Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene

The electrochemical reduction of 2-(2,2-dibromovinyl)naphthalene in a DMF solution (Pt cathode) yields selectively 2-ethynylnaphthalene or 2-(bromoethynyl)naphthalene in high yields, depending on the electrolysis conditions. In particular, by simply changing the working potential and the supporting...

Descripción completa

Detalles Bibliográficos
Autores principales: Pandolfi, Fabiana, Chiarotto, Isabella, Feroci, Marta
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5942384/
https://www.ncbi.nlm.nih.gov/pubmed/29765470
http://dx.doi.org/10.3762/bjoc.14.76
_version_ 1783321459297353728
author Pandolfi, Fabiana
Chiarotto, Isabella
Feroci, Marta
author_facet Pandolfi, Fabiana
Chiarotto, Isabella
Feroci, Marta
author_sort Pandolfi, Fabiana
collection PubMed
description The electrochemical reduction of 2-(2,2-dibromovinyl)naphthalene in a DMF solution (Pt cathode) yields selectively 2-ethynylnaphthalene or 2-(bromoethynyl)naphthalene in high yields, depending on the electrolysis conditions. In particular, by simply changing the working potential and the supporting electrolyte, the reaction can be directed towards the synthesis of the terminal alkyne (Et(4)NBF(4)) or the bromoalkyne (NaClO(4)). This study allowed to establish that 2-(bromoethynyl)naphthalene can be converted into 2-ethynylnaphthalene by cathodic reduction.
format Online
Article
Text
id pubmed-5942384
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-59423842018-05-15 Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene Pandolfi, Fabiana Chiarotto, Isabella Feroci, Marta Beilstein J Org Chem Full Research Paper The electrochemical reduction of 2-(2,2-dibromovinyl)naphthalene in a DMF solution (Pt cathode) yields selectively 2-ethynylnaphthalene or 2-(bromoethynyl)naphthalene in high yields, depending on the electrolysis conditions. In particular, by simply changing the working potential and the supporting electrolyte, the reaction can be directed towards the synthesis of the terminal alkyne (Et(4)NBF(4)) or the bromoalkyne (NaClO(4)). This study allowed to establish that 2-(bromoethynyl)naphthalene can be converted into 2-ethynylnaphthalene by cathodic reduction. Beilstein-Institut 2018-04-23 /pmc/articles/PMC5942384/ /pubmed/29765470 http://dx.doi.org/10.3762/bjoc.14.76 Text en Copyright © 2018, Pandolfi et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Pandolfi, Fabiana
Chiarotto, Isabella
Feroci, Marta
Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene
title Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene
title_full Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene
title_fullStr Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene
title_full_unstemmed Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene
title_short Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene
title_sort electrochemically modified corey–fuchs reaction for the synthesis of arylalkynes. the case of 2-(2,2-dibromovinyl)naphthalene
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5942384/
https://www.ncbi.nlm.nih.gov/pubmed/29765470
http://dx.doi.org/10.3762/bjoc.14.76
work_keys_str_mv AT pandolfifabiana electrochemicallymodifiedcoreyfuchsreactionforthesynthesisofarylalkynesthecaseof222dibromovinylnaphthalene
AT chiarottoisabella electrochemicallymodifiedcoreyfuchsreactionforthesynthesisofarylalkynesthecaseof222dibromovinylnaphthalene
AT ferocimarta electrochemicallymodifiedcoreyfuchsreactionforthesynthesisofarylalkynesthecaseof222dibromovinylnaphthalene

Ejemplares similares