Editing BINAP (section)

==Use as ligand in asymmetric catalysis==
BINAP is used in [[organic synthesis]] for [[enantioselective]] transformations catalyzed by its [[complex (chemistry)|complexes]] of [[ruthenium]], [[rhodium]], and [[palladium]].<ref>{{cite journal |last=Kitamura |first=Masato |author2=M. Tokunaga |author3=T. Ohkuma |author4=R. Noyori  |year=1998 |title=Asymmetric hydrogenation of 3-oxo carboxylates using BINAP-ruthenium complexes |journal= [[Org. Synth.]] |volume=9 |pages=589 |url=http://www.orgsynth.org/orgsyn/prep.asp?prep=cv9p0589}}</ref> As pioneered by [[Ryōji Noyori]] and his co-workers, rhodium complexes of BINAP are useful for the synthesis of (–)-[[menthol]].<ref>{{cite journal |last=Akutagawa |first=S |year=1992 |title=A practical synthesis of (−)-menthol with the Rh-BINAP catalyst |journal= [[Chirality Ind.]] |pages=313–323}}</ref><ref>{{cite journal |last=Kumobayashi |first=Hidenori |author2=Sayo, Noboru |author3=Akutagawa, Susumu |author4=Sakaguchi, Toshiaki |author5= Tsuruta, Haruki  |year=1997 |title=Industrial asymmetric synthesis by use of metal-BINAP catalysts |journal= [[Nippon Kagaku Kaishi]] |volume=12 |issue=12 |pages=835–846|doi=10.1246/nikkashi.1997.835 |doi-access=free }}</ref>

[[Silver]] complexes are also important; BINAP-[[Silver(I) fluoride|AgF]] can be used to [[stereoselectivity|enantioselectively]] protonate [[silyl enol ether]]s.<ref>{{cite journal|last1=Yanagisawa|first1=Akira|last2=Touge|first2=Taichiro|last3=Takayoshi|first3=Arai|title=Enantioselective Protonation of Silyl Enolates Catalyzed by a Binap⋅AgF Complex|journal=Angewandte Chemie International Edition|date=2005|volume=44|issue=10|pages=1546–8|doi=10.1002/anie.200462325|pmid=15645475 }}</ref>

Subsequent studies revealed that related [[diphosphine]]s with a narrower dihedral angle between the aromatic faces give catalysts that are more enantioselective. One such ligand is [[SEGPHOS]].<ref>{{cite journal | vauthors=Shimizu H, Nagasaki I, Matsumura K, Sayo N, Saito T  | title = Developments in Asymmetric Hydrogenation from an Industrial Perspective | year = 2007 | journal = [[Acc. Chem. Res.]] | volume = 40 | issue = 12| pages = 1385–1393 | doi = 10.1021/ar700101x | pmid = 17685581}}</ref>