About: Synthesis, Coordination Properties, and Catalytic Use of Phosphinoferrocene Carboxamides Bearing Donor-Functionalized Amide Substituents     Goto   Sponge   NotDistinct   Permalink

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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. (en)
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 (en)
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 (en)
skos:notation
  • RIV/00216208:11310/13:10159365!RIV14-GA0-11310___
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • I, P(GA13-08890S), S, Z(MSM0021620857)
http://linked.open...iv/cisloPeriodika
  • 20
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 109504
http://linked.open...ai/riv/idVysledku
  • RIV/00216208:11310/13:10159365
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • Suzuki cross-coupling; palladium; trans-spanning donors; phosphinoamides; phosphine ligands; ferrocene ligands (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV
  • [31449FC05902]
http://linked.open...i/riv/nazevZdroje
  • Organometallics
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http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 32
http://linked.open...iv/tvurceVysledku
  • Císařová, Ivana
  • Schulz, Jiří
  • Štěpnička, Petr
  • Schneiderová, Barbora
http://linked.open...ain/vavai/riv/wos
  • 000326365900012
http://linked.open...n/vavai/riv/zamer
issn
  • 0276-7333
number of pages
http://bibframe.org/vocab/doi
  • 10.1021/om400282z
http://localhost/t...ganizacniJednotka
  • 11310
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