Sonochemistry: An efficient alternative to the synthesis of 3-selanylindoles using CuI as catalyst

Beatriz M Vieira; Samuel Thurow; Juliana S Brito; Gelson Perin; Diego Alves; Raquel G Jacob; Claudio Santi; Eder J Lenardão

doi:10.1016/j.ultsonch.2015.05.012

Sonochemistry: An efficient alternative to the synthesis of 3-selanylindoles using CuI as catalyst

Ultrason Sonochem. 2015 Nov:27:192-199. doi: 10.1016/j.ultsonch.2015.05.012. Epub 2015 May 22.

Authors

Beatriz M Vieira¹, Samuel Thurow², Juliana S Brito³, Gelson Perin⁴, Diego Alves⁵, Raquel G Jacob⁶, Claudio Santi⁷, Eder J Lenardão⁸

Affiliations

¹ Laboratório de Síntese Orgânica Limpa - LASOL, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil. Electronic address: biamvieira14@hotmail.com.
² Laboratório de Síntese Orgânica Limpa - LASOL, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil. Electronic address: samuelthurowdoug@gmail.com.
³ Laboratório de Síntese Orgânica Limpa - LASOL, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil. Electronic address: julianabrit@gmail.com.
⁴ Laboratório de Síntese Orgânica Limpa - LASOL, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil. Electronic address: gelson_perin@ufpel.edu.br.
⁵ Laboratório de Síntese Orgânica Limpa - LASOL, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil. Electronic address: diego.alves@ufpel.edu.br.
⁶ Laboratório de Síntese Orgânica Limpa - LASOL, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil. Electronic address: raquel.jacob@ufpel.edu.br.
⁷ Dipartimento di Chimica e Tecnologia del Farmaco, Group of Catalysis and Green Chemistry, Università degli Studi di Perugia, Perugia, Italy. Electronic address: claudio.santi@unipg.it.
⁸ Laboratório de Síntese Orgânica Limpa - LASOL, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil. Electronic address: lenardao@ufpel.edu.br.

PMID: 26186837
DOI: 10.1016/j.ultsonch.2015.05.012

Abstract

Ultrasonic (US) irradiation was successfully used as an alternative energy source to prepare 3-selanylindoles through the direct selanylation of indoles with diorganyl diselenides using CuI (20 mol%) as catalyst and DMSO as the solvent. By using this US-promoted reaction, eleven 3-organylselanylindoles were prepared selectively and in good yields. A comparative study between the reactions under conventional heating, microwave and ultrasound irradiations was performed, and it was observed advantage in using US over the other heating systems.

Keywords: 3-Arylselanylindoles; Copper-catalysis; Green chemistry; Organoselenium; Sonochemistry.

Publication types

Research Support, Non-U.S. Gov't