98327-87-8

Chemical Properties

1.1'-Binaphthyl-2.2'-diphemyl phosphine is White to light beige powder

Uses

racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl ( (+/-)-BINAP ) is an essential role in the organic synthesis of enantioselective transformations catalyzed by the complexes of ruthenium, rhodium and palladium. It is also employed in palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines. used with Cu(II) to catalyze the addition of arylsulfonamides to styrenes and olefins.

Reactions

Phosphine Ligand Kit component. Useful ligand for palladium-catalyzed carbon-nitrogen bond formation. Useful ligand for rhodium-catalyzed C-C bond formation. Useful ligand for palladium-catalyzed intramolecular acylation of aryl bromides via C-H activation. Used in the preparation of Buchwald third generation precatalyst. Used in methoxy directed Rhodium migration. Used in Nickel catalyzed C-N cross-coupling reactions.

General Description

Racemic version of BINAP.

Purification Methods

Dissolve the enantiomer in toluene, wash it with 30% aqueous NaOH, three times with H2O, dry (Na2SO4), evaporate to ~15% of its volume and add an equal volume of degassed MeOH. Collect the solid, wash it with MeOH and dry it at 80o/0.005mm for 6hours. Recrystallise it from a 1:1 mixture of toluene/EtOH to optical purity (m 241-242o) [Takaya et al. Org Synth 67 20 1989]. [Noyori & Takaya Acc Chem Res 2 3 345 1990, Kitamura et al. Org Synth 71 1 1993, Takaya et al. Org Synth 72 74 1995, Kitamura et al. J Org Chem 57 4053 1992.]