Convenient synthetic routes to bidentate and monodentate 2-, 3- and 4-pyridyl phosphines: potentially useful ligands for water-soluble complex catalysts

Bowen, Richard J.; Garner, A. Christopher; Berners‐Price, Susan J.; Jenkins, Ian D.; Sue, Rodney E.

doi:10.1016/s0022-328x(97)00722-5

Cited by 52 publications

(41 citation statements)

References 13 publications

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“…The phosphite products were readily isolated after a purification over a short alumina column. Monodentate ligands a-i were commercially available or prepared via known or standard procedures (see Section 4) [12].…”

Section: Resultsmentioning

confidence: 99%

Supraphos: A supramolecular strategy to prepare bidentate ligands

Reek¹,

Röder²,

Goudriaan³

et al. 2005

Journal of Organometallic Chemistry

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Herein, we report a new strategy for the preparation of chelating bidentate ligands, which involves the mixing of two mondentate ligands functionalized with complementary binding sites. The assembly process is based on selective metal-ligand interactions employing phosphite zinc(II) porphyrins 1-6 and the nitrogen-containing phosphorus ligands b-i (Scheme 1). Only 14 monodentate ligands were utilized to generate a library of 48 palladium catalysts based on supraphos-type bidentate ligands. The characterization of rhodium complexes based on representative Supramolecular bidentate ligands and the comparison of their performance in the hydroformylation of styrene will be presented. The current library of catalysts was tested in the asymmetric palladium-catalyzed alkylation of rac-1,3-diphenyl-2-propenyl acetate, which resulted in a large variety in the observed enantioselectivity for the different catalysts. Importantly, small variations in the supraphos building blocks, lead to large differences in the enantioselectivity imposed by the catalyst, the most selective catalyst producing 97% ee.

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Section: Resultsmentioning

confidence: 99%

Supraphos: A supramolecular strategy to prepare bidentate ligands

Reek¹,

Röder²,

Goudriaan³

et al. 2005

Journal of Organometallic Chemistry

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“…The other half is either generated by a 4 2 symmetry element (for 2) or an inversion centre (for all other structures) respectively. *** PUT FIGURE 2 HERE *** (10). We were able to obtain red crystals of 10 as solvate ( Figure 6).…”

Section: Solid State Structuresmentioning

confidence: 91%

“…[5,6] To circumvent the lipophilicity related side effects, more hydrophilic diphos complexes have to be developed and one approach is to replace the phenyl rings of dppe by pyridine. [7][8][9][10][11] We have developed imidazole-based water-soluble phosphane ligands for application as enzyme models and for biomedical applications in the past. [12,13] Based upon our previous findings, we herein report on synthetic routes towards diverse imidazolyl as well as thiazolyl substituted diphosphane ligands, which should exhibit similar properties concerning their use in biological media.…”

Section: Introductionmentioning

confidence: 99%

Novel multitopic diphos-type ligands.

Kunz

Wetzel

Bongartz

et al. 2010

Journal of Organometallic Chemistry

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Seven novel imidazole and thiazole derivatives of diphos-type ligands are presented. They are of the general structure R2P(CH2)(2)PR2, where R is imidazol-2-yl (1), 1-methylimidazol-2-yl (2), 1-methyl-benzimidazol-2-yl (3), 1-methylimidazol-5-yl (4), 2-isopropylimidazol-4(5)-yl (5), thiazol-2-yl (6), benzothiazol-2-yl (7), thiazol-4-yl (8) or thiazol-5-yl (9). Syntheses involved direct metallation or halogenmetal exchange reactions. Their solubility, especially in aqueous solution, is strongly dependent on the nature of the substituents as is their partition coefficient log D. The crystal structures of compounds 2, 3, 7a and 9 as well as the structure of the rhodium complex (2)(2) , Corinna Wetzel [a] , Melanie Bongartz [a] , Anna-Louisa Noffke [a] and Bernhard Spingler

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“…The bidentate pyridyl phosphine ligands [14] and their Au(I) or Ag(I) complexes were synthesised according to published procedures for [Au(dppe) 2 ]Cl (SMI) [18], [Au(d4pype) 2 ]Cl (SMII), [Au(d2pype) 2 ] 2 Cl 2 (SMIV) and…”

Section: Chemicals and Reagentsmentioning

confidence: 99%

“…1). We retained aromatic substituents, which appear to be important for antitumour activity [12], but replaced some, or all by hydrophilic pyridyl groups [13][14][15][16]. As a result, a series of 1:2 adducts of Au(I) and Ag(I) with bidentate pyridylphosphines compounds were prepared with potential for activity in cisplatin-resistant ovarian cancer and reduced hepatotoxicity relative to [Au(dppe) 2 ]Cl [17].…”

Section: Introductionmentioning

confidence: 99%