In an article, author is Chrzanowski, Jacek, once mentioned the application of 18437-78-0, Quality Control of Tris(4-fluorophenyl)phosphine, Name is Tris(4-fluorophenyl)phosphine, molecular formula is C18H12F3P, molecular weight is 316.26, MDL number is MFCD00013553, category is chiral-phosphine-ligands. Now introduce a scientific discovery about this category.
Synthesis of Enantioenriched Aryl-tert-Butylphenylphosphine Oxides via Cross-Coupling Reactions of tert-Butylphenylphosphine Oxide with Aryl Halides
A series of enantiomerically enriched tertiary phosphine oxides have been prepared via the Pd-catalyzed cross-coupling reactions of enantiomerically pure tert-butylphenylphosphine oxide, with a variety of aryl iodides and bromides. This new protocol under optimized reaction conditions [toluene, 110 C-0, Pd(PPh3)(4), K2CO3 (or Et3N)] afforded highly functionalized P-chiral phosphine oxides with a yield of 78% to 95% and with enantiomeric excesses above 98%. The stereoretentive outcome of the cross-coupling reactions was proved by X-ray crystallography of selected phosphine oxides: (S)-(2-aminophenyl)(tert-butyl)(phenyl)phosphine oxide (3a) and (S)-anthracen-9-yl(tert-butyl)(phenyl)phosphine oxide (3i). When attempting to convert the enantiomerically pure phosphine oxide 3a to the corresponding borane by the treatment with the borane dimethyl sulfide complex partial stereoerosion at a stereogenic phosphorus atom was observed. Racemic tert-butyl (2-(dimethylamino)phenyl)(phenyl)phosphine (7a) was isolated in a quantitative yield upon deprotection of the corresponding borane (8a) and converted to a palladium crystalline complex (9), the structure of which has been proved by X-ray crystallography.
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Reference:
Phosphine ligand,
,Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate