New palladium (II) complexes containing phosphine-nitrogen ligands and their use as catalysts in aminocarbonylation reaction

Braulio Aranda, Sergio A. Moya, Andres Vega, Gonzalo Valdebenito, Sofia Ramirez-Lopez, Pedro Aguirre

Resultado de la investigación: Article

Resumen

Aminocarbonylation of aryl halides, homogeneously catalysed by palladium, is an efficient method that can be employed for obtaining amides for pharmaceutical and synthetic applications. In this work, palladium (II) complexes containing P^N ligands were studied as catalysts in the aminocarbonylation of iodobenzene in the presence of diethylamine. Two types of systems were used: a palladium (II) complex formed in situ; and one prepared prior to the catalytic reaction. In general, the palladium complexes studied achieved high conversions in an average reaction time of less than 2 hr, which is less than that for the standard system (Pd (II)/PPh 3 ) used. The pre-synthesized complexes were faster than their in situ counterparts, as the latter require an induction time to form the Pd/P^N species. The structure and electronic properties of the ligand P^N can influence both the activity and the selectivity of the reaction, stabilizing the acyl-palladium intermediates formed in a better manner.

Idioma originalEnglish
Número de artículoe4709
PublicaciónApplied Organometallic Chemistry
Volumen33
N.º4
DOI
EstadoPublished - 1 abr 2019

Huella dactilar

phosphine
Palladium
Nitrogen
Ligands
Catalysts
Amides
Electronic properties

ASJC Scopus subject areas

  • Chemistry(all)
  • Inorganic Chemistry

Citar esto

Aranda, Braulio ; Moya, Sergio A. ; Vega, Andres ; Valdebenito, Gonzalo ; Ramirez-Lopez, Sofia ; Aguirre, Pedro. / New palladium (II) complexes containing phosphine-nitrogen ligands and their use as catalysts in aminocarbonylation reaction. En: Applied Organometallic Chemistry. 2019 ; Vol. 33, N.º 4.
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abstract = "Aminocarbonylation of aryl halides, homogeneously catalysed by palladium, is an efficient method that can be employed for obtaining amides for pharmaceutical and synthetic applications. In this work, palladium (II) complexes containing P^N ligands were studied as catalysts in the aminocarbonylation of iodobenzene in the presence of diethylamine. Two types of systems were used: a palladium (II) complex formed in situ; and one prepared prior to the catalytic reaction. In general, the palladium complexes studied achieved high conversions in an average reaction time of less than 2 hr, which is less than that for the standard system (Pd (II)/PPh 3 ) used. The pre-synthesized complexes were faster than their in situ counterparts, as the latter require an induction time to form the Pd/P^N species. The structure and electronic properties of the ligand P^N can influence both the activity and the selectivity of the reaction, stabilizing the acyl-palladium intermediates formed in a better manner.",
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New palladium (II) complexes containing phosphine-nitrogen ligands and their use as catalysts in aminocarbonylation reaction. / Aranda, Braulio; Moya, Sergio A.; Vega, Andres; Valdebenito, Gonzalo; Ramirez-Lopez, Sofia; Aguirre, Pedro.

En: Applied Organometallic Chemistry, Vol. 33, N.º 4, e4709, 01.04.2019.

Resultado de la investigación: Article

TY - JOUR

T1 - New palladium (II) complexes containing phosphine-nitrogen ligands and their use as catalysts in aminocarbonylation reaction

AU - Aranda, Braulio

AU - Moya, Sergio A.

AU - Vega, Andres

AU - Valdebenito, Gonzalo

AU - Ramirez-Lopez, Sofia

AU - Aguirre, Pedro

PY - 2019/4/1

Y1 - 2019/4/1

N2 - Aminocarbonylation of aryl halides, homogeneously catalysed by palladium, is an efficient method that can be employed for obtaining amides for pharmaceutical and synthetic applications. In this work, palladium (II) complexes containing P^N ligands were studied as catalysts in the aminocarbonylation of iodobenzene in the presence of diethylamine. Two types of systems were used: a palladium (II) complex formed in situ; and one prepared prior to the catalytic reaction. In general, the palladium complexes studied achieved high conversions in an average reaction time of less than 2 hr, which is less than that for the standard system (Pd (II)/PPh 3 ) used. The pre-synthesized complexes were faster than their in situ counterparts, as the latter require an induction time to form the Pd/P^N species. The structure and electronic properties of the ligand P^N can influence both the activity and the selectivity of the reaction, stabilizing the acyl-palladium intermediates formed in a better manner.

AB - Aminocarbonylation of aryl halides, homogeneously catalysed by palladium, is an efficient method that can be employed for obtaining amides for pharmaceutical and synthetic applications. In this work, palladium (II) complexes containing P^N ligands were studied as catalysts in the aminocarbonylation of iodobenzene in the presence of diethylamine. Two types of systems were used: a palladium (II) complex formed in situ; and one prepared prior to the catalytic reaction. In general, the palladium complexes studied achieved high conversions in an average reaction time of less than 2 hr, which is less than that for the standard system (Pd (II)/PPh 3 ) used. The pre-synthesized complexes were faster than their in situ counterparts, as the latter require an induction time to form the Pd/P^N species. The structure and electronic properties of the ligand P^N can influence both the activity and the selectivity of the reaction, stabilizing the acyl-palladium intermediates formed in a better manner.

KW - amide synthesis

KW - aminocarbonylation

KW - aryl halide

KW - palladium complex

KW - phospho-nitrogen ligands

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