- Phosphination of Phenol Derivatives and Applications to Divergent Synthesis of Phosphine Ligands
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We describe a general and efficient protocol for the synthesis of organophosphine compounds from phenols and phosphines (R2PH) via a metal-free C-O bond cleavage and C-P bond formation process. This approach exhibits broad substrate scope and excellent functional group tolerance. The synthetic utilities of this protocol were demonstrated by the synthesis of chiral ligands via the various transformations of cyano groups and their applications in asymmetric catalysis.
- Li, Chenchen,Zhang, Kezhuo,Zhang, Minghao,Zhang, Wu,Zhao, Wanxiang
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supporting information
p. 8766 - 8771
(2021/11/20)
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- Highly efficient synthesis of (Phosphinodihydrooxazole)- (1,5-cyclooctadiene) Iridium complexes
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A highly efficient one-pot procedure for the synthesis of complexes of the type [Ir(COD)(Phox)]X, where Phox is a (chiral) phosphinooxazoline ligand, X = PF6 or B[(3,5-(CF3)2C6H 3)]4 (BARF), is developed. Former reported syntheses demanded the isolation of pure ligands by column chromatography, but the ligands tend to adsorb irreversibly on silica. Moreover, the chromatography has to be performed with careful exclusion of air. The present method avoids this difficulties. The yields of the syntheses are comparable with those starting from the pure ligands. The method is also suitable for the preparation of complexes of the type [Rh(COD)(Phox)]BARF and [Rh(Phox)2]BARF.
- Semeniuchenko, Volodymyr,Khilya, Volodymyr,Groth, Ulrich
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experimental part
p. 1147 - 1158
(2010/03/02)
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- Preparation of chiral phosphorus, sulfur and selenium containing 2-aryloxazolines
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A series of enantiomerically pure 2-[2-(diarylphosphino)aryl]-oxazolines was prepared from commercially available or synthetic amino alcohols. For oxazoline formation three procedures were employed: (i) one pot condensation with a 2-halobenzoic acid (ii) ZnCl2 catalyzed condensation with a 2-halobenzonitrile, and (iii) a three step sequence via a 2-halobenzamide and a tosylate or chloride. Phosphinooxazolines containing stereogenic phosphorous were prepared by either diastereoselective nucleophilic substitution of halogenide of Ar1Ar2PCl or by nucleophilic aromatic substitution with LiPAr1Ar2. In addition, sulfur and selenium analogs were prepared.
- Peer, Markus,De Jong, Johannes C.,Kiefer, Matthias,Langer, Thomas,Rieck, Heiko,Schell, Heico,Sennhenn, Peter,Sprinz, Juergen,Steinhagen, Henning,Wiese, Burkhard,Helmchen, Guenter
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p. 7547 - 7583
(2007/10/03)
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- Synthesis of chiral (phosphinoaryl)oxazolines, a versatile class of ligands for asymmetric catalysis
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Enantiomerically pure 2-oxazolines are readily prepared from 2-bromobenzonitrile by transmetalation with BuLi, subsequent reaction with chlorodiphenylphosphine and conversion of the resulting phosphinoaryl nitrile to the oxazoli
- Koch, Guido,Lloyd-Jones, Guy C.,Loiseleur, Olivier,Pfaltz, Andreas,Pretot, Roger,et al.
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p. 206 - 210
(2007/10/02)
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- Preparation of Novel Sulfur and Phosphorus Containing Oxazolines as Ligands for Asymmetric Catalysis
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The preparation of enantiomerically pure ligands which contain both an oxazoline group and an additional sulfur or phosphorus donor atom are described.Methylthiomethyl, o-thioanisyl and thienyl oxazolines have been prepared in one step, and o-diphenylphosphinophenyl oxazolines have been prepared in two steps in good yields from commercially available starting materials.
- Allen, Joanne V.,Dawson, Graham J.,Frost, Christopher G.,Williams, Jonathan M. J.,Coote, Steven J.
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p. 799 - 808
(2007/10/02)
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- Palladium-catalysed Asymmetric Allylic Substitution: a Ligand Design Incorporating Steric and Electronic Effects
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Enantiomerically pure ligands containing a 4,5-dihydrooxazole moiety tethered to an auxiliary sulfur or phosphorus donor have been prepared.These ligands have been exploited for palladium-catalysed asymmetric allylic substitution, providing enantioselectivity in the catalytic reaction is discussed in terms of the steric and electronic influences provided by the ligand.
- Allen, Joanne V.,Coote, Steven J.,Dawson, Graham J.,Frost, Christopher G.,Martin, Christopher J.,Williams, Jonathon, M.
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p. 2065 - 2072
(2007/10/02)
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- Phosphinoaryl- and phosphinoalkyloxazolines as new chiral ligands for enantioselective catalysis: Very high enantioselectivity in palladium catalyzed allylic substitutions
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Chiral phosphinoaryl- and phosphinoalkyloxazolines, a new class of chelate ligands, were prepared via convenient routes. Palladium complexes of the new ligands have proved to be highly effective catalysts for allylic substitution reactions. Enantioselectivity of up to 98.5% ee in the reaction of dimethyl malonate with 1,3-diphenyl-2-propenyl acetate is the highest so far achieved in this area.
- Sprinz,Helmchen
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p. 1769 - 1772
(2007/10/02)
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- Asymmetric Palladium Catalysed Allylic Substitution Using Phosphorus Containing Oxazoline Ligands
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A series of new phosphorus-containing oxazoline ligands has been developed.The use of these ligands for asymmetric palladium catalysed allylic substitution of 1,3-diphenylprop-2-enyl-1-acetate 12 with the sodium salt of dimethylmalonate has been achieved
- Dawson, Graham J.,Frost, Christopher G.,Williams, Jonathan M. J.,Coote, Steven J.
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p. 3149 - 3150
(2007/10/02)
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