Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 22, Pages 6678-6686Publisher
WILEY-BLACKWELL
DOI: 10.1002/chem.200903284
Keywords
automated synthesis; continuous flow; continuous liquid liquid extraction; indoles; microreactors
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Funding
- The Irish Research Council for Science, Engineering and Technology
- Schering-Plough (Avondale)
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An automated sequential approach for the generation and reactions of 3-hydroxymethylindoles in continuous-flow microreactors is described. Consecutive halogen magnesium exchanges of four 3-iodoindoles followed by addition to three aldehydes provided twelve 3-hydroxymethylindoles in a multi-microreactor setup. The synthetic flow strategy could be coupled with an in line continuous liquid liquid extraction workup protocol for each reaction. Further elaboration of each of these in-doles within the fluidic setup was achieved by acid-catalysed nucleophilic substitutions with allyltrimethylsilane and methanol used as nucleophiles. Overall, a set of four 3-iodoindoles was converted into thirty-six indole derivatives by a range of transformations including iodo magnesium exchange/electrophile trapping and acid-catalysed nucleophilic substitution in a fully automated sequential fashion.
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