Reactivity toward CO of Eight-Membered Palladacycles Derived from the Insertion of Alkenes into the Pd–C Bond of Cyclopalladated Primary Arylalkylamines of Pharmaceutical Interest. Synthesis of Tetrahydrobenzazocinones, Ortho-Functionalized Phenethylamines, Ureas, and an Isocyanate

García-López, José-Antonio; Oliva-Madrid, María-José; Saura-Llamas, Isabel; Bautista, Delia; Vicente, José

Publication:
Reactivity toward CO of Eight-Membered Palladacycles Derived from the Insertion of Alkenes into the Pd–C Bond of Cyclopalladated Primary Arylalkylamines of Pharmaceutical Interest. Synthesis of Tetrahydrobenzazocinones, Ortho-Functionalized Phenethylamines, Ureas, and an Isocyanate

dc.contributor.advisor	Vicente, José
dc.contributor.author	García-López, José-Antonio
dc.contributor.author	Oliva-Madrid, María-José
dc.contributor.author	Saura-Llamas, Isabel
dc.contributor.author	Bautista, Delia
dc.contributor.author	Vicente, José
dc.contributor.department	Química Inorgánica
dc.date.accessioned	2024-01-17T11:52:43Z
dc.date.available	2024-01-17T11:52:43Z
dc.date.created	2012
dc.date.issued	2012-08-16
dc.description	This document is made available under the CC-BY 4.0 license http://creativecommons.org/licenses/by /4.0/. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organometallics copyright © American Chemical Society, after peer review and technical editing by the publisher.	es
dc.description.abstract	The ortho-metalated complex [Pd{C,N-C6H2CH2CH2NH2-2,(OMe)2-4,5}(μ-Br)]2 (1a) derived from homoveratrylamine reacts with ethyl acrylate, methyl vinyl ketone or 2-norbornene to give the dimeric complex arising from the insertion of the alkene into the Pd–C bond, [Pd{C,N-CH(R)CH2C6H2CH2CH2NH2-2,(OMe)2-4,5}(μ-Br)]2 (R = CO2Et (2a1), C(O)Me (2a2)) or [Pd{C,N-CH(C5H8)CHC6H2CH2CH2NH2-2,(OMe)2-4,5}(μ-Br)]2 (2a3). Complexes 2a and the phentermine homologues 2b react with CO to afford Pd(0) and (1) tetrahydrobenzazocinones, the heterocycles resulting from CO insertion into the Pd–C bond and C–N coupling, (2) unnatural aminoacid derivatives resulting from CO insertion and the reaction of the obtained acyl complex with the solvent (MeOH), or the product of protonolysis of the Pd–C bond, depending on the nature of the initial cyclopalladated compound or (3) ureas, alone or mixed with an isocyanate, in the presence of a base. Phentermine derivatives 2b react with HCl to give a dinuclear palladium complex [PdCl(μ- Cl)(L)], where L is the amine arising from the protonolysis of the Pd–C bond or the alkyl group resulting from Pd–N bond protonolysis, depending on the nature of the inserted alkene. The crystal structures of some palladium complexes and organic compounds have been determined by X-ray diffraction studies.	es
dc.format	application/pdf	es
dc.format.extent	53	es
dc.identifier.citation	Organometallics 2012, 31, 17, 6351–6364
dc.identifier.doi	https://doi.org/10.1021/om300593x
dc.identifier.issn	Print: 0276-7333
dc.identifier.issn	Electronic: 1520-6041
dc.identifier.uri	http://hdl.handle.net/10201/137374
dc.language	eng	es
dc.publisher	ACS	es
dc.relation	Ministerio de Educación y Ciencia, FEDER Convocatoria: 2007 (CTQ2007-60808/BQU, C-Consolider) Fundación Séneca (04539/GERM/06)	es
dc.relation.ispartof	Compuestos organometálicos y de coordinación funcionalizados. Síntesis y reactividad funcionalizados (CTQ2007-60808/BQU, C-Consolider)	es
dc.relation.publisherversion	https://pubs.acs.org/doi/10.1021/om300593x	es
dc.rights	info:eu-repo/semantics/openAccess	es
dc.rights	Atribución 4.0 Internacional	*
dc.rights.uri	http://creativecommons.org/licenses/by/4.0/	*
dc.subject	Paladio	es
dc.subject	Paladaciclo	es
dc.subject	Inserción	es
dc.subject	Láquenos	es
dc.subject.other	CDU::5 - Ciencias puras y naturales	es
dc.subject.other	CDU::5 - Ciencias puras y naturales::54 - Química	es
dc.title	Reactivity toward CO of Eight-Membered Palladacycles Derived from the Insertion of Alkenes into the Pd–C Bond of Cyclopalladated Primary Arylalkylamines of Pharmaceutical Interest. Synthesis of Tetrahydrobenzazocinones, Ortho-Functionalized Phenethylamines, Ureas, and an Isocyanate	es
dc.type	info:eu-repo/semantics/article	es
dspace.entity.type	Publication	es