Long-range Pd-catalysed C-H functionalization of amine and amino acid derivatives directed by the 2-pyrdylsulfonyl group

Tesis doctoral inédita leída en la Universidad Autónoma de Madrid, Facultad de Ciencias, Departamento de Química Orgánica. Fecha de lectura: 06-10-2021

Detalles Bibliográficos
Autor: Martínez Mingo, Mario
Tipo de recurso: tesis doctoral
Fecha de publicación:2021
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/700181
Acceso en línea:http://hdl.handle.net/10486/700181
Access Level:acceso abierto
Palabra clave:Aminoácidos
Enlace carbono-hidrógeno
Química
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spelling Long-range Pd-catalysed C-H functionalization of amine and amino acid derivatives directed by the 2-pyrdylsulfonyl groupFuncionalización de enlaces C-H a largo alcance catalizado por Pd en derivados de amina y aminoácido dirigido por el grupo 2-piridilsulfoniloMartínez Mingo, MarioAminoácidosEnlace carbono-hidrógenoQuímicaTesis doctoral inédita leída en la Universidad Autónoma de Madrid, Facultad de Ciencias, Departamento de Química Orgánica. Fecha de lectura: 06-10-2021Amines and amino acids are common structural motifs present in a wide number of natural products, biologically active molecules, and highly valuable organic materials. Over the last years, the transition metal-catalyzed functionalization of C–H bonds has emerged as one of the most direct strategies for the post-synthetic modification of this organic features. This dissertation outlines our efforts in the development of novel C–H bond functionalization processes that allow the derivatization of amine derivatives in further positions. For that purpose, we have explored the potential of the 2-pyridylsulfonyl (NSO2Py) group as directing group in long-range Pd-catalyzed C–H functionalization processes, achieving high levels of regio- and chemoselectivity. In particular, we have achieved: - The construction of seven-membered heterocycles, concretely benzazepinone derivatives, through a carbonylative cyclization strategy in ��-position of γ-arylpropyl amine derivatives. - A switchable site-selective methodology in the carbonylative cyclization reaction of γ- aryl-valine type derivatives to obtain benzazepinone or γ-lactam derivatives, through a combination of DFT and experimental mechanistical studies. - The direct introduction of an (hetero)aryl ring in the δ-position of alkyl amine and amino acid derivatives, independently of the substitution pattern along the side-chain. - The selective δ-acetoxylation of alkyl amine derivatives employing PhI(OAc)2 as both oxidant and acetate sourceThis work was supported by the Spanish Ministerio de Economía y Competitividad (MINECO, Grant CTQ2015-66954-P, MINECO/FEDER, UE) and the Spanish Ministerio de Ciencia Innovación y Universidades/FEDER (Agencia Estatal de Investigación/Project PGC2018-098660-B-I00). I also thank MINECO for a FPI predoctoral fellowship (2016- 2021)Carretero Gonzálvez, Juan CarlosRodríguez Garrido, NuriaDepartamento de Química OrgánicaFacultad de Ciencias20212021-10-06doctoral thesishttp://purl.org/coar/resource_type/c_db06NAhttp://purl.org/coar/version/c_be7fb7dd8ff6fe43info:eu-repo/semantics/doctoralThesisapplication/pdfhttp://hdl.handle.net/10486/700181reponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:repositorio.uam.es:10486/7001812026-06-23T12:46:27Z
dc.title.none.fl_str_mv Long-range Pd-catalysed C-H functionalization of amine and amino acid derivatives directed by the 2-pyrdylsulfonyl group
Funcionalización de enlaces C-H a largo alcance catalizado por Pd en derivados de amina y aminoácido dirigido por el grupo 2-piridilsulfonilo
title Long-range Pd-catalysed C-H functionalization of amine and amino acid derivatives directed by the 2-pyrdylsulfonyl group
spellingShingle Long-range Pd-catalysed C-H functionalization of amine and amino acid derivatives directed by the 2-pyrdylsulfonyl group
Martínez Mingo, Mario
Aminoácidos
Enlace carbono-hidrógeno
Química
title_short Long-range Pd-catalysed C-H functionalization of amine and amino acid derivatives directed by the 2-pyrdylsulfonyl group
title_full Long-range Pd-catalysed C-H functionalization of amine and amino acid derivatives directed by the 2-pyrdylsulfonyl group
title_fullStr Long-range Pd-catalysed C-H functionalization of amine and amino acid derivatives directed by the 2-pyrdylsulfonyl group
title_full_unstemmed Long-range Pd-catalysed C-H functionalization of amine and amino acid derivatives directed by the 2-pyrdylsulfonyl group
title_sort Long-range Pd-catalysed C-H functionalization of amine and amino acid derivatives directed by the 2-pyrdylsulfonyl group
dc.creator.none.fl_str_mv Martínez Mingo, Mario
author Martínez Mingo, Mario
author_facet Martínez Mingo, Mario
author_role author
dc.contributor.none.fl_str_mv Carretero Gonzálvez, Juan Carlos
Rodríguez Garrido, Nuria
Departamento de Química Orgánica
Facultad de Ciencias
dc.subject.none.fl_str_mv Aminoácidos
Enlace carbono-hidrógeno
Química
topic Aminoácidos
Enlace carbono-hidrógeno
Química
description Tesis doctoral inédita leída en la Universidad Autónoma de Madrid, Facultad de Ciencias, Departamento de Química Orgánica. Fecha de lectura: 06-10-2021
publishDate 2021
dc.date.none.fl_str_mv 2021
2021-10-06
dc.type.none.fl_str_mv doctoral thesis
http://purl.org/coar/resource_type/c_db06
NA
http://purl.org/coar/version/c_be7fb7dd8ff6fe43
dc.type.openaire.fl_str_mv info:eu-repo/semantics/doctoralThesis
format doctoralThesis
dc.identifier.none.fl_str_mv http://hdl.handle.net/10486/700181
url http://hdl.handle.net/10486/700181
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Biblos-e Archivo. Repositorio Institucional de la UAM
instname:Universidad Autónoma de Madrid
instname_str Universidad Autónoma de Madrid
reponame_str Biblos-e Archivo. Repositorio Institucional de la UAM
collection Biblos-e Archivo. Repositorio Institucional de la UAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300719

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