C–H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow

    • Paul Dingwall a
    • Andreas Greb a
    • Lorène N. S. Crespin a
    • Ricardo Labes a
    • Biagia Musio a
    • Jian-Siang Poh a
    • Patrick Pasau b
    • David C. Blakemore c
    • Steven V. Ley *a
    • a Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.
    • b UCB Biopharma SPRL, Chemical Research R5, Chemin du Foriest 1420, Braine-L’Alleud, Belgium
    • c Medicine Design, Pfizer Inc., Eastern Point Road, Groton, Connecticut 06340, USA

    The difficulty in accessing and safely utilising non-stabilised diazo species has in the past limited the application of this class of compounds. Here we explore further the use of oxadiazolines, non-stabilised diazo precursors which are bench stable, in direct, non-catalytic, aldehyde C–H functionalisation reactions under UV photolysis in flow and free from additives. Commercially available aldehydes are coupled to afford unsymmetrical aryl–alkyl and alkyl–alkyl ketones while mild conditions and lack of transition metal catalysts allow for exceptional functional group tolerance. Examples are given on small scale and in a larger scale continuous production.

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