Photoredox-Catalyzed Dehydrogenative Csp3–Csp2 Cross-Coupling of Alkylarenes to Aldehydes in Flow

    • Oliver M. Griffithsa
    • Henrique A. Estevesa
    • Yiding Chena
    • Karin Sowaa,b
    • Oliver S. Maya
    • Peter Morsec
    • David C. Blakemorec
    • Steven V. Ley*a
    • aYusuf Hamied Department of Chemistry, University of Cambridge, CB2 1EW Cambridge, U.K.
    • bDepartment of Chemistry, University of Münster, 48149 Münster, Germany
    • cMedicine Design, Pfizer, Inc., Groton, Connecticut 06340, United States

    Executing photoredox reactions in flow offers solutions to frequently encountered issues regarding reproducibility, reaction time, and scale-up. Here, we report the transfer of a photoredox-catalyzed benzylic coupling of alkylarenes to aldehydes to a flow chemistry setting leading to improvements in terms of higher concentration, shorter residence times, better yields, ease of catalyst preparation, and enhanced substrate scope. Its applicability has been demonstrated by a multi-gram-scale reaction using high-power light-emitting diodes (LEDs), late-stage functionalization of selected active pharmaceutical ingredients (APIs), and also a photocatalyst recycling method.

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