Literature DB >> 24890610

Indole synthesis based on a modified Koser reagent.

Laura Fra1, Alba Millán, José A Souto, Kilian Muñiz.   

Abstract

A new metal-free method for the rapid and productive preparation of indoles has been developed. This process is based on sterically congested hypervalent iodine compounds of the family of Koser reagents, and iodosobenzene in combination with 2,4,5-tris-isopropylbenzene sulfonic acid provides the highest yields and fastest reaction times. This reagent alone promotes the chemoselective oxidative cyclization of 2-amino styrenes to indoles in high yields under mild conditions.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amination; catalysis; hypervalent iodine; indole; oxidation

Mesh:

Substances:

Year:  2014        PMID: 24890610     DOI: 10.1002/anie.201402661

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  5 in total

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Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Synlett       Date:  2014       Impact factor: 2.454

2.  Interrupted Intramolecular Hydroaminomethylation of N-Protected-2-vinyl Anilines: Novel Access to 3-Substitued Indoles or Indoline-2-ols.

Authors:  Frank Hochberger-Roa; Perla H García-Ríos; José G López-Cortés; M Carmen Ortega-Alfaro; Jean-Claude Daran; Maryse Gouygou; Martine Urrutigoïty
Journal:  Molecules       Date:  2022-02-05       Impact factor: 4.411

3.  Titanocene(III)-Catalyzed Precision Deuteration of Epoxides.

Authors:  Dina Schwarz G Henriques; Elena Rojo-Wiechel; Sven Klare; Regine Mika; Sebastian Höthker; Jonathan H Schacht; Niklas Schmickler; Andreas Gansäuer
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-21       Impact factor: 16.823

4.  Sterically Congested 2,6-Disubstituted Anilines from Direct C-N Bond Formation at an Iodine(III) Center.

Authors:  Nicola Lucchetti; Michelangelo Scalone; Serena Fantasia; Kilian Muñiz
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

5.  Synthesis of Azacarbolines via PhIO2-Promoted Intramolecular Oxidative Cyclization of α-Indolylhydrazones.

Authors:  Matteo Corrieri; Lucia De Crescentini; Fabio Mantellini; Giacomo Mari; Stefania Santeusanio; Gianfranco Favi
Journal:  J Org Chem       Date:  2021-12-06       Impact factor: 4.354

  5 in total

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