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Statements

Subject Item
n2:RIV%2F00216208%3A11310%2F12%3A10126165%21RIV13-MSM-11310___
rdf:type
skos:Concept n16:Vysledek
rdfs:seeAlso
http://dx.doi.org/10.1021/om2011529
dcterms:description
The reaction of pentafluorophenyl 1'-(diphenylphosphino)ferrocene-1-carboxylate (4) with omega-aminosulfonic acids H2N(CH2)nSO3H (n = 1-3) in the presence of 4-(dimethylamino)pyridine and triethylamine affords the respective phosphinoferrocene amidosulfonates as crystalline triethylammonium salts, viz., (Et3NH)[Ph2PfcCONH(CH2)nSO3] (1, n = 1; 2, n = 2; 3, n = 3; fc = ferrocene-1,1'-diyl), in good yields. These ligands react smoothly with [PdCl2(cod)] (cod = eta(2):eta(2)-cycloocta-1,5-diene) to give the anionic square-planar bis-phosphine complexes trans-(Et3NH)2[PdCl2(Ph2PfcCONH(CH2)nSO3-kappa P)2] (5, n = 1; 6, n = 2; and 7, n = 3). The chloride-bridged dimer [LPdCl]2, where L is 2-[(dimethylamino-kappa N)methyl]phenyl-kappa C-1 auxiliary ligand, is cleaved with 1 to give (Et3NH)[LPd(Ph2PfcCONHCH2SO(3)-kappa P)] (8), in which the amidosulfonate coordinates as a simple phosphine. A similar reaction of [LPd(OAc)]2 and 1 proceeds under a partial elimination of (Et3NH)OAc to afford a mixture of zwitterionic bis-chelate [LPd(Ph2PfcCONHCH2SO3-kappa O-2,P)] (9) and another Pd(II) complex tentatively formulated as [LPd(OAc)(Ph2PfcCONHCH2SO3-kappa P)] (9a), from which the former complex separates as an analytically pure crystalline solid. All compounds have been characterized by spectroscopic methods and elemental analysis. The crystal structures of 1, 3, 5.2.5CH2Cl2, and 9.2CHCl3 were determined by single-crystal X-ray diffraction analysis. In addition, complexes 5-7 were tested as defined precatalysts for Pd-catalyzed cyanation of aryl bromides with K4[Fe(CN)6].3H2O in aqueous dioxane. Complex 5 proved the most active and generally applicable, affording the nitrile products in good to excellent yields. The reaction of pentafluorophenyl 1'-(diphenylphosphino)ferrocene-1-carboxylate (4) with omega-aminosulfonic acids H2N(CH2)nSO3H (n = 1-3) in the presence of 4-(dimethylamino)pyridine and triethylamine affords the respective phosphinoferrocene amidosulfonates as crystalline triethylammonium salts, viz., (Et3NH)[Ph2PfcCONH(CH2)nSO3] (1, n = 1; 2, n = 2; 3, n = 3; fc = ferrocene-1,1'-diyl), in good yields. These ligands react smoothly with [PdCl2(cod)] (cod = eta(2):eta(2)-cycloocta-1,5-diene) to give the anionic square-planar bis-phosphine complexes trans-(Et3NH)2[PdCl2(Ph2PfcCONH(CH2)nSO3-kappa P)2] (5, n = 1; 6, n = 2; and 7, n = 3). The chloride-bridged dimer [LPdCl]2, where L is 2-[(dimethylamino-kappa N)methyl]phenyl-kappa C-1 auxiliary ligand, is cleaved with 1 to give (Et3NH)[LPd(Ph2PfcCONHCH2SO(3)-kappa P)] (8), in which the amidosulfonate coordinates as a simple phosphine. A similar reaction of [LPd(OAc)]2 and 1 proceeds under a partial elimination of (Et3NH)OAc to afford a mixture of zwitterionic bis-chelate [LPd(Ph2PfcCONHCH2SO3-kappa O-2,P)] (9) and another Pd(II) complex tentatively formulated as [LPd(OAc)(Ph2PfcCONHCH2SO3-kappa P)] (9a), from which the former complex separates as an analytically pure crystalline solid. All compounds have been characterized by spectroscopic methods and elemental analysis. The crystal structures of 1, 3, 5.2.5CH2Cl2, and 9.2CHCl3 were determined by single-crystal X-ray diffraction analysis. In addition, complexes 5-7 were tested as defined precatalysts for Pd-catalyzed cyanation of aryl bromides with K4[Fe(CN)6].3H2O in aqueous dioxane. Complex 5 proved the most active and generally applicable, affording the nitrile products in good to excellent yields.
dcterms:title
Phosphinoferrocene Amidosulfonates: Synthesis, Palladium Complexes, and Catalytic Use in Pd-Catalyzed Cyanation of Aryl Bromides in an Aqueous Reaction Medium Phosphinoferrocene Amidosulfonates: Synthesis, Palladium Complexes, and Catalytic Use in Pd-Catalyzed Cyanation of Aryl Bromides in an Aqueous Reaction Medium
skos:prefLabel
Phosphinoferrocene Amidosulfonates: Synthesis, Palladium Complexes, and Catalytic Use in Pd-Catalyzed Cyanation of Aryl Bromides in an Aqueous Reaction Medium Phosphinoferrocene Amidosulfonates: Synthesis, Palladium Complexes, and Catalytic Use in Pd-Catalyzed Cyanation of Aryl Bromides in an Aqueous Reaction Medium
skos:notation
RIV/00216208:11310/12:10126165!RIV13-MSM-11310___
n16:predkladatel
n17:orjk%3A11310
n4:aktivita
n18:Z n18:I n18:S
n4:aktivity
I, S, Z(MSM0021620857)
n4:cisloPeriodika
2
n4:dodaniDat
n8:2013
n4:domaciTvurceVysledku
n10:3157962 n10:8116997 n10:9177590
n4:druhVysledku
n20:J
n4:duvernostUdaju
n13:S
n4:entitaPredkladatele
n19:predkladatel
n4:idSjednocenehoVysledku
158520
n4:idVysledku
RIV/00216208:11310/12:10126165
n4:jazykVysledku
n7:eng
n4:klicovaSlova
Pd-catalyzed cyanation; Phosphines; Ferrocene ligands; Amidosulfonate ligands; Palladium
n4:klicoveSlovo
n9:Phosphines n9:Palladium n9:Amidosulfonate%20ligands n9:Ferrocene%20ligands n9:Pd-catalyzed%20cyanation
n4:kodStatuVydavatele
US - Spojené státy americké
n4:kontrolniKodProRIV
[58C202C710BD]
n4:nazevZdroje
Organometallics
n4:obor
n12:CA
n4:pocetDomacichTvurcuVysledku
3
n4:pocetTvurcuVysledku
3
n4:rokUplatneniVysledku
n8:2012
n4:svazekPeriodika
31
n4:tvurceVysledku
Císařová, Ivana Štěpnička, Petr Schulz, Jiří
n4:wos
000299351500026
n4:zamer
n15:MSM0021620857
s:issn
0276-7333
s:numberOfPages
10
n5:doi
10.1021/om2011529
n21:organizacniJednotka
11310