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

Masanori Tayu; Kazuhiro Higuchi; Masato Inaba; Tomomi Kawasaki

doi:10.1039/C2OB26944A

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Organic & Biomolecular Chemistry

Issue 3, 2013

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

Masanori Tayu,^a Kazuhiro Higuchi,*^a Masato Inaba^a and Tomomi Kawasaki*^a

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

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

DOI: 10.1039/C2OB26944A
Received 04 Oct 2012, Accepted 07 Nov 2012
First published online 07 Nov 2012

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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.

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

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