2129-31-9Relevant articles and documents
Silica-Supported Phosphine–Gold Complexes as an Efficient Catalytic System for a Dearomative Spirocyclization
Bibal, Brigitte,Buffière, Sonia,Cao, Zhen,Nlate, Sylvain,Oda, Reiko,Pouget, Emilie,Scalabre, Antoine
supporting information, p. 427 - 433 (2020/12/03)
The combination of metal catalyst and inorganic silica frameworks provides a greener approach to recyclable catalysis. In this study, three phosphine–gold chloride complexes have been successfully covalently grafted onto chiral silica nanohelices. The resulting 3D ensembles showed chiroptical properties that allowed the monitoring of the supported ligands. The heterogeneous gold chloride catalysts in cooperation with silver triflate exhibited high reactivity in various reactions, especially in the spirocyclization of aryl alkynoate esters, for which a catalytic loading of 0.05 mol % could be employed. The heterogeneous catalysts could be easily recovered and recycled seven or eight times without any loss of efficiency. By adding more silver triflate, 25 cycles with full conversion were achieved owing to a complex catalytic system based on silica and metallic species.
Efficient potassium hydroxide promoted P-arylation of aryl halides with diphenylphosphine
Chen, Jin,Dai, Bencai,Liu, Changchun,Shen, Zhihao,Zhou, Yang
, (2021/06/26)
A simple synthetic method of triarylphosphine compounds by KOH-promoted P-Arylation reaction of aryl halides with diphenylphosphine is presented. Notably, this transformation could smoothly proceed with high yields under transition-metal-free and mild reaction conditions. In addition, this protocol is valuable for industrial application due to the convenient operation and readily accessible aromatic halides. A possible explanation of the reaction mechanism was proposed based on the experimental data.
Electrophilic Phosphonium Cation-Mediated Phosphane Oxide Reduction Using Oxalyl Chloride and Hydrogen
Stepen, Arne J.,Bursch, Markus,Grimme, Stefan,Stephan, Douglas W.,Paradies, Jan
supporting information, p. 15253 - 15256 (2018/10/24)
The metal-free reduction of phosphane oxides with molecular hydrogen (H2) using oxalyl chloride as activating agent was achieved. Quantum-mechanical investigations support the heterolytic splitting of H2 by the in situ formed electrophilic phosphonium cation (EPC) and phosphane oxide and subsequent barrierless conversion to the phosphane and HCl. The reaction can also be catalyzed by the frustrated Lewis pair (FLP) consisting of B(2,6-F2C6H3)3 and 2,6-lutidine or phosphane oxide as Lewis base. This novel reduction was demonstrated for triaryl and diaryl phosphane oxides providing access to phosphanes in good to excellent yields (51–93 %).
Ruthenium arene complexes with triphenylphosphane ligands: Cytotoxicity towards pancreatic cancer cells, interaction with model proteins, and effect of ethacrynic acid substitution
Biancalana, Lorenzo,Pratesi, Alessandro,Chiellini, Federica,Zacchini, Stefano,Funaioli, Tiziana,Gabbiani, Chiara,Marchetti, Fabio
supporting information, p. 14574 - 14588 (2017/11/28)
The ruthenium-arene complexes [(η6-p-cymene)RuCl2(κP-PPh2(4-C6H4CO2H))], 1, [(η6-p-cymene)RuCl(κ2P,O-PPh2(2-C6H4CO2))], 2, [(η6-p-cymene)RuCl2(κP-PPh2(2-C6H4OCO-EA))], 3, and [(η6-p-cymene)RuCl2(κP-PPh2(4-C6H4CO2CH2CH2OCO-EA))], 4 (EA-CO2H = ethacrynic acid), were synthesized in good to high yields and characterized by analytical techniques, IR, UV-Vis and multinuclear NMR spectroscopy, and single crystal X-ray diffraction in the cases of 1 and 2. The unstable compounds [(η6-arene)RuCl2(κP-PPh2(2-C6H4CO2CH2CH2OCO-EA))] (arene = p-cymene, 5a; arene = C6H6, 5b) were obtained and identified in solution by NMR. Electrochemical and spectro-electrochemical experiments were performed in order to assess the redox behaviour of 1-4 in CH2Cl2. The in vitro cytotoxicity of 1-4 was determined on the human pancreatic cancer cell line BxPC3 and the mouse embryo fibroblast Balb/3T3 Clone A31 cell line, the latter acting as a model for normal cells. Furthermore, the interaction of 1, 3 and 4 with two model proteins was investigated by high resolution ESI-MS.
A rhodium triphenylphosphine catalyst for alkene hydrogenation supported on neat superparamagnetic iron oxide nanoparticles
Dehe, Daniel,Wang, Lei,Müller, Melanie K.,D?rr, Gunder,Zhou, Zhou,Klupp-Taylor, Robin N.,Sun, Yu,Ernst, Stefan,Hartmann, Martin,Bauer, Matthias,Thiel, Werner R.
, p. 127 - 136 (2015/03/05)
A phosphonic acid functionalized triphenylphosphine rhodium complex was synthesized and grafted onto neat superparamagnetic iron oxide nanoparticles. The material was investigated by elemental analysis, IR spectroscopy, thermogravimetric analysis, XRD, N2-physisorption analyses, and TEM measurements. The obtained hybrid material could be used as a catalyst for the hydrogenation of alkenes with excellent yields and a broad substrate scope. The catalyst can be reused ten times without any loss of activity. According to the results from X-ray absorption spectroscopy, it is likely that formation of Rh nanoparticles occurs during the reaction.
Ruthenium and Osmium Complexes of Phosphine-Porphyrin Derivatives as Potential Bimetallic Theranostics: Photophysical Studies
Harvey, Pierre D.,Tasan, Semra,Gros, Claude P.,Devillers, Charles H.,Richard, Philippe,Le Gendre, Pierre,Bodio, Ewen
supporting information, p. 1218 - 1227 (2015/04/27)
A series of (η6-p-cymene)ruthenium(II)- and osmium(II) complexes of porphyrin-phosphane derivatives have been synthesized as potential bimetallic theranostic candidates. The photophysical and electrochemical properties were investigated, and th
Novel heterobimetallic radiotheranostic: Preparation, activity, and biodistribution
Adriaenssens, Louis,Liu, Qiang,Chaux-Picquet, Fanny,Tasan, Semra,Picquet, Michel,Denat, Franck,Le Gendre, Pierre,Marques, Fernanda,Fernandes, Célia,Mendes, Filipa,Gano, Lurdes,Campello, Maria Paula Cabral,Bodio, Ewen
supporting information, p. 1567 - 1573 (2014/07/21)
A novel RuII(arene) theranostic complex is presented. It is based on a 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid macrocycle bearing a triarylphosphine and can be tracked in vivo by using the γ emission of 153Sm atoms.
Effect of triarylphosphane ligands on the rhodium-catalyzed hydrosilylation of alkene
Xue, Mei,Li, Jiayun,Peng, Jiajian,Bai, Ying,Zhang, Guodong,Xiao, Wenjun,Lai, Guoqiao
, p. 120 - 126 (2014/02/14)
A series of triarylphosphanes (1a, 2a, 3a, 4a, 5a, 6a, 7a, 8a, 9a, 10a, 11a) have been synthesized. An X-ray crystal structure analysis of (2-bromophenyl)diphenylphosphane (1a) unambiguously confirmed the constitution of the functionalized phosphane. The hydrosilylation reaction of styrene with triethoxysilane catalyzed with RhCl3/triarylphosphane was studied. In comparison with the classic Wilkinson's catalyst, rhodium complexes with functionalized triarylphosphane ligands are characterized by a very high catalytic effectiveness for the hydrosilylation of alkene. Among these catalysts tested, RhCl3/diphenyl(2-(trimethylsilyl)phenyl)phosphane (8a) exhibited excellent catalytic properties. Using this silicon-containing phosphane ligand for the rhodium-catalyzed hydrosilylation of styrene, both higher conversion of alkene and higher β-adduct selectivity were obtained than with Wilkinson's catalyst.
BODIPY-phosphane as a versatile tool for easy access to new metal-based theranostics
Tasan, Semra,Zava, Olivier,Bertrand, Beno?t,Bernhard, Claire,Goze, Christine,Picquet, Michel,Le Gendre, Pierre,Harvey, Pierre,Denat, Franck,Casini, Angela,Bodio, Ewen
supporting information, p. 6102 - 6109 (2013/06/26)
A new BODIPY-phosphane was synthesized and proved to be a versatile tool for imaging organometallic complexes. It also led to easy access to a new family of theranostics, featuring gold, ruthenium and osmium complexes. The compounds' cytotoxicity was test
Catalysts for Suzuki polycondensation: Ionic and "quasi-ionic" amphipathic palladium complexes with self-phase-transfer features
Li, Jing,Fu, Hongwei,Hu, Pan,Zhang, Zilong,Li, Xiao,Cheng, Yanxiang
supporting information, p. 13941 - 13944,4 (2020/09/16)
Poly(9,9-dioctylfluorene) (PFO) with Mn values above 100 000 g mol-1 in a toluene/water system and Mn values up to 600 000 g mol-1 in a THF/water system has been obtained by improved Suzuki polycondensation using a new kind of amphipathic palladium catalyst with self-phase-transfer features, which could overcome the disadvantage caused by the immiscible biphasic mixture and accelerate the transmetalation step (see figure). Copyright
