Sulfoxide-TFAA and nucleophile combination as new reagent for aliphatic C-H functionalization at indole 2α-positionThis work is dedicated to Dr Masanori Sakamoto, Professor Emeritus of Meiji Pharmaceutical University, on the occasion of his 77th birthday (KIJU).Electronic supplementary information (ESI) available: General synthetic procedures and NMR data of compounds. See DOI: 10.1039/c2ob26944a

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. Esp...

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Main Authors: Tayu, Masanori, Higuchi, Kazuhiro, Inaba, Masato, Kawasaki, Tomomi
Format: Article
Language:English
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Summary: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. Aliphatic C-H functionalization at indole 2α-position mediated by acyloxythionium species generated from sulfoxide and TFAA has been developed. This reaction enables the introduction of O -, N - and C - substituents in a one-pot procedure.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob26944a