Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Ball and stick model of BINAP viewed as above
BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) is an organophosphorus compound. This chiral diphosphine ligand is widely used in asymmetric synthesis. It consists of a pair of 2-diphenylphosphinonaphthyl groups linked at the 1 and 1′ positions. This C2-symmetric framework lacks a stereogenic atom, but has axial chirality due to restricted rotation (atropisomerism). The barrier to racemization is high due to steric hindrance, which limits rotation about the bond linking the naphthyl rings. The dihedral angle between the naphthyl groups is approximately 90°. The natural bite angle is 93°.[1]
^Birkholz (née Gensow), Mandy-Nicole; Freixa, Zoraida; van Leeuwen, Piet W. N. M. (2009). "Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions". Chemical Society Reviews. 38 (4): 1099–1118. doi:10.1039/B806211K. PMID 19421583.
BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) is an organophosphorus compound. This chiral diphosphine ligand is widely used in asymmetric synthesis...
steric hindrance of the groups, as in substituted biaryl compounds such as BINAP, or by torsional stiffness of the bonds, as in the C=C double bonds in allenes...
chirality). When the barrier to racemization is high, as illustrated by the BINAP ligands, the phenomenon becomes of practical value in asymmetric synthesis...
backbone. BINAP chelates onto a metal (usually a late transition metal) to form a C2-symmetric complex. As shown below in the structure of an (R)-BINAP ruthenium...
the BINAP-Ru-diamine system. The dihalide form of the catalyst is converted to the catalysts by reaction of H2 in the presence of base: RuCl2(BINAP)(diamine)...
phosphine ligands such as 1,2-bis(diphenylphosphino)ethane (Ph2PC2H4PPh2) and BINAP. via its bistriflate derivatives. Both the (R)- and (S)-enantiomers, as...
used to reduce benzene to cyclohexane. The complex of a rhodium ion with BINAP is a widely used chiral catalyst for chiral synthesis, as in the synthesis...
myrcene, which undergoes asymmetric isomerisation in the presence of a BINAP rhodium complex to give (after hydrolysis) enantiomerically pure R-citronellal...
basic conditions. To select for one of the four possible stereoisomers, a BINAP-Ru catalyst is used to control the outcome of the reaction through the steric...
allylic alcohols by asymmetric hydrogenation of the olefin. Utilizing the Ru[BINAP] complex, selective hydrogenation can give high ee's of the unsaturated...
catalysts are often chelated complexes. A representative example is the use of BINAP (a bidentate phosphine) in Noyori asymmetric hydrogenation and asymmetric...
Ru(BINAP) catalyst. The configuration of the new stereocenter is predictable using the stereochemical model developed for hydrogenations employing BINAP...
synthesized efficiently from hydroxyacetone by using catalysts based on BINAP-ruthenium complexes, in Noyori asymmetric hydrogenation: One of the most...
of ketones was demonstrated with ruthenium-based complexes of BINAP. Even though the BINAP-Ru dihalide catalyst could reduce functionalized ketones, the...
optically stable. Some derivatives, as well as related molecules such as BINAP, find application as ligands in asymmetric synthesis. In the case of unsubstituted...
example, Noyori asymmetric hydrogenation with BINAP/Ru requires a β-ketone, although another catalyst, BINAP/diamine-Ru, widens the scope to α,β-alkenes...
palladium(II) acetate. Typical supporting ligands are triphenylphosphine, PHOX, and BINAP. Typical bases are triethylamine, potassium carbonate, and sodium acetate...
palladium The ligand L in the catalyst can be triphenylphosphine, dppe, BINAP, chiraphos or XPhos. Palladium catalysts in general have higher chemical...
tributaries of this river are Sapanatirtha Khola, Sangle Khola, Lhora Khola, and Binap Falls. Bisnap[clarification needed] fall locates at the Shivapuri National...
Kiyomi (October 22, 2005). "Facile Preparation of a New BINAP-Based Building Block, 5,5'-DiiodoBINAP, and Its Synthetic Application". The Journal of Organic...
Corporation that is used in asymmetric synthesis. It was developed after BINAP and was investigated since it has a narrower dihedral angle between the...
enolates: Enantioselective dienolate additions to aldehydes mediated by Tol-BINAP center Cu(II) fluoride complexes". Journal of the American Chemical Society...
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