(±)-2,2'-бис(дифенилфосфино)-1,1'-винафтил

Химические свойства

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

Использование

1. 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.
2. It is also employed in palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines.
3. used with Cu(II) to catalyze the addition of arylsulfonamides to styrenes and olefins.

Реакции

Phosphine Ligand Kit component.

1. Useful ligand for palladium-catalyzed carbon-nitrogen bond formation.
2. Useful ligand for rhodium-catalyzed C-C bond formation.
3. Useful ligand for palladium-catalyzed intramolecular acylation of aryl bromides via C-H activation.
4. Used in the preparation of Buchwald third generation precatalyst.
5. Used in methoxy directed Rhodium migration.
6. Used in Nickel catalyzed C-N cross-coupling reactions.
   

Общее описание

Racemic version of BINAP.

Методы очистки

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.]