Synthesis and structural characterization of ferrocene phosphines modified with polar pendants and their palladium(II) complexes. Part I: N-aminocarbonyl and N-acyl phosphinoferrocene carboxamides

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10331107" target="_blank" >RIV/00216208:11310/16:10331107 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.jorganchem.2016.02.036" target="_blank" >http://dx.doi.org/10.1016/j.jorganchem.2016.02.036</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.jorganchem.2016.02.036" target="_blank" >10.1016/j.jorganchem.2016.02.036</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and structural characterization of ferrocene phosphines modified with polar pendants and their palladium(II) complexes. Part I: N-aminocarbonyl and N-acyl phosphinoferrocene carboxamides

Popis výsledku v původním jazyce

Acylation of 1'-(diphenylphosphino)-1-(aminocarbonyl)ferrocene, Ph(2)PfcCONH(2) (1; fc = ferrocene-1,1'-diyl), afforded a series of acyl-ureas including Ph(2)PfcCONHCONHEt (1a), Ph(2)PfcCONHCONHPh (1b), and Ph(2)PfcCONHCONMe(2) (1c) as well as the acetyl derivative Ph(2)PfcCONHAc (1d). Compounds 1a-d were converted to the corresponding phosphine oxides (2a-d) and further examined as ligands in Pd(II) complexes. The reactions of 1a-d with PdCl2(cod)] (cod = cycloocta-1,5-diene) at a 2:1 ligand-to-metal ratio gave the bis(phosphine) complexes [PdCl2(L-kappa P)(2)] (3a-d; L = 1a-d), whereas the reactions with [Pd(L-NC)Cl](2) (L-NC = [2-(dimethylamino-kappa N)methyl]phenyl-kappa C-1) produced the bridge-cleavage products, [PdCl(L-NC)(L-kappa P)] (4a-d). Removal of the Pd-bound halide from 4a-d with Ag[SbF6] furnished the corresponding cationic bis-chelate complexes [Pd(L-NC)(L-kappa O-2,P)][SbF6] (5a-d). All compounds were characterized by NMR and IR spectroscopy, electrospray ionization mass spectrometry, and elemental analysis. The crystal structures of la, 2a-c, 3a.2CHCl(3), 3b.2CHCl(3), 3d.2CHCl(3), 4a-3CHCl(3), 4b.2.5CHCl(3), 5a.CHCl3, 5b.2CH2Cl(2), and 5d were determined by single-crystal X-ray diffraction analysis, which revealed that the hydrogen-bonded arrays formed in the crystals of free ligands are often preserved in the structures of their complexes.

Název v anglickém jazyce

Synthesis and structural characterization of ferrocene phosphines modified with polar pendants and their palladium(II) complexes. Part I: N-aminocarbonyl and N-acyl phosphinoferrocene carboxamides

Popis výsledku anglicky

Acylation of 1'-(diphenylphosphino)-1-(aminocarbonyl)ferrocene, Ph(2)PfcCONH(2) (1; fc = ferrocene-1,1'-diyl), afforded a series of acyl-ureas including Ph(2)PfcCONHCONHEt (1a), Ph(2)PfcCONHCONHPh (1b), and Ph(2)PfcCONHCONMe(2) (1c) as well as the acetyl derivative Ph(2)PfcCONHAc (1d). Compounds 1a-d were converted to the corresponding phosphine oxides (2a-d) and further examined as ligands in Pd(II) complexes. The reactions of 1a-d with PdCl2(cod)] (cod = cycloocta-1,5-diene) at a 2:1 ligand-to-metal ratio gave the bis(phosphine) complexes [PdCl2(L-kappa P)(2)] (3a-d; L = 1a-d), whereas the reactions with [Pd(L-NC)Cl](2) (L-NC = [2-(dimethylamino-kappa N)methyl]phenyl-kappa C-1) produced the bridge-cleavage products, [PdCl(L-NC)(L-kappa P)] (4a-d). Removal of the Pd-bound halide from 4a-d with Ag[SbF6] furnished the corresponding cationic bis-chelate complexes [Pd(L-NC)(L-kappa O-2,P)][SbF6] (5a-d). All compounds were characterized by NMR and IR spectroscopy, electrospray ionization mass spectrometry, and elemental analysis. The crystal structures of la, 2a-c, 3a.2CHCl(3), 3b.2CHCl(3), 3d.2CHCl(3), 4a-3CHCl(3), 4b.2.5CHCl(3), 5a.CHCl3, 5b.2CH2Cl(2), and 5d were determined by single-crystal X-ray diffraction analysis, which revealed that the hydrogen-bonded arrays formed in the crystals of free ligands are often preserved in the structures of their complexes.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CA - Anorganická chemie

OECD FORD obor

—

Projekt

<a href="/cs/project/GA13-08890S" target="_blank" >GA13-08890S: Polární ferrocenové amidofosfinové ligandy pro katalytické aplikace</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Organometallic Chemistry

ISSN

0022-328X

e-ISSN

—

Svazek periodika

821

Číslo periodika v rámci svazku

October

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

15

Strana od-do

25-39

Kód UT WoS článku

000387633400004

EID výsledku v databázi Scopus

2-s2.0-84960153523