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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.
Original language | English |
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Pages (from-to) | 13587-13591 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 57 |
Issue number | 41 |
Early online date | 17 Sep 2018 |
DOIs | |
Publication status | Published - 8 Oct 2018 |
Keywords
- amination
- cyclizations
- diazonium salts
- heterocycles
- radicals
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Dive into the research topics of 'Transition Metal Free Cycloamination of Prenyl Carbamates and Ureas Promoted by Aryldiazonium Salts'. Together they form a unique fingerprint.Projects
- 1 Finished
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alpha-Arylation and alpha-Vinylation of Enolates: New Reactivity from the Urea Linkage.
1/07/15 → 31/05/18
Project: Research