Oxidation of unactivated C-H bonds catalyzed by manganese complexes: control over site-selectivity and enantioselectivity
The oxidation of aliphatic C-H bonds is a very powerful reaction because it allows the functionalization of inert C-H bonds, converting them into a suitable sites for further chemical elaboration. It also represents one of the most challenging reactions in modern synthetic organic chemistry because...
| Autor: | |
|---|---|
| Tipo de recurso: | tesis doctoral |
| Estado: | Versión publicada |
| Fecha de publicación: | 2018 |
| País: | España |
| Institución: | CBUC, CESCA |
| Repositorio: | TDR. Tesis Doctorales en Red |
| OAI Identifier: | oai:www.tdx.cat:10803/664865 |
| Acceso en línea: | http://hdl.handle.net/10803/664865 |
| Access Level: | acceso abierto |
| Palabra clave: | C-H oxidation Oxidació de CH Oxidación de CH Manganeses complexes Complexos de manganès Complejos de manganeso Bioinspired models Models bioinspirats Modelos bioinspirados Metal catalysts Catalitzadors de metalls Catalizadores de metales 546 |
| id |
ES_cd01262e109aaaa9e1e00fcbf237104d |
|---|---|
| oai_identifier_str |
oai:www.tdx.cat:10803/664865 |
| network_acronym_str |
ES |
| network_name_str |
España |
| repository_id_str |
|
| spelling |
Oxidation of unactivated C-H bonds catalyzed by manganese complexes: control over site-selectivity and enantioselectivityMilan, MichelaC-H oxidationOxidació de CHOxidación de CHManganeses complexesComplexos de manganèsComplejos de manganesoBioinspired modelsModels bioinspiratsModelos bioinspiradosMetal catalystsCatalitzadors de metallsCatalizadores de metales546The oxidation of aliphatic C-H bonds is a very powerful reaction because it allows the functionalization of inert C-H bonds, converting them into a suitable sites for further chemical elaboration. It also represents one of the most challenging reactions in modern synthetic organic chemistry because the multitude of aliphatic C-H bonds in a molecule makes site selective oxidation particularly difficult. Moreover, the introduction of chirality represents an unmet but very appealing challenge, because the asymmetric oxidation of hydrocarbons produces chiral compounds of high value in organic synthesis from readily available starting materials. Until now, examples of enantioselective oxidation of nonactivated aliphatic C-H bonds remain exclusive to enzymes. This thesis has been devoted to the development of new catalytic systems capable to oxidize nonactivated aliphatic C-H bonds in a site-selective and enantioselective manner. In particularly, chemo- and enantioselective aliphatic C-H oxidation reactions, especially focused in amide containing substrates have been developed.L'oxidació d’enllaços C-H alifàtics és una reacció altament interessant perquè permet funcionalitzar l'enllaç C-H inert, generant molècules d’alt interès sintètic. No obstant, també es tracta d'una de les reaccions que més atenció ha generat en en el camp de la química orgànica sintètica moderna perquè la multitud d'enllaços C-H alifàtics present en una mateixa molècula fa que l'oxidació selectiva d’un enllaç específic sigui particularment difícil. A més, la introducció de quiralitat en aquesta reacció representa, encara a dia d’avui, un repte molt atractiu, ja que l'oxidació asimètrica d'hidrocarburs, compostos altament abundants a la naturalesa, permet l'obtenció de compostos quirals d'alt valor en síntesi orgànica; i de moment, segueix sent una transformació exclusiva dels enzims. En particular, s'han desenvolupat reaccions d'oxidació de C-H alifàtiques quimio- i enantioselectives, enfocades en substrats que contenen un grup funcional amida.Universitat de GironaCostas Salgueiro, MiquelBietti, MassimoCostas Salgueiro, MiquelUniversitat de Girona. Departament de Química201920192018info:eu-repo/semantics/doctoralThesisinfo:eu-repo/semantics/publishedVersion340 p.application/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/10803/664865TDX (Tesis Doctorals en Xarxa)reponame:TDR. Tesis Doctorales en Redinstname:CBUC, CESCAInglésL'accés als continguts d'aquesta tesi queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons: http://creativecommons.org/licenses/by/4.0/http://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:www.tdx.cat:10803/6648652026-06-14T12:46:07Z |
| dc.title.none.fl_str_mv |
Oxidation of unactivated C-H bonds catalyzed by manganese complexes: control over site-selectivity and enantioselectivity |
| title |
Oxidation of unactivated C-H bonds catalyzed by manganese complexes: control over site-selectivity and enantioselectivity |
| spellingShingle |
Oxidation of unactivated C-H bonds catalyzed by manganese complexes: control over site-selectivity and enantioselectivity Milan, Michela C-H oxidation Oxidació de CH Oxidación de CH Manganeses complexes Complexos de manganès Complejos de manganeso Bioinspired models Models bioinspirats Modelos bioinspirados Metal catalysts Catalitzadors de metalls Catalizadores de metales 546 |
| title_short |
Oxidation of unactivated C-H bonds catalyzed by manganese complexes: control over site-selectivity and enantioselectivity |
| title_full |
Oxidation of unactivated C-H bonds catalyzed by manganese complexes: control over site-selectivity and enantioselectivity |
| title_fullStr |
Oxidation of unactivated C-H bonds catalyzed by manganese complexes: control over site-selectivity and enantioselectivity |
| title_full_unstemmed |
Oxidation of unactivated C-H bonds catalyzed by manganese complexes: control over site-selectivity and enantioselectivity |
| title_sort |
Oxidation of unactivated C-H bonds catalyzed by manganese complexes: control over site-selectivity and enantioselectivity |
| dc.creator.none.fl_str_mv |
Milan, Michela |
| author |
Milan, Michela |
| author_facet |
Milan, Michela |
| author_role |
author |
| dc.contributor.none.fl_str_mv |
Costas Salgueiro, Miquel Bietti, Massimo Costas Salgueiro, Miquel Universitat de Girona. Departament de Química |
| dc.subject.none.fl_str_mv |
C-H oxidation Oxidació de CH Oxidación de CH Manganeses complexes Complexos de manganès Complejos de manganeso Bioinspired models Models bioinspirats Modelos bioinspirados Metal catalysts Catalitzadors de metalls Catalizadores de metales 546 |
| topic |
C-H oxidation Oxidació de CH Oxidación de CH Manganeses complexes Complexos de manganès Complejos de manganeso Bioinspired models Models bioinspirats Modelos bioinspirados Metal catalysts Catalitzadors de metalls Catalizadores de metales 546 |
| description |
The oxidation of aliphatic C-H bonds is a very powerful reaction because it allows the functionalization of inert C-H bonds, converting them into a suitable sites for further chemical elaboration. It also represents one of the most challenging reactions in modern synthetic organic chemistry because the multitude of aliphatic C-H bonds in a molecule makes site selective oxidation particularly difficult. Moreover, the introduction of chirality represents an unmet but very appealing challenge, because the asymmetric oxidation of hydrocarbons produces chiral compounds of high value in organic synthesis from readily available starting materials. Until now, examples of enantioselective oxidation of nonactivated aliphatic C-H bonds remain exclusive to enzymes. This thesis has been devoted to the development of new catalytic systems capable to oxidize nonactivated aliphatic C-H bonds in a site-selective and enantioselective manner. In particularly, chemo- and enantioselective aliphatic C-H oxidation reactions, especially focused in amide containing substrates have been developed. |
| publishDate |
2018 |
| dc.date.none.fl_str_mv |
2018 2019 2019 |
| dc.type.none.fl_str_mv |
info:eu-repo/semantics/doctoralThesis info:eu-repo/semantics/publishedVersion |
| format |
doctoralThesis |
| status_str |
publishedVersion |
| dc.identifier.none.fl_str_mv |
http://hdl.handle.net/10803/664865 |
| url |
http://hdl.handle.net/10803/664865 |
| dc.language.none.fl_str_mv |
Inglés |
| language_invalid_str_mv |
Inglés |
| dc.rights.none.fl_str_mv |
http://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess |
| rights_invalid_str_mv |
http://creativecommons.org/licenses/by/4.0/ |
| eu_rights_str_mv |
openAccess |
| dc.format.none.fl_str_mv |
340 p. application/pdf application/pdf application/pdf |
| dc.publisher.none.fl_str_mv |
Universitat de Girona |
| publisher.none.fl_str_mv |
Universitat de Girona |
| dc.source.none.fl_str_mv |
TDX (Tesis Doctorals en Xarxa) reponame:TDR. Tesis Doctorales en Red instname:CBUC, CESCA |
| instname_str |
CBUC, CESCA |
| reponame_str |
TDR. Tesis Doctorales en Red |
| collection |
TDR. Tesis Doctorales en Red |
| repository.name.fl_str_mv |
|
| repository.mail.fl_str_mv |
|
| _version_ |
1869419771436466176 |
| score |
15.300719 |