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Statements

Subject Item
n2:RIV%2F00216208%3A11310%2F13%3A10159365%21RIV14-GA0-11310___
rdf:type
skos:Concept n16:Vysledek
rdfs:seeAlso
http://dx.doi.org/10.1021/om400282z
dcterms:description
Phosphinoferrocene carboxamides bearing donor-functionalized substituents at the amide nitrogen, Ph2PfcCONH(CH2)nY (Y/n = NMe2/2 (1), NMe2/3 (2), PPh2/2 (3), and PPh2/3 (4); fc = ferrocene-1,1'-diyl), were obtained by amide coupling reactions of 1'-(diphenylphosphino)ferrocene-1-carboxylic acid (Hdpf) with the respective amines and structurally characterized. Amide 1 was further converted to the corresponding omega-azoniaalkyl amidophosphine [Ph2PfcCONHCH2CH2NMe3]X (7; X = Cl/I). Amides 1 and 3, possessing the shorter ethane-1,2-diyl linker, reacted smoothly with [PdCl2(cod)] (cod = cyclocta-1,5-diene) to give the respective trans-chelate complexes, trans-[PdCl2(L-kappa P-2,Y)] (8: L = 1; 9: L = 3). The homologous donors 2 and 4 showed more complicated coordination behavior, affording mixtures of several Pd(II) complexes under similar conditions. Compounds 1, 3, and 7 were further evaluated as ligands for Pd-catalyzed Suzuki-Miyaura cross-coupling using 4-bromoacetophenone and phenylboronic acid as model substrates. In dioxane, the yields of the coupling product decreased in the order 3 > 1 > 7, presumably due to different donor ability of these ligands (type of donor atoms; PP > PN > PN+). The catalytic performance in pure water was different: The yields were generally lower and the order of ligands changed to 3 > 7 > 1. Phosphinoferrocene carboxamides bearing donor-functionalized substituents at the amide nitrogen, Ph2PfcCONH(CH2)nY (Y/n = NMe2/2 (1), NMe2/3 (2), PPh2/2 (3), and PPh2/3 (4); fc = ferrocene-1,1'-diyl), were obtained by amide coupling reactions of 1'-(diphenylphosphino)ferrocene-1-carboxylic acid (Hdpf) with the respective amines and structurally characterized. Amide 1 was further converted to the corresponding omega-azoniaalkyl amidophosphine [Ph2PfcCONHCH2CH2NMe3]X (7; X = Cl/I). Amides 1 and 3, possessing the shorter ethane-1,2-diyl linker, reacted smoothly with [PdCl2(cod)] (cod = cyclocta-1,5-diene) to give the respective trans-chelate complexes, trans-[PdCl2(L-kappa P-2,Y)] (8: L = 1; 9: L = 3). The homologous donors 2 and 4 showed more complicated coordination behavior, affording mixtures of several Pd(II) complexes under similar conditions. Compounds 1, 3, and 7 were further evaluated as ligands for Pd-catalyzed Suzuki-Miyaura cross-coupling using 4-bromoacetophenone and phenylboronic acid as model substrates. In dioxane, the yields of the coupling product decreased in the order 3 > 1 > 7, presumably due to different donor ability of these ligands (type of donor atoms; PP > PN > PN+). The catalytic performance in pure water was different: The yields were generally lower and the order of ligands changed to 3 > 7 > 1.
dcterms:title
Synthesis, Coordination Properties, and Catalytic Use of Phosphinoferrocene Carboxamides Bearing Donor-Functionalized Amide Substituents Synthesis, Coordination Properties, and Catalytic Use of Phosphinoferrocene Carboxamides Bearing Donor-Functionalized Amide Substituents
skos:prefLabel
Synthesis, Coordination Properties, and Catalytic Use of Phosphinoferrocene Carboxamides Bearing Donor-Functionalized Amide Substituents Synthesis, Coordination Properties, and Catalytic Use of Phosphinoferrocene Carboxamides Bearing Donor-Functionalized Amide Substituents
skos:notation
RIV/00216208:11310/13:10159365!RIV14-GA0-11310___
n16:predkladatel
n17:orjk%3A11310
n3:aktivita
n11:Z n11:S n11:P n11:I
n3:aktivity
I, P(GA13-08890S), S, Z(MSM0021620857)
n3:cisloPeriodika
20
n3:dodaniDat
n9:2014
n3:domaciTvurceVysledku
n6:3157962 n6:8116997 n6:9177590 n6:1489208
n3:druhVysledku
n14:J
n3:duvernostUdaju
n10:S
n3:entitaPredkladatele
n18:predkladatel
n3:idSjednocenehoVysledku
109504
n3:idVysledku
RIV/00216208:11310/13:10159365
n3:jazykVysledku
n22:eng
n3:klicovaSlova
Suzuki cross-coupling; palladium; trans-spanning donors; phosphinoamides; phosphine ligands; ferrocene ligands
n3:klicoveSlovo
n4:palladium n4:phosphine%20ligands n4:phosphinoamides n4:trans-spanning%20donors n4:ferrocene%20ligands n4:Suzuki%20cross-coupling
n3:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n3:kontrolniKodProRIV
[31449FC05902]
n3:nazevZdroje
Organometallics
n3:obor
n19:CA
n3:pocetDomacichTvurcuVysledku
4
n3:pocetTvurcuVysledku
4
n3:projekt
n21:GA13-08890S
n3:rokUplatneniVysledku
n9:2013
n3:svazekPeriodika
32
n3:tvurceVysledku
Štěpnička, Petr Schneiderová, Barbora Schulz, Jiří Císařová, Ivana
n3:wos
000326365900012
n3:zamer
n15:MSM0021620857
s:issn
0276-7333
s:numberOfPages
12
n8:doi
10.1021/om400282z
n13:organizacniJednotka
11310