Jump to main content
Jump to site search


A BF3·Et2O catalyzed atom-economical approach to highly substituted indole-3-carbinols from nitrosobenzenes and propargylic alcohols

Author affiliations

Abstract

The BF3·Et2O catalyzed reaction of nitrosobenzenes and an excess amount of propargylic alcohols was investigated to synthesize highly-substituted indole-3-carbinols. This reaction involves formal [3 + 2]-cycloaddition and the subsequent 1,3-rearrangement in a tandem manner via 3-alkylidene-3H-indole N-oxides. This methodology involves the sequential addition of propargylic alcohols and inexpensive Lewis acid catalyst, occurs in an open-air environment and is atom economical. The highly-substituted indole-3-carbinols were obtained in short time and the operational simplicity allows for a large scale experiment.

Graphical abstract: A BF3·Et2O catalyzed atom-economical approach to highly substituted indole-3-carbinols from nitrosobenzenes and propargylic alcohols

Back to tab navigation

Supplementary files

Publication details

The article was received on 16 Oct 2017, accepted on 21 Dec 2017 and first published on 21 Dec 2017


Article type: Paper
DOI: 10.1039/C7OB02559A
Citation: Org. Biomol. Chem., 2018, Advance Article
  •   Request permissions

    A BF3·Et2O catalyzed atom-economical approach to highly substituted indole-3-carbinols from nitrosobenzenes and propargylic alcohols

    S. Muthusamy, A. Balasubramani and E. Suresh, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02559A

Search articles by author

Spotlight

Advertisements