxidizing organic photocatalysts, can effect the oxyamination of a broad range of styrenes. Key to the success of this method is the ability of Cu(II) to efficiently oxidize transient alkyl radical intermediates while not interfering with crucial photochemical processes.

Alkene oxyamination by net-oxidative photoredox catalysis

256th National Meeting (2018)

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