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Updated: Jun 13, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
Automated generation and reactions of 3-hydroxymethylindoles in continuous-flow microreactors
Thomas Tricotet1, Donal F O'Shea
1Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland.
Abstract:
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 indoles 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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