Photon Equivalents as a Parameter for Scaling Photoredox Reactions in Flow: Translation of Photocatalytic C−N Cross‐Coupling from Lab Scale to Multikilogram Scale

    • Emily B. Corcoran*a
    • Jonathan P. McMullen*b
    • François Lévesqueb
    • Michael K. Wismerc
    • John R. Naberb
    • aProcess Research & Development, Merck & Co., Inc., Boston, MA 02115 (USA)
    • bProcess Research & Development, Merck & Co., Inc., Rahway, NJ 07065 (USA)
    • cScientific Engineering & Design, Merck & Co., Inc., Kenilworth, NJ 07033 (USA)

    With the development of new photocatalytic methods over recent decades, the translation of these chemical reactions to industrial production scales using continuous flow reactors has become a topic of increasing interest.  In this context, we describe our studies toward elucidating an empirically‐derived parameter for scaling photocatalytic reactions in flow.  By evaluating the performance of a photocatalytic C‐N cross‐coupling across multiple reactor sizes and geometries, it was demonstrated that expressing product yield as a function of the absorbed photon equivalents provided a predictive, empirical scaling parameter.  Through the use of this scaling factor and characterization of the photonic flux within each reactor, the cross‐coupling was scaled successfully from milligram‐scale in batch to a multi‐kilogram reaction in flow.

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