Specialized Olefin Metathesis Catalysts Featuring Unsymmetrical <i>N</i>-Heterocyclic Carbene Ligands Bearing <i>N</i>-(Fluoren-9-yl) Arm

Specialized Olefin Metathesis Catalysts Featuring Unsymmetrical <i>N</i>-Heterocyclic Carbene Ligands Bearing <i>N</i>-(Fluoren-9-yl) Arm

Beneficial structural motifs from two known state-of-the-art olefin metathesis catalysts types, bearing unsymmetrical <i>N</i>-heterocyclic carbenes (uNHCs), were combined into a new hybridized design thereby translating the complementary beneficial reactivity demonstrated by their ‘pare...

Full description

Bibliographic Details
Main Authors: Phillip I. Jolly, Anna Marczyk, Paweł Małecki, Damian Trzybiński, Krzysztof Woźniak, Anna Kajetanowicz, Karol Grela
Format: Article
Language:English
Published: MDPI AG 2020-05-01
Series:Catalysts
Subjects:
homogeneous catalysis
olefin metathesis
ruthenium
<i>N</i>-heterocyclic carbenes
selectivity
ethenolysis
Online Access:https://www.mdpi.com/2073-4344/10/6/599
id doaj-442d621c3ec14dd08e3ded50580894c5
record_format Article
spelling doaj-442d621c3ec14dd08e3ded50580894c52020-11-25T03:36:43ZengMDPI AGCatalysts2073-43442020-05-011059959910.3390/catal10060599Specialized Olefin Metathesis Catalysts Featuring Unsymmetrical <i>N</i>-Heterocyclic Carbene Ligands Bearing <i>N</i>-(Fluoren-9-yl) ArmPhillip I. Jolly0Anna Marczyk1Paweł Małecki2Damian Trzybiński3Krzysztof Woźniak4Anna Kajetanowicz5Karol Grela6Biological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury Street 101, 02-089 Warsaw, PolandBiological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury Street 101, 02-089 Warsaw, PolandBiological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury Street 101, 02-089 Warsaw, PolandBiological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury Street 101, 02-089 Warsaw, PolandBiological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury Street 101, 02-089 Warsaw, PolandBiological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury Street 101, 02-089 Warsaw, PolandBiological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury Street 101, 02-089 Warsaw, PolandBeneficial structural motifs from two known state-of-the-art olefin metathesis catalysts types, bearing unsymmetrical <i>N</i>-heterocyclic carbenes (uNHCs), were combined into a new hybridized design thereby translating the complementary beneficial reactivity demonstrated by their ‘parent’ complexes to the new <i>N</i>-fluorene derived olefin metathesis catalysts. Two chelating 2-iso-propoxy-benzylidene (Hoveyda-type) and two 3-phenyl-1<i>H</i>-inden-1-ylidene (indenylidene-type) complexes were successfully prepared by in situ generation of either the <i>N′</i>-mesityl (Mes) or <i>N′</i>-diisopropylphenyl (Dipp) derived uNHCs taking advantage of the thermal decomposition of the corresponding 2-(penta-fluorophenyl)-imidazolidines (NHC adducts). The new fluorene-derived catalysts mediate challenging olefin metathesis processes, such as α-olefin self-metathesis, with high selectivity and conversion.https://www.mdpi.com/2073-4344/10/6/599homogeneous catalysisolefin metathesisruthenium<i>N</i>-heterocyclic carbenesselectivityethenolysis
collection DOAJ
language English
format Article
sources DOAJ
author Phillip I. Jolly
Anna Marczyk
Paweł Małecki
Damian Trzybiński
Krzysztof Woźniak
Anna Kajetanowicz
Karol Grela
spellingShingle Phillip I. Jolly
Anna Marczyk
Paweł Małecki
Damian Trzybiński
Krzysztof Woźniak
Anna Kajetanowicz
Karol Grela
Specialized Olefin Metathesis Catalysts Featuring Unsymmetrical <i>N</i>-Heterocyclic Carbene Ligands Bearing <i>N</i>-(Fluoren-9-yl) Arm
Catalysts
homogeneous catalysis
olefin metathesis
ruthenium
<i>N</i>-heterocyclic carbenes
selectivity
ethenolysis
author_facet Phillip I. Jolly
Anna Marczyk
Paweł Małecki
Damian Trzybiński
Krzysztof Woźniak
Anna Kajetanowicz
Karol Grela
author_sort Phillip I. Jolly
title Specialized Olefin Metathesis Catalysts Featuring Unsymmetrical <i>N</i>-Heterocyclic Carbene Ligands Bearing <i>N</i>-(Fluoren-9-yl) Arm
title_short Specialized Olefin Metathesis Catalysts Featuring Unsymmetrical <i>N</i>-Heterocyclic Carbene Ligands Bearing <i>N</i>-(Fluoren-9-yl) Arm
title_full Specialized Olefin Metathesis Catalysts Featuring Unsymmetrical <i>N</i>-Heterocyclic Carbene Ligands Bearing <i>N</i>-(Fluoren-9-yl) Arm
title_fullStr Specialized Olefin Metathesis Catalysts Featuring Unsymmetrical <i>N</i>-Heterocyclic Carbene Ligands Bearing <i>N</i>-(Fluoren-9-yl) Arm
title_full_unstemmed Specialized Olefin Metathesis Catalysts Featuring Unsymmetrical <i>N</i>-Heterocyclic Carbene Ligands Bearing <i>N</i>-(Fluoren-9-yl) Arm
title_sort specialized olefin metathesis catalysts featuring unsymmetrical <i>n</i>-heterocyclic carbene ligands bearing <i>n</i>-(fluoren-9-yl) arm
publisher MDPI AG
series Catalysts
issn 2073-4344
publishDate 2020-05-01
description Beneficial structural motifs from two known state-of-the-art olefin metathesis catalysts types, bearing unsymmetrical <i>N</i>-heterocyclic carbenes (uNHCs), were combined into a new hybridized design thereby translating the complementary beneficial reactivity demonstrated by their ‘parent’ complexes to the new <i>N</i>-fluorene derived olefin metathesis catalysts. Two chelating 2-iso-propoxy-benzylidene (Hoveyda-type) and two 3-phenyl-1<i>H</i>-inden-1-ylidene (indenylidene-type) complexes were successfully prepared by in situ generation of either the <i>N′</i>-mesityl (Mes) or <i>N′</i>-diisopropylphenyl (Dipp) derived uNHCs taking advantage of the thermal decomposition of the corresponding 2-(penta-fluorophenyl)-imidazolidines (NHC adducts). The new fluorene-derived catalysts mediate challenging olefin metathesis processes, such as α-olefin self-metathesis, with high selectivity and conversion.
topic homogeneous catalysis
olefin metathesis
ruthenium
<i>N</i>-heterocyclic carbenes
selectivity
ethenolysis
url https://www.mdpi.com/2073-4344/10/6/599
work_keys_str_mv AT phillipijolly specializedolefinmetathesiscatalystsfeaturingunsymmetricaliniheterocycliccarbeneligandsbearinginifluoren9ylarm
AT annamarczyk specializedolefinmetathesiscatalystsfeaturingunsymmetricaliniheterocycliccarbeneligandsbearinginifluoren9ylarm
AT pawełmałecki specializedolefinmetathesiscatalystsfeaturingunsymmetricaliniheterocycliccarbeneligandsbearinginifluoren9ylarm
AT damiantrzybinski specializedolefinmetathesiscatalystsfeaturingunsymmetricaliniheterocycliccarbeneligandsbearinginifluoren9ylarm
AT krzysztofwozniak specializedolefinmetathesiscatalystsfeaturingunsymmetricaliniheterocycliccarbeneligandsbearinginifluoren9ylarm
AT annakajetanowicz specializedolefinmetathesiscatalystsfeaturingunsymmetricaliniheterocycliccarbeneligandsbearinginifluoren9ylarm
AT karolgrela specializedolefinmetathesiscatalystsfeaturingunsymmetricaliniheterocycliccarbeneligandsbearinginifluoren9ylarm
_version_ 1724548472122638336

Similar Items