Cargando…

Facile Electrochemical Intramolecular Amination of Urea‐Tethered Terminal Alkenes for the Synthesis of Cyclic Ureas

Facile intramolecular amination of unactivated alkenes has been achieved by using electricity as a catalyst that helps to generate an intermediate and accelerates formation of cyclic ureas in high yields. Using this method, no metal catalysts were used. During electrolysis, a nitrogen radical was fo...

Descripción completa

Detalles Bibliográficos
Autores principales: Ahmed, Nisar, Khatoon, Saira
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6070678/
https://www.ncbi.nlm.nih.gov/pubmed/30083492
http://dx.doi.org/10.1002/open.201800064
_version_ 1783343716435492864
author Ahmed, Nisar
Khatoon, Saira
author_facet Ahmed, Nisar
Khatoon, Saira
author_sort Ahmed, Nisar
collection PubMed
description Facile intramolecular amination of unactivated alkenes has been achieved by using electricity as a catalyst that helps to generate an intermediate and accelerates formation of cyclic ureas in high yields. Using this method, no metal catalysts were used. During electrolysis, a nitrogen radical was formed at the urea substrate that cyclised with the alkene and generated a terminal carbon radical which further formed a bond with the 2,2,6,6‐tetramethylpiperidine‐N‐oxyl radical (TEMPO). This method of electrolysis not only gives cyclic ureas but also functionalises terminal unactivated alkenes. This method can be considered to be environmentally friendly given that it avoids the issues of toxicity or complicated metal ligands and could therefore be potentially employed in green chemistry.
format Online
Article
Text
id pubmed-6070678
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-60706782018-08-06 Facile Electrochemical Intramolecular Amination of Urea‐Tethered Terminal Alkenes for the Synthesis of Cyclic Ureas Ahmed, Nisar Khatoon, Saira ChemistryOpen Full Papers Facile intramolecular amination of unactivated alkenes has been achieved by using electricity as a catalyst that helps to generate an intermediate and accelerates formation of cyclic ureas in high yields. Using this method, no metal catalysts were used. During electrolysis, a nitrogen radical was formed at the urea substrate that cyclised with the alkene and generated a terminal carbon radical which further formed a bond with the 2,2,6,6‐tetramethylpiperidine‐N‐oxyl radical (TEMPO). This method of electrolysis not only gives cyclic ureas but also functionalises terminal unactivated alkenes. This method can be considered to be environmentally friendly given that it avoids the issues of toxicity or complicated metal ligands and could therefore be potentially employed in green chemistry. John Wiley and Sons Inc. 2018-07-09 /pmc/articles/PMC6070678/ /pubmed/30083492 http://dx.doi.org/10.1002/open.201800064 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Full Papers
Ahmed, Nisar
Khatoon, Saira
Facile Electrochemical Intramolecular Amination of Urea‐Tethered Terminal Alkenes for the Synthesis of Cyclic Ureas
title Facile Electrochemical Intramolecular Amination of Urea‐Tethered Terminal Alkenes for the Synthesis of Cyclic Ureas
title_full Facile Electrochemical Intramolecular Amination of Urea‐Tethered Terminal Alkenes for the Synthesis of Cyclic Ureas
title_fullStr Facile Electrochemical Intramolecular Amination of Urea‐Tethered Terminal Alkenes for the Synthesis of Cyclic Ureas
title_full_unstemmed Facile Electrochemical Intramolecular Amination of Urea‐Tethered Terminal Alkenes for the Synthesis of Cyclic Ureas
title_short Facile Electrochemical Intramolecular Amination of Urea‐Tethered Terminal Alkenes for the Synthesis of Cyclic Ureas
title_sort facile electrochemical intramolecular amination of urea‐tethered terminal alkenes for the synthesis of cyclic ureas
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6070678/
https://www.ncbi.nlm.nih.gov/pubmed/30083492
http://dx.doi.org/10.1002/open.201800064
work_keys_str_mv AT ahmednisar facileelectrochemicalintramolecularaminationofureatetheredterminalalkenesforthesynthesisofcyclicureas
AT khatoonsaira facileelectrochemicalintramolecularaminationofureatetheredterminalalkenesforthesynthesisofcyclicureas