Abstract
A highly enantioselective rhodium-catalyzed addition of arylboronic acids to N -tosylarylimines is described, using chiral binaphtholic phosphite and phosphoramidite ligands. The best ee values (76-99%), associated with moderate to good chemical yields, were obtained with binaphtholic phosphoramidite ligands containing a bulky chiral amine.
Key words
arylations - arylboronic acids - asymmetric catalysis - imines - rhodium
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General Procedure for the Arylation of N
-Tosylaryl-imines : In a flame-dried Schlenk tube flushed with nitrogen, Rh(acac)(C2 H4 )2 (1.2 mg, 4.65 µmol, 3 mol%) and the ligand (9.30 µmol, 6 mol%) were dissolved in anhyd dioxane (0.75 mL). After stirring for 30 min at r.t., LiF (1.5 mmol) and the substrate (0.15 mmol) were added followed by the appropriate arylboronic acid (0.75 mmol). The resulting mixture was stirred at 50 °C for 24 h, quenched with H2 O (3 mL) and extracted with CH2 Cl2 (3 mL). The organic phase was dried over Na2 SO4 and the solvent was evaporated under vacuum. The residue was purified by flash chromatography on silica gel (n -hexane-EtOAc, 7:3) affording the N -tosyl-diarylmethylamine as a white solid.
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