Decatungstate-mediated C(sp3 )‒H Heteroarylation via Radical Polar Crossover in Batch and Flow

    • Ting Wana
    • Luca Capaldoa
    • Gabriele Laudadioa
    • Alexander V. Nyuchevb
    • Juan A. Rincónc
    • Pablo García-Losadac
    • Carlos Mateosc
    • Michael O. Frederickd
    • Manuel Nuñoe
    • Timothy Noël*a
    • aFlow Chemistry Group, Van ’t Hoff Institute for Molecular Sciences(HIMS), University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands
    • bDepartment of Organic Chemistry, Lobachevsky State University of Nizhny Novgorod Gagarina Avenue 23, 603950, Nizhny Novgorod, Russia
    • cCentro de Investigación Lilly S.A. Avda. de la Industria 30, Alcobendas-Madrid 28108, Spain.
    • dSmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, United States.
    • eVapourtec Ltd., Park Farm Business Centre, Fornham St Genevieve, Bury St Edmunds, Suffolk IP28 6TS, United Kingdom.

    Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp3)‒H functionalization of organic molecules. Herein, we report on the unprecedented combination of decatungstate hydrogen atom transfer photocatalysis with the oxidative Radical-Polar Crossover concept to access the direct netoxidative C(sp3)‒H heteroarylation. The present methodology demonstrates a high functional group tolerance (40 examples) and is scalable when using continuous-flow reactor technology. The developed protocol is also amenable to the late-stage functionalization of biologically relevant molecules such as stanozolol, (‒)-ambroxide, podophyllotoxin and dideoxyribose.

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