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Chemical compound
BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) is an organophosphorus compound. This chiral diphosphine ligand is widely used in asymmetric synthesis
BINAP
Type of symmetry in molecules
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
Axial_chirality
Chemical reaction
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)
Asymmetric_hydrogenation
Use of metal-based Lewis acids to catalyze organic reactions
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
Lewis_acid_catalysis
Stereoisomerism due to hindered rotation
chirality). When the barrier to racemization is high, as illustrated by the BINAP ligands, the phenomenon becomes of practical value in asymmetric synthesis
Atropisomer
Chemical compound
dextrorotary one. BINOL is a precursor for another chiral ligand called BINAP. The volumetric mass density of the two enantiomers is 0.62 g cm−3.[citation
1,1′-Bi-2-naphthol
Chemical reaction
Ru(BINAP) catalyst. The configuration of the new stereocenter is predictable using the stereochemical model developed for hydrogenations employing BINAP
Enantioselective reduction of ketones
Enantioselective_reduction_of_ketones
Chemical compound
phosphine ligands such as 1,2-bis(diphenylphosphino)ethane (Ph2PCH2CH2PPh2) and BINAP via their respective bistriflate derivatives. Both the (R)- and (S)-enantiomers
Diphenylphosphine
Japanese chemist (born 1938)
particularly those based on the BINAP ligand. Asymmetric hydrogenation of an alkene in the presence of ((S)-BINAP)Ru(OAc)2 is used for the commercial
Ryōji_Noyori
Type of chemical bonding with metal ions
catalysts are often chelated complexes. A representative example is the use of BINAP (a bidentate phosphine) in Noyori asymmetric hydrogenation and asymmetric
Chelation
Chemical compound
to 1,1-binaphthol: Such compounds are intermediates in the synthesis of BINAP and its derivatives. Copper(II) chloride dihydrate promotes the hydrolysis
Copper(II)_chloride
Monoterpenoid and alcohol that is the primary component of citronella oil
Noyori, Ryoji (1995). "Asymmetric Hydrogenation of Allylic Alcohols Using BINAP–Ruthenium Complexes: (S)-(−)-citronellol". Organic Syntheses. 72: 74. doi:10
Geraniol
Method of separating enantiomers in a racemic mixture by reaction rate
allylic alcohols by asymmetric hydrogenation of the olefin. Utilizing the Ru[BINAP] complex, selective hydrogenation can give high ee's of the unsaturated
Kinetic_resolution
Chemistry
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
Dynamic kinetic resolution in asymmetric synthesis
Dynamic_kinetic_resolution_in_asymmetric_synthesis
Organic compound used as flavouring and analgesic
myrcene, which undergoes asymmetric isomerisation in the presence of a BINAP rhodium complex to give (after hydrolysis) enantiomerically pure R-citronellal
Menthol
Carboxylic acid
be obtained by asymmetric hydrogenation of tiglic acid using a ruthenium-BINAP catalyst. The compound and its enantiomers react as typical carboxylic acids:
2-Methylbutanoic_acid
Process of increasing the rate of a chemical reaction
synthesized efficiently from hydroxyacetone by using catalysts based on BINAP-ruthenium complexes, in Noyori asymmetric hydrogenation: One of the most
Catalysis
Addition of non-molecular hydrogen to a compound
of ketones was demonstrated with ruthenium-based complexes of BINAP. Even though the BINAP-Ru dihalide catalyst could reduce functionalized ketones, the
Transfer_hydrogenation
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Coupling reaction
palladium(II) acetate. Typical supporting ligands are triphenylphosphine, PHOX, and BINAP. Typical bases are triethylamine, potassium carbonate, and sodium acetate
Heck_reaction
Chemical compound
polymethylhydrosiloxane, palladium(II) acetate, potassium phosphate and the DPDB ligand (BINAP) Another synthesis route starts by treating pyridinium or pyrylium salts
Azulene
Chemical reaction(s) which favor one chiral isomer over another
example, Noyori asymmetric hydrogenation with BINAP/Ru requires a β-ketone, although another catalyst, BINAP/diamine-Ru, widens the scope to α,β-alkenes
Enantioselective_synthesis
Chemical compound
optically stable. Some derivatives, as well as related molecules such as BINAP, find application as ligands in asymmetric synthesis. In the case of unsubstituted
Biphenyl
Chemical compound
Corporation that is used in asymmetric synthesis. It was developed after BINAP and was investigated since it has a narrower dihedral angle between the
SEGPHOS
Chemical compound
(1999). "(R)-(+)- and (S)-(−)-2,2'-Bis(Diphenylphosphino)-1,1'-Binaphthyl (BINAP)". Organic Syntheses. 76: 6. doi:10.15227/orgsyn.076.0006. Dell'Amico, Daniela
Trifluoromethanesulfonic anhydride
Trifluoromethanesulfonic_anhydride
Chemical element with atomic number 45 (Rh)
Rhodium(I) complexes are commonly used as catalysis, with a few being BINAP-Rh(I), DIPAMP-Rh(I), and BDPP-Rh(I). Cyclopentadienyl complexes of rhodium
Rhodium
River in Nepal
tributaries of this river are Sapanatirtha Khola, Sangle Khola, Lhora Khola, and Binap Falls. Bisnap[clarification needed] fall locates at the Shivapuri National
Bisnumati_River
Chemical compound
reaction: Another organic synthetic method using silver(I) fluoride is the BINAP-AgF complex catalyzed enantioselective protonation of silyl enol ethers:
Silver(I)_fluoride
Chemical compound
in 93% yield. The asymmetric hydrogenation of diketene with a ruthenium BINAP catalyst to optically active (R)-β-butyrolactone with 97% selectivity and
Β-Butyrolactone
Class of chemical substance
zirconium phosphonate-derived Ru-BINAP systems. Zirconium phosphonate-based chiral porous hybrid materials containing the Ru(BINAP)(diamine)Cl2 precatalysts
Metal–organic_framework
4-bis(diphenylphosphino)butane) Chiraphos 2,3-Bis(diphenylphosphino)butane BINAP 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 93 Xantphos 4,5-Bis(diphenylphosphino)-9
Diphosphine_ligands
Chemical reaction
and Fe catalysts, which have had a large impact on the development of BINAP-type ligands used asymmetric catalysis. Lignin, a polyphenol that is found
Oxidative_coupling_of_phenols
bidentate phosphine ligands can also be useful in organoruthenium compounds. BINAP, in particular, is a useful asymmetric ligand for many asymmetric ruthenium
Organoruthenium_chemistry
Chemical compound
Kiyomi (October 22, 2005). "Facile Preparation of a New BINAP-Based Building Block, 5,5'-DiiodoBINAP, and Its Synthetic Application". The Journal of Organic
Cyclopentyl_methyl_ether
Chemical reaction for synthesizing C–N bonds
albeit with modest yields. The development of diphenylphosphinobinapthyl (BINAP) and diphenylphosphinoferrocene (DPPF) as ligands for the Buchwald–Hartwig
Buchwald–Hartwig_amination
Chemical reaction
palladium The ligand L in the catalyst can be triphenylphosphine, dppe, BINAP, chiraphos or XPhos. Palladium catalysts in general have higher chemical
Negishi_coupling
Methods for determining rate laws of chemical reactions and to elucidate their mechanisms
"Reevaluation of the Mechanism of the Amination of Aryl Halides Catalyzed by BINAP-Ligated Palladium Complexes". J. Am. Chem. Soc. 128 (11): 3584–3591. Bibcode:2006JAChS
Reaction progress kinetic analysis
Reaction_progress_kinetic_analysis
Indian scientist
yields and excellent enantioselectivities using Cu-Al hydrotalcite and BINAP has opened up a new perspective. Innovative design of catalysts for the
Lakshmi_Kantam
where they have been shown to be superior to more common ligands such as BINAP. In asymmetric hydrogenation iridium complexes of phosphinooxazolines catalyse
Phosphinooxazolines
Phosphorus-containing ligands
Pd-catalyzed C-N bond-forming cross-coupling (e.g., tris(o-tolyl)phosphine and BINAP, respectively) necessitated harsh conditions, and the scope of the transformation
Dialkylbiaryl phosphine ligands
Dialkylbiaryl_phosphine_ligands
Government agency of Victoria, Australia
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Victorian_School_Building_Authority
achiral borane source is more common, e.g. chiral diphosphines such as BINAP. Styrene or its simple derivatives are usually the prochiral substrate.
Metal-catalysed_hydroboration
Organic reaction between a silyl enol ether and an aldehyde or formate
enolates: Enantioselective dienolate additions to aldehydes mediated by Tol-BINAP center Cu(II) fluoride complexes". Journal of the American Chemical Society
Mukaiyama_aldol_addition
Ligands that lack mirror symmetry but have two-fold rotational symmetry
bis(oxazoline) ligands are used in organic synthesis Both enantiomers of BINAP BINOL, another binaphthalene-based ligand TADDOL DIPAMP, a diphosphine of
C2-Symmetric_ligands
Chemical reaction
auxiliaries can make the reaction enantioselective (see § Amine N-oxides). BINAP is commonly employed. Typical Pauson-Khand conditions are elevated temperatures
Pauson–Khand_reaction
Chemical process
the palladium(0) complex in the presence of chiral diphosphine ligand (S)-binap yields chiral palladium(II) complex 77. This step is followed by the dissociation
Cascade_reaction
Chemical compound
phosphines are C2-symmetric diphosphines. Famous examples are DIPAMP and BINAP. These chelating ligands support catalysts used in asymmetric hydrogenation
P-Chiral_phosphine
Organic reaction
cyclohexenone, phenylboronic acid, a rhodium acac catalyst and the chiral ligand BINAP.[2] In another example of asymmetric synthesis the α,β-unsaturated carbonyl
Nucleophilic conjugate addition
Nucleophilic_conjugate_addition
Organic reduction of any carbonyl group by a reducing agent
synthesis are the Noyori asymmetric hydrogenation (beta-ketoester reduction/Ru/BINAP) and the CBS reduction (BH3, proline derived chiral catalyst). The Bouveault–Blanc
Carbonyl_reduction
Chemical compound
enantioselective (80 to 92% ee) reduction of prochiral α,β-unsaturated esters uses Tol-BINAP complexes of copper in the presence of PMHS as the reductant. Subsequently
Copper_hydride
Chemical reaction to produce organic compounds
(9) Asymmetric IMHR may establish tertiary or quaternary stereocenters. BINAP is the most commonly chiral ligand used in this context. An interesting
Intramolecular_Heck_reaction
Family of chiral diphosphine ligands used for asymmetric catalysis
the above reaction has e.e.'s up to 92% and TOF of 5-10 h−1. Hayashi's Rh-binap complex gives better yield. Hydroformylation of Styrene This reaction scheme
Josiphos_ligands
Pure chemical substances produced by and for the chemical industry
synthesis using chiral catalysts. Among the latter, enzymes and synthetic BINAP (2,2'–Bis(diphenylphosphino)–1,1'–binaphthyl) types are used most frequently
Fine_chemical
Principle in chemical kinetics
stereoselective hydrogenation of 2-substituted 3-oxo carboxylic esters catalyzed by BINAP-ruthenium(II) complexes". Journal of the American Chemical Society. 115
Curtin–Hammett_principle
Typer of isomerization
access to asymmetric 7– and 8–membered carbocycles is possible using chiral BINAP Au(I) gold catalyst, giving a wide variety of products. It is proposed that
Cycloisomerization
using rhodium or ruthenium phosphine catalysts, such as Noyori's Ru(II)-BINAP complexes, which require the presence of a free carboxy, amide, or hydroxy
Semicorrin
Nucleophilic addition of an allyl, allenyl or propargyl-stannane
(acyloxy)borane or "CAB" catalyst 1, titanium-BINOL system 2, and silver-BINAP system 3 provide addition products in high ee via the Lewis-acid-promoted
Organostannane_addition
Nanoparticle catalysts
produces metal nanoparticle that catalyze the hydrosilylation reaction. BINAP-functionalized palladium nanoparticles and gold nanoparticles have been
Nanomaterial-based_catalyst
ligands as the spectator ligands. Many of these diphosphine ligands, such as BINAP, contain arene rings and impart chirality from atropisomerism; the rigidity
Metal-ligand_cooperativity
Japanese Chemist
bidentate bisphosphoramidite (Me-BIPAM) through the addition of a rhodium(I)-binap catalyst into an enantioselective 1,4-addition of aryl- and 1-alkenylboronic
Norio_Miyaura
enantioselective versions of the Crabbé reaction in which chiral PINAP (aza-BINAP) based ligands for copper are employed. The stepwise application of copper
Crabbé_reaction
American chemist
phosphines can be used for asymmetric catalysis, including DIPAMP, DIOP and BINAP. These phosphines include stereogenic phosphorus centres, axial chirality
Ohyun_Kwon
Chemical process
conjunction with azo compounds, enantioselectivity is observed (see above). BINAP can also be used for this purpose in the amination of silyl enol ethers
Electrophilic_amination
Chemical reaction
version of the reaction was reported by Wender et al in 2005, featuring a Rh-BINAP catalyst that induces up to >99% enantiomeric excess. Yu and co-workers
Vinylcyclopropane (5+2) cycloaddition
Vinylcyclopropane_(5+2)_cycloaddition
BINAP
BINAP
BINAP
BINAP
Boy/Male
Hindu
Power and well being in the future, Cool
Male
English
Variant spelling of English Hugh, HUE means "heart," "mind," or "spirit."
Surname or Lastname
Dutch and Belgian
Dutch and Belgian : variant of Haas. Debrabandere notes that in Flanders this is found as a shortened form of Hazaert (see Hazard).English and Irish : variant spelling of Hayes or Hays.
Boy/Male
Afghan, Armenian, Australian
Protector
Girl/Female
Maori
Beloved child.
Girl/Female
Indian, Punjabi, Sikh
Mighty and Brave
Boy/Male
American, Australian, Dutch, French, Irish, Jamaican
Night Time; Nut Tree; From the Elder Tree Grove
Surname or Lastname
English
English : unexplained.
Boy/Male
Hindu, Indian, Marathi
Very Gracious
Boy/Male
Tamil
Pre eminent
BINAP
BINAP
BINAP
BINAP
BINAP