Selenium dioxide-promoted selective synthesis of mono- and bis-sulfenylindoles

Samuel Thurow; Filipe Penteado; Gelson Perin; Diego Alves; Claudio Santi; Bonifacio Monti; Carl H. Schiesser; Thiago Barcellos; Eder J. Lenardão

doi:10.1039/C8QO00360B

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Selenium dioxide-promoted selective synthesis of mono- and bis-sulfenylindoles†

Samuel Thurow,

^a Filipe Penteado,

^a Gelson Perin,

^a Diego Alves,

^a Claudio Santi,

^b Bonifacio Monti,

^b Carl H. Schiesser,

*^c Thiago Barcellos

^d and Eder J. Lenardão

*^a

Author affiliations

* Corresponding authors

^a Centro de Ciências Químicas, Farmacêuticas e de Alimentos Universidade Federal de Pelotas – UFPel, P.O. box 354, Pelotas, RS, Brazil
E-mail: lenardao@ufpel.edu.br

^b Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo, 1, Perugia, PG, Italy

^c Seleno Therapeutics Pty. Ltd, Brighton East, Victoria, Australia
E-mail: carl@selenotherapeutics.com

^d Laboratory of Biotechnology of Natural and Synthetic Products, Universidade de Caxias do Sul – UCS, Caxias do Sul, RS, Brazil

Abstract

A selective method for the preparation of mono- and bis-sulfenylindoles was developed using an oxidizing agent and the I₂/SeO₂ system as an efficient catalyst. The selectivity was controlled by varying the amount of SeO₂. This represents the first example of the application of SeO₂ in this type of selective chemistry.

This article is part of the themed collection: Organic Chemistry Frontiers HOT articles for 2018

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Article information

DOI: https://doi.org/10.1039/C8QO00360B
Article type: Research Article
Submitted: 07 Apr 2018
Accepted: 06 May 2018
First published: 07 May 2018

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Org. Chem. Front., 2018,5, 1983-1991

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Selenium dioxide-promoted selective synthesis of mono- and bis-sulfenylindoles

S. Thurow, F. Penteado, G. Perin, D. Alves, C. Santi, B. Monti, C. H. Schiesser, T. Barcellos and E. J. Lenardão, Org. Chem. Front., 2018, 5, 1983 DOI: 10.1039/C8QO00360B

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Organic Chemistry Frontiers

Selenium dioxide-promoted selective synthesis of mono- and bis-sulfenylindoles†

Abstract

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Selenium dioxide-promoted selective synthesis of mono- and bis-sulfenylindoles

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