2-D NMR Spectroscopy of chiral phosphine complexes. Applications to problems related to enantioselective homogeneous catalysis

Pregosin, Paul S.; Trabesinger, Gerald

doi:10.1039/a708568k

Cited by 37 publications

(23 citation statements)

References 60 publications

(31 reference statements)

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“…The performance of complex 1S as a catalyst has already been studied by Kollár et al [41], who described its 1 H NMR temperature-dependent behavior. Other NMR studies on similar complexes have been reported [42][43][44][45][46][47][48][49]. Our data confirm and complement those studies.…”

Section: Platinum Complexessupporting

confidence: 92%

Biological activity of enantiomeric complexes [PtCl2L2] (L2 is aromatic bisphosphanes and aromatic diamines)

et al. 2010

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Enantiomeric complexes of formula [PtCl(2)L(2)] [L(2) is (R)-(+)-BINAP and (S)-(-)-BINAP, where BINAP is 2,2'-bis(diphenylphosphane)-1,1'-binaphthyl, and (R)-(+)-DABN and (S)-(-)-DABN, where DABN is 1,1'-binaphthyl-2,2'-diamine], were tested for their cytotoxic activity against three cancer cell lines and for their ability to bind to the human telomeric sequence folded in the G-quadruplex structure. Similar experiments were carried out on prototypal complexes cisplatin and cis-[PtCl(2)(PPh(3))(2)] for comparison. Platinum complexes containing phosphanes proved less cytotoxic to cancer cell lines and less likely to interact with the nucleobases of the G-quadruplex than those containing amines; in both cases the S-(-) isomer was more active than the R-(+) counterpart. More specifically, whereas all the platinum complexes were able to platinate the G-quadruplex structure from the human telomeric repeat, the extent and sites of platination depended on the nature of the ligands. Complexes containing (bulky) phosphanes interacted only with the adenines of the loops, whereas those containing the less sterically demanding amines interacted with adenines and some guanines of the G-quartet.

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Section: Platinum Complexessupporting

confidence: 92%

Biological activity of enantiomeric complexes [PtCl2L2] (L2 is aromatic bisphosphanes and aromatic diamines)

et al. 2010

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“…In the 1 H NMR spectra, the integrals indicated a dpa: PR 3 ratio of 1:1. HMBC 1 H- 31 P experiments showed that in both complexes the PR 3 ligand is in the trans position relative to a nitrogen atom of the 2,2 0 -dipyridylamine ligand, due to the presence of coupling of one o-H with the PR 3 ligand as described elsewhere [23]. These observations are in agreement with the structures found in the solid state by X-ray crystallography and found for analogous complexes as published previously [24].…”

Section: Resultssupporting

confidence: 86%

Neutral and cationic ruthenium carbonyl complexes [Ru(CO)(2,2′-dipyridylamine)(PR3)Cl2] and [Ru(CO)(N–N)(PPh3)2(H)]Cl: synthesis, structural characterization and transfer-hydrogenation

Cavarzan

Pinheiro

Araujo

2014

Transition Met Chem

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The neutral complexes [Ru(CO)(dpa)(PR 3 )Cl 2 ] (R = Ph (1) or p-tol (2); dpa = 2,2 0 -dipyridylamine) were synthesized by the reaction of [Ru(CO)(dmf)(PR 3 ) 2 Cl 2 ] (dmf = N,N-dimethylformamide) and the dpa ligand, while the cationic carbonyl hydride complexes [Ru(CO) (N-N)(PPh 3 ) 2 (H)]Cl were synthesized by reaction of [Ru(CO)(PPh 3 ) 3 Cl(H)] and the appropriate N-N ligand [N-N = 2,2 0 -bipyridine = bipy (3), 2,2 0 -4,4 0 dimethylbipyridine = dmb (4) and 2,2 0 -dipyridylamine = dpa (5)]. The complexes were characterized by NMR ( 31 P, 1 H and HMBC 1 H-31 P), FTIR, elemental analysis and X-ray diffraction. The molecular structure of [Ru(CO)(dpa)(PPh 3 ) Cl 2 ] (1) was determined by X-ray crystallography. The crystal packing is stabilized by strong (CH 3 )O-HÁÁÁCl and N-HÁÁÁOH(CH 3 ) hydrogen bonds between symmetry-related molecules leading to the formation of dimers. Complexes 1-6 were evaluated as pre-catalysts for the reduction of acetophenone under transfer-hydrogenation conditions using isopropanol as hydrogen source, and conversions up to 86 % in 4 h were achieved.

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“…The syn , syn geometry of the allyl ligand was established in both isomers from NOE cross‐peaks between the lateral allyl signals (δ = 4.69−5.38 and 4.92−5.03 ppm; see Scheme ). This is also suggested by the large values of the coupling constants between the central and lateral allylic protons (10−14 Hz), although this fact alone would not be definite proof 3a. We note, however, that within each allyl ligand, both values of 3 J H,H are not equal which suggests that the allyl group undergoes deformations.…”

Section: Resultsmentioning

confidence: 71%

Palladium Complexes with Chiral Diphospholane Ligands: Comparative Catalytic Properties and Analysis of (η³‐Allyl)palladium Species

et al. 2004

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The chiral diphospholane ligands Duphos (1) and Duxantphos (2), which can be differentiated by their bite angle, were applied to palladium-catalysed asymmetric reactions, essentially allylic alkylations with symmetrically (3a−d) or unsymmetrically (5a,b) substituted allylic acetates as substrates. The most interesting results were found with the first series of substrates in which 2 was more reactive and/or selective than 1. The model complexes of the catalytic intermediates [Pd{(S,S)-1}(η 3 -cyclohexenyl)](BF 4 ) (10) and exo-[Pd{(R,R)-2}(η 3 -cyclohexenyl)](SbF 6 ) (11) could be characterised by X-ray crystallography.

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2-D NMR Spectroscopy of chiral phosphine complexes. Applications to problems related to enantioselective homogeneous catalysis

Cited by 37 publications

References 60 publications

Biological activity of enantiomeric complexes [PtCl2L2] (L2 is aromatic bisphosphanes and aromatic diamines)

Biological activity of enantiomeric complexes [PtCl2L2] (L2 is aromatic bisphosphanes and aromatic diamines)

Neutral and cationic ruthenium carbonyl complexes [Ru(CO)(2,2′-dipyridylamine)(PR3)Cl2] and [Ru(CO)(N–N)(PPh3)2(H)]Cl: synthesis, structural characterization and transfer-hydrogenation

Palladium Complexes with Chiral Diphospholane Ligands: Comparative Catalytic Properties and Analysis of (η³‐Allyl)palladium Species

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2-D NMR Spectroscopy of chiral phosphine complexes. Applications to problems related to enantioselective homogeneous catalysis

Cited by 37 publications

References 60 publications

Biological activity of enantiomeric complexes [PtCl2L2] (L2 is aromatic bisphosphanes and aromatic diamines)

Biological activity of enantiomeric complexes [PtCl2L2] (L2 is aromatic bisphosphanes and aromatic diamines)

Neutral and cationic ruthenium carbonyl complexes [Ru(CO)(2,2′-dipyridylamine)(PR3)Cl2] and [Ru(CO)(N–N)(PPh3)2(H)]Cl: synthesis, structural characterization and transfer-hydrogenation

Palladium Complexes with Chiral Diphospholane Ligands: Comparative Catalytic Properties and Analysis of (η3‐Allyl)palladium Species

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Palladium Complexes with Chiral Diphospholane Ligands: Comparative Catalytic Properties and Analysis of (η³‐Allyl)palladium Species