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LUND UNIVERSITY LIBRARIES

Synthesis of novel Fe(II)-complexes and study on their catalytic properties in asymmetric epoxidation

Sun, Mingzhe (2014) KEMR12 20132
Department of Chemistry
Abstract
Two novel tetradentate ligands N, N’-Dimethyl-N, N’-bis(2-(chloromethyl)-1-methylbenzimidazole)-
ethane-1,2-diamine (mepL), (-)-2-(((S)-2-((S)-1-(benzimidazol-2-ylmethyl)
pyrrolidin-2-yl) pyrrolidin-1-yl)methyl)benzimidazole (PDPL) and their iron complexes
[Fe(mepL)(CH3CN)2](SbF6)2 (SbF62), [Fe(CF3SO3)2(PDPL)] (OTf1) and [Fe(PDPL)
(CH3CN)2](SbF6)2 (SbF61) were synthesized and characterized with IR, UV-VIS, 1H
NMR and ESI. X-ray crystallographic analysis was performed on OTf1. The complexes’
catalytic capabilities in asymmetric epoxidation reactions were studied using mainly
cyclohexenone as substrate. The influence of several factors on the results have been
investigated, such as carboxylic acid type and loading, catalyst loading,... (More)
Two novel tetradentate ligands N, N’-Dimethyl-N, N’-bis(2-(chloromethyl)-1-methylbenzimidazole)-
ethane-1,2-diamine (mepL), (-)-2-(((S)-2-((S)-1-(benzimidazol-2-ylmethyl)
pyrrolidin-2-yl) pyrrolidin-1-yl)methyl)benzimidazole (PDPL) and their iron complexes
[Fe(mepL)(CH3CN)2](SbF6)2 (SbF62), [Fe(CF3SO3)2(PDPL)] (OTf1) and [Fe(PDPL)
(CH3CN)2](SbF6)2 (SbF61) were synthesized and characterized with IR, UV-VIS, 1H
NMR and ESI. X-ray crystallographic analysis was performed on OTf1. The complexes’
catalytic capabilities in asymmetric epoxidation reactions were studied using mainly
cyclohexenone as substrate. The influence of several factors on the results have been
investigated, such as carboxylic acid type and loading, catalyst loading, reaction
temperature, oxidant loading and different methods of addition of the catalyst. (Less)
Popular Abstract
This thesis is concerned with the preparation of novel iron complexes of new
tetradentate N4 iron complexes and tests of their catalytic capabilities in asymmetric
epoxidation.
Catalytic oxidation of C-H bonds are among the most important reactions in the
chemical industry. Development of effective catalyst for asymmetric oxidation of C-H
bonds and asymmetric epoxidation of olefins are some of the hottest topics in this
field. In recent years, several tetradentate ligand systems have been developed and
their iron complexes have been proven to be capable of providing high yields,
conversions and selectivities in catalytic asymmetric oxidation of various substrates.
It has recently been discovered that high valent ferryl (Fe(IV)=O)... (More)
This thesis is concerned with the preparation of novel iron complexes of new
tetradentate N4 iron complexes and tests of their catalytic capabilities in asymmetric
epoxidation.
Catalytic oxidation of C-H bonds are among the most important reactions in the
chemical industry. Development of effective catalyst for asymmetric oxidation of C-H
bonds and asymmetric epoxidation of olefins are some of the hottest topics in this
field. In recent years, several tetradentate ligand systems have been developed and
their iron complexes have been proven to be capable of providing high yields,
conversions and selectivities in catalytic asymmetric oxidation of various substrates.
It has recently been discovered that high valent ferryl (Fe(IV)=O) or perferryl
(Fe(V)=O) species are generated during the oxidation process and are the direct
oxidants of the carbon hydrogen bonds. In the successful catalysts developed so far,
the basic idea is the utilization of the ligand to alleviate the positive charge from the
metal centre during the intermediate stage, which leads to better stabilization of the
high valent ferryl species. This gave the inspiration for the design of the two
tetradentate N4 ligand systems in this work and the catalytic properties of their FeII
complexes were examined in the asymmetric epoxidation of cycloalkenone which is a
difficult type of substrate to oxidize in a highly selective way. (Less)
Please use this url to cite or link to this publication:
author
Sun, Mingzhe
supervisor
organization
course
KEMR12 20132
year
type
H2 - Master's Degree (Two Years)
subject
keywords
oorganisk kemi, inorganic chemistry
language
English
id
4646165
date added to LUP
2014-09-12 16:19:38
date last changed
2014-09-12 16:19:38
@misc{4646165,
  abstract     = {{Two novel tetradentate ligands N, N’-Dimethyl-N, N’-bis(2-(chloromethyl)-1-methylbenzimidazole)-
ethane-1,2-diamine (mepL), (-)-2-(((S)-2-((S)-1-(benzimidazol-2-ylmethyl)
pyrrolidin-2-yl) pyrrolidin-1-yl)methyl)benzimidazole (PDPL) and their iron complexes
[Fe(mepL)(CH3CN)2](SbF6)2 (SbF62), [Fe(CF3SO3)2(PDPL)] (OTf1) and [Fe(PDPL)
(CH3CN)2](SbF6)2 (SbF61) were synthesized and characterized with IR, UV-VIS, 1H
NMR and ESI. X-ray crystallographic analysis was performed on OTf1. The complexes’
catalytic capabilities in asymmetric epoxidation reactions were studied using mainly
cyclohexenone as substrate. The influence of several factors on the results have been
investigated, such as carboxylic acid type and loading, catalyst loading, reaction
temperature, oxidant loading and different methods of addition of the catalyst.}},
  author       = {{Sun, Mingzhe}},
  language     = {{eng}},
  note         = {{Student Paper}},
  title        = {{Synthesis of novel Fe(II)-complexes and study on their catalytic properties in asymmetric epoxidation}},
  year         = {{2014}},
}