Amidines as potent nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes |
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| Authors: | Simon M Ahmad Gemma Cansell Joanna M Redmond |
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| Institution: | a Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK
b GlaxoSmithKline Ltd, Medicines Research Centre, Gunnels Wood Road, Stevenage SG1 2NY, UK |
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| Abstract: | (±)-iso-Amarine is a potent organocatalyst at 1 mol % loading for both the bromoacetoxylation of alkenes with added acetic acid and bromolactonisation of unsaturated carboxylic acids with stoichiometric NBS as the electrophilic bromine source. A simple bromoamidine with an N-Br bond has been characterised crystallographically for the first time. Asymmetric induction in the bromination reactions with enantiopure amidines was zero. |
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| Keywords: | Electrophilic bromination Alkenes Organocatalysis Amidine |
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