Literature DB >> 23202538

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

Masanori Tayu1, Kazuhiro Higuchi, Masato Inaba, Tomomi Kawasaki.   

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.

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Year:  2012        PMID： 23202538     DOI： 10.1039/c2ob26944a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  3 in total

1.  Cu-Catalyzed Oxidation of C2 and C3 Alkyl-Substituted Indole via Acyl Nitroso Reagents.

Authors:  Jun Zhang; Saeedeh Torabi Kohlbouni; Babak Borhan
Journal:  Org Lett       Date:  2018-12-21       Impact factor: 6.005

2.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

3.  High Site Selectivity in Electrophilic Aromatic Substitutions: Mechanism of C-H Thianthrenation.

Authors:  Fabio Juliá; Qianzhen Shao; Meng Duan; Matthew B Plutschack; Florian Berger; Javier Mateos; Chenxi Lu; Xiao-Song Xue; K N Houk; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2021-09-21       Impact factor: 15.419
  3 in total

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