Issue 3, 2013
From the journal:

Organic & Biomolecular Chemistry

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

Masanori Tayu,a   Kazuhiro Higuchi,*a   Masato Inabaa  and  Tomomi Kawasaki*a  

* Corresponding authors

a Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan
E-mail: kawasaki@my-pharm.ac.jp, khiguchi@my-pharm.ac.jp
Fax: +81 42 495 8763
Tel: +81 42 495 8763

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

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Article information

DOI
https://doi.org/10.1039/C2OB26944A
Article type
Paper
Submitted
04 Oct 2012
Accepted
07 Nov 2012
First published
07 Nov 2012

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

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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

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