BINAP
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Through Ligand and Coordination complex
Use as ligand in asymmetric catalysis
BINAP is used in organic synthesis for enantioselective transformations catalyzed by its complexes of ruthenium, rhodium, and palladium. As pioneered by Ryōji Noyori and his co-workers, rhodium complexes of BINAP are useful for the synthesis of (–)-menthol.
Silver complexes are also important; BINAP-AgF can be used to enantioselectively protonate silyl enol ethers.
Subsequent studies revealed that related diphosphines with a narrower dihedral angle between the aromatic faces give catalysts that are more enantioselective. One such ligand is SEGPHOS.
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Preparation
BINAP is prepared from BINOL via its bistriflate derivatives. Both the (R)- and (S)-enantiomers, as well as the racemate, are commercially available. One of the wide applications include chemoselective hydrogenation, where BINAP is conjugated to rhodium.