Platinum(II) complexes incorporating racemic and optically active 1-alkyl-3-phospholene P-ligands: Synthesis, stereostructure, NMR properties and catalytic activity

Bagi, Péter; Kovács, Tamara; Szilvási, Tibor; Pongrácz, Péter; Kollár, László; Drahos, László; Fogassy, Elemér; Keglevich, György

doi:10.1016/j.jorganchem.2013.03.045

Cited by 26 publications

(19 citation statements)

References 39 publications

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“…The reduction of tertiary phosphine oxides to phosphines is applied to many syntheses, e.g., in the final step of the preparation of P-ligands [1][2][3][4][5] or during the regeneration of triphenylphosphine from triphenylphosphine oxide formed in the Wittig-or the Appel reaction. It has been a challenge to develop catalytic versions of these reactions involving the recycling of the waste cyclic phosphine oxides in in situ reduction [6].…”

Section: Introductionmentioning

confidence: 99%

The Deoxygenation of Phosphine Oxides under Green Chemical Conditions

2014

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The deoxygenation of a few diaryl‐phenylphosphine oxides, dimethyl‐phenylphosphine oxide, and 3‐methyl‐1‐phenyl‐3‐phospholene 1‐oxide was studied by phenylsilane, tetramethyldisiloxane (TMDS), and polymethylhydrosiloxane (PMHS) under conventional or microwave (MW) heating, in toluene or in the absence of any solvent at different temperatures. It was found that the deoxygenation with TMDS or PMHS under MW and solvent‐free conditions may be the method of choice and provides a green chemical approach.

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Section: Introductionmentioning

confidence: 99%

The Deoxygenation of Phosphine Oxides under Green Chemical Conditions

2014

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“…1-Isopropyl-3-methyl-3-phospholene 1-oxide (3) was prepared by extending the synthetic method elaborated for other alkyl-and aryl-3-methyl-3-phospholene oxides [37,47,49].…”

Section: Synthesis and Resolution Of 1-isopropyl-3-methyl-3-phospholementioning

confidence: 99%

“…We have also reported the synthesis of a few racemic and optically active borane and platinum-complexes bearing aryl-and alkyl-3-phospholene ligands. The 3-phospholene -platinum complexes were applied as catalysts in the asymmetric hydroformylation of styrene and enantioselectivities up to 29% were obtained [45][46][47][48].…”

Section: Introductionmentioning

confidence: 99%

A study on the optical resolution of 1-isopropyl-3-methyl-3-phospholene 1-oxide and its use in the synthesis of borane and platinum complexes

Bagi

Juhász

Timári

et al. 2015

Journal of Organometallic Chemistry

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A 1-isopropyl-3-phospholene 1-oxide was prepared and the two enantiomers were isolated from the racemate by resolution using optically active TADDOL derivatives or the acidic Ca 2+ salts of (-)-O,O-diaroyl-(2R,3R)-tartaric acids. The single crystal X-ray structure of the 2 1-isopropyl-3-phospholene oxide -spiro-TADDOL 1:2 associate revealed the mode of binding between the host and guest molecules. The role of the interactions between the three molecules was supported not only by the contact data, but also force field and semiempirical calculations. Beside X-ray analysis, the absolute configuration of the P-stereogenic center was also determined on the basis of CD spectroscopy and high level quantum chemical calculations. The racemic and optically active 1-isopropyl-3-phospholenes obtained after deoxygenation were converted to the corresponding borane complexes and Pt(II) complexes.Stereostructure of the latter species was evaluated by high level quantum chemical calculations and the Pt complexes were tested as catalysts in the hydroformylation of styrene.

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“…Our research group synthesized a series of optically active 1‐aryl‐ and 1‐alkyl‐3‐methyl‐3‐phospholenes that were then converted to the corresponding platinum complexes, which were tested as catalysts in the hydroformylation of styrene. Enantiomeric excess (Ee‐s) up to 29% were obtained . The key step of the ligand synthesis is the optical resolution of the corresponding racemic phospholene oxides .…”

Section: Introductionmentioning

confidence: 99%