Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by Oxone<sup>®</sup>
We describe herein an alternative transition-metal-free procedure to access 3,4-bis(butylselanyl)selenophenes and the so far unprecedented 3-(butylselanyl)-4-alkoxyselenophenes. The protocol involves the 5-<i>endo</i>-dig electrophilic cyclization of 1,3-diynes promoted by electrophilic...
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doaj-50025e07a3044fb4beb2119d560348322021-04-19T23:04:58ZengMDPI AGMolecules1420-30492021-04-01262378237810.3390/molecules26082378Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by Oxone<sup>®</sup>Paola S. Hellwig0Jonatan S. Guedes1Angelita M. Barcellos2Gelson Perin3Eder J. Lenardão4LASOL—CCQFA, Universidade Federal de Pelotas—UFPel, P.O. Box 354, Pelotas 96010-900, RS, BrazilLASOL—CCQFA, Universidade Federal de Pelotas—UFPel, P.O. Box 354, Pelotas 96010-900, RS, BrazilLASOL—CCQFA, Universidade Federal de Pelotas—UFPel, P.O. Box 354, Pelotas 96010-900, RS, BrazilLASOL—CCQFA, Universidade Federal de Pelotas—UFPel, P.O. Box 354, Pelotas 96010-900, RS, BrazilLASOL—CCQFA, Universidade Federal de Pelotas—UFPel, P.O. Box 354, Pelotas 96010-900, RS, BrazilWe describe herein an alternative transition-metal-free procedure to access 3,4-bis(butylselanyl)selenophenes and the so far unprecedented 3-(butylselanyl)-4-alkoxyselenophenes. The protocol involves the 5-<i>endo</i>-dig electrophilic cyclization of 1,3-diynes promoted by electrophilic organoselenium species, generated <i>in situ</i> through the oxidative cleavage of the Se-Se bond of dibutyl diselenide using Oxone<sup>®</sup> as a green oxidant. The selective formation of the title products was achieved by controlling the solvent identity and the amount of dibutyl diselenide. By using 4.0 equiv of dibutyl diselenide and acetonitrile as solvent at 80 °C, four examples of 3,4-bis(butylselanyl)selenophenes were obtained in moderate to good yields (40–78%). When 3.0 equiv of dibutyl diselenide were used, in the presence of aliphatic alcohols as solvent/nucleophiles under reflux, 10 3-(butylselanyl)-4-alkoxyselenophenes were selectively obtained in low to good yields (15–80%).https://www.mdpi.com/1420-3049/26/8/23781,3-diyneselectrophilic cyclizationheterocycleorganoseleniumselenophene |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Paola S. Hellwig Jonatan S. Guedes Angelita M. Barcellos Gelson Perin Eder J. Lenardão |
spellingShingle |
Paola S. Hellwig Jonatan S. Guedes Angelita M. Barcellos Gelson Perin Eder J. Lenardão Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by Oxone<sup>®</sup> Molecules 1,3-diynes electrophilic cyclization heterocycle organoselenium selenophene |
author_facet |
Paola S. Hellwig Jonatan S. Guedes Angelita M. Barcellos Gelson Perin Eder J. Lenardão |
author_sort |
Paola S. Hellwig |
title |
Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by Oxone<sup>®</sup> |
title_short |
Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by Oxone<sup>®</sup> |
title_full |
Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by Oxone<sup>®</sup> |
title_fullStr |
Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by Oxone<sup>®</sup> |
title_full_unstemmed |
Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by Oxone<sup>®</sup> |
title_sort |
synthesis of 3,4-bis(butylselanyl)selenophenes and 4-alkoxyselenophenes promoted by oxone<sup>®</sup> |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2021-04-01 |
description |
We describe herein an alternative transition-metal-free procedure to access 3,4-bis(butylselanyl)selenophenes and the so far unprecedented 3-(butylselanyl)-4-alkoxyselenophenes. The protocol involves the 5-<i>endo</i>-dig electrophilic cyclization of 1,3-diynes promoted by electrophilic organoselenium species, generated <i>in situ</i> through the oxidative cleavage of the Se-Se bond of dibutyl diselenide using Oxone<sup>®</sup> as a green oxidant. The selective formation of the title products was achieved by controlling the solvent identity and the amount of dibutyl diselenide. By using 4.0 equiv of dibutyl diselenide and acetonitrile as solvent at 80 °C, four examples of 3,4-bis(butylselanyl)selenophenes were obtained in moderate to good yields (40–78%). When 3.0 equiv of dibutyl diselenide were used, in the presence of aliphatic alcohols as solvent/nucleophiles under reflux, 10 3-(butylselanyl)-4-alkoxyselenophenes were selectively obtained in low to good yields (15–80%). |
topic |
1,3-diynes electrophilic cyclization heterocycle organoselenium selenophene |
url |
https://www.mdpi.com/1420-3049/26/8/2378 |
work_keys_str_mv |
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1721518830948188160 |