Issue 3, 2013

Sulfoxide-TFAA and nucleophile combination as new reagent for aliphatic C–H functionalization at indole 2α-position

Abstract

Aliphatic C–H functionalization at indole 2α-position mediated by acyloxythionium species 1 generated from sulfoxide and acid anhydride has been developed. The combination of sulfoxide and TFAA with O-, N- and C-nucleophiles enabled introduction of various substituents in a one-pot procedure. Especially on utilizing DMSO, the combination provided a practical and efficient method for the synthesis of a wide range of 2α-substituted indoles.

Graphical abstract: Sulfoxide-TFAA and nucleophile combination as new reagent for aliphatic C–H functionalization at indole 2α-position

Supplementary files

Article information

Article type
Paper
Submitted
04 Oct 2012
Accepted
07 Nov 2012
First published
07 Nov 2012

Org. Biomol. Chem., 2013,11, 496-502

Sulfoxide-TFAA and nucleophile combination as new reagent for aliphatic C–H functionalization at indole 2α-position

M. Tayu, K. Higuchi, M. Inaba and T. Kawasaki, Org. Biomol. Chem., 2013, 11, 496 DOI: 10.1039/C2OB26944A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements