From recovered metal waste to high-performance palladium catalysts

The catalytic activity of a series of neutral and cationic, homo- and heteroleptic, mono- and bimetallic palladium(ii) compounds based on dithiocarbamate and dithiooxamide S,S-donor ligands is described. High activity was observed in the regio- and chemo-selective C-H functionalization of benzo[h]qu...

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Published in:Green Chemistry
Main Author: Jantan K.A.; Kwok C.Y.; Chan K.W.; Marchiò L.; White A.J.P.; Deplano P.; Serpe A.; Wilton-Ely J.D.E.T.
Format: Article
Language:English
Published: Royal Society of Chemistry 2017
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85038427912&doi=10.1039%2fc7gc02678a&partnerID=40&md5=92a300b4e88bb3273bddafbcfbb6e783
id 2-s2.0-85038427912
spelling 2-s2.0-85038427912
Jantan K.A.; Kwok C.Y.; Chan K.W.; Marchiò L.; White A.J.P.; Deplano P.; Serpe A.; Wilton-Ely J.D.E.T.
From recovered metal waste to high-performance palladium catalysts
2017
Green Chemistry
19
24
10.1039/c7gc02678a
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85038427912&doi=10.1039%2fc7gc02678a&partnerID=40&md5=92a300b4e88bb3273bddafbcfbb6e783
The catalytic activity of a series of neutral and cationic, homo- and heteroleptic, mono- and bimetallic palladium(ii) compounds based on dithiocarbamate and dithiooxamide S,S-donor ligands is described. High activity was observed in the regio- and chemo-selective C-H functionalization of benzo[h]quinoline to 10-alkoxybenzo[h]quinoline and 8-methylquinoline to 8-(methoxymethyl)quinoline in the presence of the oxidant PhI(OAc)2. The best performance was found for [Pd(Me2dazdt)2]I6 (Me2dazdt = N,N′-dimethyl-perhydrodiazepine-2,3-dithione), [PdI2(Me2dazdt)] and [Pd(Cy2DTO)2]I8 (Cy2DTO = N,N′-dicyclohexyl-dithiooxamide) which are all obtained directly as products of sustainable Pd-metal leaching processes used to recover palladium from scrap metal. These compounds provided almost quantitative yields under milder conditions (50 °C, 1-3 mol% Pd loading) and much shorter reaction times (1-3 h) than reported previously. These results illustrate how the complexes obtained from the selective and sustainable recovery of Pd from automotive heterogeneous Three Way Catalysts (TWC) can be employed directly in homogeneous catalysis, avoiding further metal recovery steps and valorising the metal complex itself in a 'circular economy' model. © 2017 The Royal Society of Chemistry.
Royal Society of Chemistry
14639262
English
Article

author Jantan K.A.; Kwok C.Y.; Chan K.W.; Marchiò L.; White A.J.P.; Deplano P.; Serpe A.; Wilton-Ely J.D.E.T.
spellingShingle Jantan K.A.; Kwok C.Y.; Chan K.W.; Marchiò L.; White A.J.P.; Deplano P.; Serpe A.; Wilton-Ely J.D.E.T.
From recovered metal waste to high-performance palladium catalysts
author_facet Jantan K.A.; Kwok C.Y.; Chan K.W.; Marchiò L.; White A.J.P.; Deplano P.; Serpe A.; Wilton-Ely J.D.E.T.
author_sort Jantan K.A.; Kwok C.Y.; Chan K.W.; Marchiò L.; White A.J.P.; Deplano P.; Serpe A.; Wilton-Ely J.D.E.T.
title From recovered metal waste to high-performance palladium catalysts
title_short From recovered metal waste to high-performance palladium catalysts
title_full From recovered metal waste to high-performance palladium catalysts
title_fullStr From recovered metal waste to high-performance palladium catalysts
title_full_unstemmed From recovered metal waste to high-performance palladium catalysts
title_sort From recovered metal waste to high-performance palladium catalysts
publishDate 2017
container_title Green Chemistry
container_volume 19
container_issue 24
doi_str_mv 10.1039/c7gc02678a
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85038427912&doi=10.1039%2fc7gc02678a&partnerID=40&md5=92a300b4e88bb3273bddafbcfbb6e783
description The catalytic activity of a series of neutral and cationic, homo- and heteroleptic, mono- and bimetallic palladium(ii) compounds based on dithiocarbamate and dithiooxamide S,S-donor ligands is described. High activity was observed in the regio- and chemo-selective C-H functionalization of benzo[h]quinoline to 10-alkoxybenzo[h]quinoline and 8-methylquinoline to 8-(methoxymethyl)quinoline in the presence of the oxidant PhI(OAc)2. The best performance was found for [Pd(Me2dazdt)2]I6 (Me2dazdt = N,N′-dimethyl-perhydrodiazepine-2,3-dithione), [PdI2(Me2dazdt)] and [Pd(Cy2DTO)2]I8 (Cy2DTO = N,N′-dicyclohexyl-dithiooxamide) which are all obtained directly as products of sustainable Pd-metal leaching processes used to recover palladium from scrap metal. These compounds provided almost quantitative yields under milder conditions (50 °C, 1-3 mol% Pd loading) and much shorter reaction times (1-3 h) than reported previously. These results illustrate how the complexes obtained from the selective and sustainable recovery of Pd from automotive heterogeneous Three Way Catalysts (TWC) can be employed directly in homogeneous catalysis, avoiding further metal recovery steps and valorising the metal complex itself in a 'circular economy' model. © 2017 The Royal Society of Chemistry.
publisher Royal Society of Chemistry
issn 14639262
language English
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