Ketone–olefin coupling reactions are powerful tools for the construction of C–C bonds. These reactions, despite their usefulness, typically require the use of stoichiometric or super stoichiometric amounts of metal reductants. An alternative route to these couplings has been through the use of photoredox catalysis. The low (i.e. more negative) reduction potentials of alkyl carbonyls, however, has limited previous photoredox methods to aromatic ketones and aldehydes. Herein, we report a mild, metal-free ketone–olefin coupling reaction utilizing an excited-state acridine radical super reductant as a photoredox catalyst. This method is tolerant to a wide range substrates, including both aromatic and alkyl carbonyls, and has shown success for both inter- and intra-molecular substrates.

Ketone-olefin coupling of aliphatic and aromatic carbonyls catalyzed by excited-state acridine radicals

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