23081-74-5Relevant articles and documents
Chelate complexes of phosphorus-nitrogen ligands. 1. Deprotonation, cis-trans isomerism, and anion-catalyzed isomerization in platinum(II) complexes of (o-aminophenyl)diphenylphosphine
Cooper, Mervyn K.,Michael Downes
, p. 880 - 884 (1978)
The new hybrid ligand (o-aminophenyl)diphenylphosphine (PNH2) has been synthesized and bis-ligand chelate complexes of platinum(II) have been prepared. Facile deprotonation of the coordinated amino group has allowed the preparation of both cis and trans isomers of [Pt(PNH2)2]X2, [Pt(PNH-)(PNH2)]X, and [Pt(PNH-)2] (X- is a noncoordinating anion and PNH- is the conjugate base of PNH2). The stereochemistries have been assigned using 31P NMR spectroscopy. The first observation of anion-catalyzed isomerization in square-planar complexes is reported.
Playing with Pearson's concept: Orthogonally functionalized 1,4-diaza-1,3-butadienes leading to heterobinuclear complexes
Neu,Di Martino-Fumo,Oelkers,Sun,Neuba,Gerhards,Thiel
, p. 9643 - 9656 (2018)
By reacting 1,2-diketones and ortho- diphenylphosphinoyl aniline in the presence of zinc(ii) as a templating agent, cationic zinc(ii) complexes of novel phosphine oxide functionalized 1,4-diaza-1,3-butadiene ligands are acessible. Herein the zinc(ii) site is bound to all four donor atoms of the ligand. Depending on the flexibility of the 1,4-diaza-1,3-butadiene backbone, the bonds to zinc(ii) from the 1,4-diaza-1,3-butadiene donors can be broken. Reaction with oxalate cleaves the zinc(ii) coordination completely and makes accessible the free ligands possessing orthogonal (N,N: soft; O,O: hard) sets of donor sites. This allows for the specific coordination of soft and hard Lewis acids and thus for the generation of heterobimetallic complexes, here exemplarily shown for the combination of palladium(ii) (soft) and zinc(ii) (hard) centres.
Chelation-Assisted Interrupted Copper(I)-Catalyzed Azide-Alkyne-Azide Domino Reactions: Synthesis of Fully Substituted 5-Triazenyl-1,2,3-triazoles
García López, Jesús,Iglesias, María José,López Ortiz, Fernando,Navarro, Yolanda
supporting information, p. 334 - 339 (2021/01/13)
We describe the synthesis of 1,4-(disubstituted)-5-triazenyl-1,2,3-triazoles through a ligand-free domino copper(I)-catalyzed azide-alkyne-azide process of chelating aryl azides bearing N-P═O, P═O, and SO3H groups at the ortho position with a wide variety of acetylenes. DFT calculations reveal that Cu-chelation is a crucial factor in the interception of the CuAAC intermediate by the azide. The crystal structure of the catalytic species has been determined by X-ray diffraction.
Copper-Catalyzed C?P Cross-Coupling of (Cyclo)alkenyl/Aryl Bromides and Secondary Phosphine Oxides with in situ Halogen Exchange
Stankevi?, Marek,Wo?nicki, Pawe?
, p. 3484 - 3491 (2021/07/22)
An efficient protocol for concurrent tandem halogen exchange/C?P cross-coupling of cycloalkenyl bromides and secondary phosphine oxides has been developed. The catalytic system is based on cheap and air-stable copper(I) iodide as the precatalyst, commercially available N,N’-dimethylethylenediamine as the ligand, and Cs2CO3 or K2CO3 as the base. The use of sodium iodide as an additive reduces the excessive use of organic bromides to near-stoichiometric by promoting the in situ transformation to the corresponding iodides. Diarylphosphine oxides undergo cycloalkenylation with 35–99 % yields and dicyclohexylphosphine oxide with 30–53 % yields. In the case of acyclic alkenyl bromides the cross-coupling products undergo conjugate addition of diphenylphosphine oxide and satisfying yields are observed only for internal olefins. In the case of aryl bromides satisfying yields (43–72 %) are observed only for sterically unhindered arenes or arenes possessing an ortho-directing group. Cycloalkenylphosphine oxides prepared in the cross-coupling reaction undergo base-catalyzed and base-promoted conjugate addition to give bis(phosphinoyl)cycloalkanes.
Scalable Rhodium(III)-Catalyzed Aryl C?H Phosphorylation Enabled by Anodic Oxidation Induced Reductive Elimination
Wu, Zheng-Jian,Su, Feng,Lin, Weidong,Song, Jinshuai,Wen, Ting-Bin,Zhang, Hui-Jun,Xu, Hai-Chao
supporting information, p. 16770 - 16774 (2019/11/03)
Transition metal catalyzed C?H phosphorylation remains an unsolved challenge. Reported methods are generally limited in scope and require stoichiometric silver salts as oxidants. Reported here is an electrochemically driven RhIII-catalyzed aryl C?H phosphorylation reaction that proceeds through H2 evolution, obviating the need for stoichiometric metal oxidants. The method is compatible with a variety of aryl C?H and P?H coupling partners and particularly useful for synthesizing triarylphosphine oxides from diarylphosphine oxides, which are often difficult coupling partners for transition metal catalyzed C?H phosphorylation reactions. Experimental results suggest that the mechanism responsible for the C?P bond formation involves an oxidation-induced reductive elimination process.
Synthesis and biological evaluation of vanadium complexes as novel anti-tumor agents
Lu, Ling-Pan,Suo, Feng-Zhi,Feng, Ya-Li,Song, Li-Li,Li, Ying,Li, Yang-Jie,Wang, Kai-Ti
, p. 1 - 10 (2019/05/15)
A class of vanadium complexes were prepared and investigated for their antiproliferative effects by MTT assay. The structure-activity relationship was extensively studied through the ligand variation. The results showed that the synthetic vanadium complexes demonstrated moderate to good antiproliferative activities against the four cancer cell lines including MGC803, EC109, MCF7 and HepG2, respectively. Of note was that most of the complexes showed preferential growth inhibitory activity to some degree toward gastric cancer line MGC803. Among them, complex 19 exhibited the most and broad-spectrum proliferative inhibition against the tested cell lines. In addition, mechanism studies illustrated that complex 19 could prevent the colony formation, migration and EMT process, as well as induce apoptosis of MGC803 cells. Furthermore, Western blot experiments revealed that the expression of apoptosis-related proteins changed, including up-regulation of Bax, PARP and caspase-3/9, as well as down-regulation of Bcl-2.
Novel topoisomerase I inhibitors. Syntheses and biological evaluation of phosphorus substituted quinoline derivates with antiproliferative activity
Alonso, Concepción,Fuertes, María,Martín-Encinas, Endika,Selas, Asier,Rubiales, Gloria,Tesauro, Cinzia,Knudssen, Birgitta K.,Palacios, Francisco
, p. 225 - 237 (2018/03/09)
This work describes the synthesis of 1,2,3,4-tetrahydroquinolinylphosphine oxides, phosphanes and phosphine sulfides as well as that of quinolinylphosphine oxides and phosphine sulfides, which were synthesized in good to high overall yield. The synthetic
Coordination of P(X)-modified (X = O, S) N-aryl-carbamoylmethylphosphine oxides and sulfides with Pd(II) and Re(I) ions: Facile formation of 6,6-membered pincer complexes featuring atropisomerism
Aleksenko,Sharova,Artyushin,Aleksanyan,Klemenkova,Nelyubina,Petrovskii,Kozlov,Odinets
, p. 168 - 179 (2013/04/10)
Direct acetylation of (thio)phosphorylated anilines 1a,b with in situ generated Ph2P(O)CH2C(O)Cl or sequential treatment of 1a,b with chloroacetyl chloride and Ph2PSNa resulted in novel oligodentate ligands, namely, P(X)-m
Effective modular assembling of novel ligands starting from (Thio)phosphorylated anilines
Kozlov, Vladimir A.,Aleksenko, Valentina Yu.,Aleksanyan, Diana V.,Sharova, Elena V.,Artyushin, Oleg I.,Odinets, Irina L.
, p. 79 - 83 (2013/07/05)
A series of novel oligodentate ligands has been designed by the modular assembly of ortho-(thio)phosphorylated anilines with a range of commercially available carbonyl compounds. The new ligands readily form complexes with a series of metal ions (Pd(II), Cu(II), Ni(II), and Re(I)) both in neutral and deprotonated forms, providing OO, SN, ONO, SNO, SNS, SNN, and ONN donor sets. The structure and composition of the resulting complexes depend on the nature and mutual disposition of the donating groups as well as on the reaction conditions.
Ni(II)/Zn catalyzed reductive coupling of aryl halides with diphenylphosphine oxide in water
Zhang, Xinghua,Liu, Huizhi,Hu, Xiaomei,Tang, Guo,Zhu, Jun,Zhao, Yufen
supporting information; experimental part, p. 3478 - 3481 (2011/09/13)
P-Arylation in water has been developed via cross-coupling of aryl halides with diphenylphosphine oxide (Ph2P(O)H) and (RP)-(-)- menthyl benzylphosphinate catalyzed by NiCl2?6H2O/Zn under relatively mild conditions.
