Visible light activation of Boronic Esters enables efficient photoredox C(sp2)–C(sp3) cross-couplings in flow

    Fabio Limaa, Dr. Mikhail A. Kabeshova, Dr. Duc N. Trana, Dr. Claudio Battilocchioa, Dr. Joerg Sedelmeierb, Dr. Gottfried Sedelmeierb, Dr. Berthold Schenkelb, S. V. Ley*a

    • * Corresponding author
    • a Department of Chemistry, University of Cambridge, Cambridge, UK
    • b Novartis Pharma AG, Basel, Switzerland

    We report herein a new method for the photoredox activation of boronic esters. Using these reagents, an efficient and high-throughput continuous flow process was developed to perform a dual iridium- and nickel-catalyzed C(sp2)–C(sp3) coupling by circumventing solubility issues associated with potassium trifluoroborate salts. Formation of an adduct with a pyridine-derived Lewis base was found to be essential for the photoredox activation of the boronic esters. Based on these results we were able to develop a further simplified visible light mediated C(sp2)–C(sp3) coupling method using boronic esters and cyano heteroarenes under flow conditions.

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