Flow photochemical Giese reaction via silane-mediated activation of alkyl bromides

    • Fabiola Faniniab, Alberto Luridianaa, Daniele Mazzarellaac, Antonella Ilenia Alfanoad, Perryvan der Heidea, Juan A. Rincóne, Pablo García-Losadae, Carlos Mateose, Michael O. Frederickf, Manuel Nuñog, Timothy Noëla
    • aFlow Chemistry Group, Van ’t Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam Science Park 904, 1098 XH Amsterdam, The Netherlands
    • bDepartment of Biomolecular Sciences, University of Urbino “Carlo Bo”, Piazza Rinascimento 6, I-61029 Urbino, Italy
    • cDepartment of Chemical Sciences, University of Padova Institution, Via Francesco Marzolo, 1, 35131 Padova, Italy
    • dDepartment of Pharmacy, Department of Excellence 2018-2022, School of Medicine and Surgery, University of Naples “Federico II”, Via D. Montesano 49, I-80131 Naples, Italy
    • eCentro de Investigación Lilly S.A., Avda. de la Industria 30, Alcobendas-Madrid 28108, Spain
    • fSmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, IN 46285, United States
    • gVapourtec Ltd. Park Farm Business Centre, Fornham St Genevieve, Bury St Edmunds, Suffolk IP28 6TS, United Kingdom

    Organic halides play a key role as building blocks in synthesis because of their low cost and wide availability. In recent years, halogen-atom transfer (XAT) has emerged as a reliable approach to exploit these substrates in radical processes. Herein, we report a hydroalkylation of electron-poor olefins using alkyl bromides based on a UVA-induced silane-mediated XAT reaction. Our protocol is operationally simple, displays a broad scope and does not require a photocatalyst. Flow technology was used to reduce the reaction times and scale the process. Notably, a two-step protocol, combining the XAT protocol with a subsequent Horner-Wadsworth-Emmons reaction, has been developed to enable the allylation of C(sp3)–Br bonds.

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