Reactions of benzyldiphenylphosphine with Pd(II) sources on silica gel

Stepanova, Valeria A.; Egan, Layne M.; Stahl, Lothar; Smoliakova, Irina P.

doi:10.1016/j.jorganchem.2011.06.026

Cited by 12 publications

(3 citation statements)

References 69 publications

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“…Rather surprisingly, the structures of 12a and 12c are the first to be reported for bromo‐bridged dimers with cyclometallated benzylphosphanes. Indeed, there are only a few structures of chloro‐bridge dimers,, including chloro‐analogue of 12a , described by Smoliakova and co‐workers . The parameters of 12a and 12b are similar to those reported structures except the Pd–Br distances which as expected are longer than the Pd–Cl.…”

Section: Resultssupporting

confidence: 73%

Cyclopalladated Compounds with Polyhalogenated Benzylphosphanes for the Mizoroki‐Heck Reaction

et al. 2020

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Nine partially halogenated benzylphosphanes Ar X CH 2 PR 2 (Ar X = 3,6-dichlorophenyl, 3,6-difluorophenyl and 3,4,5-trifluorophenyl; R = Ph, Cy, iPr) have been prepared and reacted with palladium acetate to obtain the cyclometallated dimers [Pd(μ-OAc)(κ 2-C,P-Ar X CH 2 PR 2)] 2. The acetate bridge has been exchanged by bromide using lithium bromide and the obtained dimers have been thoroughly characterised. The dimers with the non-halogenated phosphanes PhCH 2 PR 2 (R = Ph, iPr) have also been prepared.

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Section: Resultssupporting

confidence: 73%

Cyclopalladated Compounds with Polyhalogenated Benzylphosphanes for the Mizoroki‐Heck Reaction

et al. 2020

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“…In 2 , the sac ligand is cis to the chlorido ligand, but it is trans to chlorido in 4 . The PdN and PdP bond distances in 3 are similar to those in cis ‐[Pd(sac) 2 (ter‐phos) 2 ], 35 and cis ‐[PdCl 2 (PPh 2 Bz) 2 ] 36 . The PtP bond distances in 4 are remarkably bigger than those in 2 , correlating with the cone angles of PPh 2 Py and PPh 2 Bz (145° and 152°, respectively) 37 .…”

Section: Resultsmentioning

confidence: 65%

“…The Pd N and Pd P bond distances in 3 are similar to those in cis-[Pd(sac) 2 (ter-phos) 2 ], 35 and cis-[PdCl 2 (PPh 2 Bz) 2 ]. 36 The Pt P bond distances in 4 are remarkably bigger than those in 2, correlating with the cone angles of PPh 2 Py and PPh 2 Bz (145 and 152 , respectively). 37 On the other hand, the Pt Cl and Pt N bond distances in 2 are markedly longer than the same bonds in 4, indicating the greater trans effect of PPh 2 Py compared with both sac and chlorido ligands.…”

Section: X-ray Structuresmentioning

confidence: 96%

Pd(II) and Pt(II) saccharinate complexes with two phosphine derivatives: Synthesis, anticancer and antiangiogenic activities

Icsel,

Yilmaz,

Aygun

et al. 2024

Applied Organom Chemis

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As clinically used anticancer Pt(II) drugs have severe side effects, there is a growing interest for new metal complexes with great potential for cancer therapy. The current work aimed to prepare and characterize new Pd(II) and Pt(II) saccharinate (sac) complexes bearing pyridyl‐ and benzyldiphenylphosphines (PPh2Py and PPh2Bz, respectively), cis‐[Pd(sac)2(PPh2Py)2] (1), cis‐[PtCl(sac)(PPh2Py)2]·0.5DMF (2), cis‐[Pd(sac)2(PPh2Bz)2]·DMF (3) and trans‐[PtCl(sac)(PPh2Bz)2] (4) as promising anticancer and antiangiogenic drugs. The anticancer activity of the complexes was screened against seven cancer cell lines including HCT116 (colon), HepG2 (liver), MDA‐MB‐231 (breast), PANC‐1 (pancreatic), A549 (lung), C6 (glioma), DU145 (prostate) and normal human lung epithelial cells (BEAS‐2B). 1 and 2 did not show biological activity below 20 μM at 48 h, whereas 3 and 4 displayed significant cytotoxic effect on the cancer cells. 4 was the most potent complex (IC50 = 2.2–12.1 μM) and displayed much greater cytotoxicity than cisplatin in all the cancer cell lines. 4 caused apoptosis in HCT116 cells as evidenced by annexin V positivity and caspase 3/7 activity assays. Furthermore, the inhibition of antiapoptotic Bcl‐2 proteins by the complex suggested the intrinsic apoptosis. In addition, 4 greatly enhanced generation of intracellular reactive oxygen species (ROS) and consequently caused remarkable DNA double‐strand breaks in HCT116 cells. Moreover, the chick chorioallantoic membrane (CAM) assay was used to evaluate antiangiogenic potential of 4. The complex effectively inhibited angiogenesis at a dose of 50 ng, suggesting it as a promising multi‐targeted agent for antiangiogenic cancer treatment.

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Benzyl Diphenylphosphine

Karp

2021

Encyclopedia of Reagents for Organic Synthesis

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Reactions of benzyldiphenylphosphine with Pd(II) sources on silica gel

Cited by 12 publications

References 69 publications

Cyclopalladated Compounds with Polyhalogenated Benzylphosphanes for the Mizoroki‐Heck Reaction

Cyclopalladated Compounds with Polyhalogenated Benzylphosphanes for the Mizoroki‐Heck Reaction

Pd(II) and Pt(II) saccharinate complexes with two phosphine derivatives: Synthesis, anticancer and antiangiogenic activities

Benzyl Diphenylphosphine

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