Verification of preparations of (1H-indol-3-yl)methyl electrophiles and development of their microflow rapid generation and substitution.

Authors

Hisashi Masui, Sena Kanda, Shinichiro Fuse

Published in

Communications chemistry. Volume 6. Issue 1. Pages 47. Mar 04, 2023. Epub Mar 04, 2023.

Abstract

Although highly reactive (1H-indol-3-yl)methyl electrophiles such as (1H-indol-3-yl)methyl halides are potential precursors for the synthesis of various indole derivatives, some researchers have reported difficulties in their preparation due to concomitant undesired dimerization/oligomerization. Nevertheless, there have been some reports on the preparation of (1H-indol-3-yl)methyl halides. To resolve this contradiction, all the previously reported preparations of (1H-indol-3-yl)methyl halides were examined. However, we could not reproduce any of these preparations, and we revised several structures of indole derivatives. Here we show the rapid (0.02 s) and mild (25 °C) generation of an (1H-indol-3-yl)methyl electrophile that enables the rapid (0.1 s) and mild (25 °C) nucleophilic substitution in a microflow reactor. Eighteen unprotected indole analogues can be successfully synthesized using the developed microflow nucleophilic substitution with various nucleophiles.

PMID:
36871078
Bibliographic data and abstract were imported from PubMed on 05 Mar 2023.

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