(S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl

Synthesis

Synthesis of 135139-00-3

Using phosphorus tribromide as a starting material, bis(3,5-dimethylphenyl)phosphine oxide was reacted with bis(3,5-dimethylphenyl)phosphine to obtain bis(3,5-dimethylphenyl)phosphine in 92% yield. Then, coupling was performed under Ni(dppe)Cl₂ as a catalyst and zinc powder as a reducing agent to yield (S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl.

Reaction

1. Ligand used in copper-catalyzed asymmetric Mannich-type reactions of N-acylimino esters.
2. Ligand used in the enantioselective fluorination of oxindoles.
3. Ligand used in [2+2+2] cycloaddition of tetraynes and hexaynes.
4. Ligand used in the asymmetric reduction of ketone via ruthenium-catalyzed transfer hydrogenation.
5. Asymmetric hydroboration of unsaturated imines.
    

Uses

Catalyst for:

• Asymmetric hydrogenation of benzophenone
• Regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives in the presence of chiral biaryl bisphosphine ligands
• Regiodivergent rhodium-catalyzed [(2+2)+2] carbocyclization of 1,6-enynes with Me propiolates
• Ligand controlled regioselective and stereoselective desymmetrizing rhodium-catalyzed allylic arylation of meso cyclopentene dicarbonates with arylboronic acids to form regioisomeric arylcyclopentenols
• Platinum(II) complex-catalyzed enantioselective aldol reaction with ketene silyl acetals in DMF at room temperature
• Stereoselective preparation of chiral N,O-biaryls via Rh-catalyzed [2+2+2] cycloaddition of conjugate ynamides with diynes