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Publication - Professor Jonathan Clayden

    Transition Metal Free Cycloamination of Prenyl Carbamates and Ureas Promoted by Aryldiazonium Salts

    Citation

    Abrams, R, Lefebvre, Q & Clayden, J, 2018, ‘Transition Metal Free Cycloamination of Prenyl Carbamates and Ureas Promoted by Aryldiazonium Salts’. Angewandte Chemie - International Edition, vol 57., pp. 13587-13591

    Abstract

    Upon treatment with aryldiazonium salts, prenyl carbamates and ureas undergo redox-neutral azocycloamination. In general, N-aryl O-prenyl carbamates cyclize in a photocatalytic reaction with visible light and an organic dye. With electron-deficient diazonium salts, electronic matching with an electron-rich N-aryl substituent results in a reaction proceeding in the ground state, without either light or photocatalyst. Cyclic voltammetry suggests that this radical reaction is initiated by hydrogen-atom abstraction mediated by an aryl radical, followed by a radical addition cascade and proton-coupled hole propagation. The reaction proceeds at room temperature in short reaction times, and a range of functional groups is tolerated.

    Full details in the University publications repository