Copper- and Amine-free Sonogashira Cross-Coupling in the Presence of Ligandless Pd-containing Catalyst

In this work, the effect of reaction conditions (temperature and composition of the reaction mixture) on the Cu-free Sonogashira cross-coupling of 4-iodoanisole (IAn) and phenylacethylene using nanoparticulate ligandless palladium catalyst based on hyper-cross-linked aromatic polymer (HAP) was studi...

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Autores principales:	Linda Zh. Nikoshvili, Elena P. Tupikina, Lioubov Kiwi-Minsker
Formato:	article
Lenguaje:	EN
Publicado:	AIDIC Servizi S.r.l. 2021
Materias:	Chemical engineering TP155-156 Computer engineering. Computer hardware TK7885-7895
Acceso en línea:	https://doaj.org/article/09dd0a8c34094d858ec49da004745db6
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spelling	oai:doaj.org-article:09dd0a8c34094d858ec49da004745db62021-11-15T21:48:41ZCopper- and Amine-free Sonogashira Cross-Coupling in the Presence of Ligandless Pd-containing Catalyst10.3303/CET21880452283-9216https://doaj.org/article/09dd0a8c34094d858ec49da004745db62021-11-01T00:00:00Zhttps://www.cetjournal.it/index.php/cet/article/view/11838https://doaj.org/toc/2283-9216In this work, the effect of reaction conditions (temperature and composition of the reaction mixture) on the Cu-free Sonogashira cross-coupling of 4-iodoanisole (IAn) and phenylacethylene using nanoparticulate ligandless palladium catalyst based on hyper-cross-linked aromatic polymer (HAP) was studied. Main idea of the study is the ability of HAP to stabilize small Pd nanoparticles that allows developing effective catalysts. It was shown that > 99 % conversion of IAn can be achieved in the presence of Pd/HAP for 1 h at 90 ?? at the absence of amines and copper while using DMSO as a medium. DMSO allowed high solubility of all the reaction components and likely played a role of ligand in the Sonogashira reaction cycle. After the reaction, the cross-coupling product (1-methoxy-4-(phenylethynyl)benzene) was purified, its structure was confirmed by NMR.Linda Zh. NikoshviliElena P. TupikinaLioubov Kiwi-MinskerAIDIC Servizi S.r.l.articleChemical engineeringTP155-156Computer engineering. Computer hardwareTK7885-7895ENChemical Engineering Transactions, Vol 88 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Chemical engineering TP155-156 Computer engineering. Computer hardware TK7885-7895
spellingShingle	Chemical engineering TP155-156 Computer engineering. Computer hardware TK7885-7895 Linda Zh. Nikoshvili Elena P. Tupikina Lioubov Kiwi-Minsker Copper- and Amine-free Sonogashira Cross-Coupling in the Presence of Ligandless Pd-containing Catalyst
description	In this work, the effect of reaction conditions (temperature and composition of the reaction mixture) on the Cu-free Sonogashira cross-coupling of 4-iodoanisole (IAn) and phenylacethylene using nanoparticulate ligandless palladium catalyst based on hyper-cross-linked aromatic polymer (HAP) was studied. Main idea of the study is the ability of HAP to stabilize small Pd nanoparticles that allows developing effective catalysts. It was shown that > 99 % conversion of IAn can be achieved in the presence of Pd/HAP for 1 h at 90 ?? at the absence of amines and copper while using DMSO as a medium. DMSO allowed high solubility of all the reaction components and likely played a role of ligand in the Sonogashira reaction cycle. After the reaction, the cross-coupling product (1-methoxy-4-(phenylethynyl)benzene) was purified, its structure was confirmed by NMR.
format	article
author	Linda Zh. Nikoshvili Elena P. Tupikina Lioubov Kiwi-Minsker
author_facet	Linda Zh. Nikoshvili Elena P. Tupikina Lioubov Kiwi-Minsker
author_sort	Linda Zh. Nikoshvili
title	Copper- and Amine-free Sonogashira Cross-Coupling in the Presence of Ligandless Pd-containing Catalyst
title_short	Copper- and Amine-free Sonogashira Cross-Coupling in the Presence of Ligandless Pd-containing Catalyst
title_full	Copper- and Amine-free Sonogashira Cross-Coupling in the Presence of Ligandless Pd-containing Catalyst
title_fullStr	Copper- and Amine-free Sonogashira Cross-Coupling in the Presence of Ligandless Pd-containing Catalyst
title_full_unstemmed	Copper- and Amine-free Sonogashira Cross-Coupling in the Presence of Ligandless Pd-containing Catalyst
title_sort	copper- and amine-free sonogashira cross-coupling in the presence of ligandless pd-containing catalyst
publisher	AIDIC Servizi S.r.l.
publishDate	2021
url	https://doaj.org/article/09dd0a8c34094d858ec49da004745db6
work_keys_str_mv	AT lindazhnikoshvili copperandaminefreesonogashiracrosscouplinginthepresenceofligandlesspdcontainingcatalyst AT elenaptupikina copperandaminefreesonogashiracrosscouplinginthepresenceofligandlesspdcontainingcatalyst AT lioubovkiwiminsker copperandaminefreesonogashiracrosscouplinginthepresenceofligandlesspdcontainingcatalyst
_version_	1718426766750515200

Copper- and Amine-free Sonogashira Cross-Coupling in the Presence of Ligandless Pd-containing Catalyst

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