76189-56-5 Usage
Description
(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, commonly known as BINAP, is a chiral ligand that plays a crucial role in various chemical reactions due to its unique structure. It is a white to light yellow crystalline powder and is widely used in the field of asymmetric catalysis.
Uses
Used in Enantioselective and Diasteroselective Reactions:
BINAP is used as a ligand in enantioselective and diastereoselective unpoled carbonyl allylation reactions. Its chiral structure allows for the selective formation of desired enantiomers or diastereomers, which is essential in the synthesis of complex organic molecules.
Used in the Synthesis of Organophosphine Oxides:
BINAP is utilized as a ligand in the synthesis of organophosphine oxides, which are potential antitumor agents. Its unique structure contributes to the selectivity and efficiency of the reaction, leading to the production of the desired organophosphine oxides.
Used in SN2 Halogenation of Hydroxy Groups:
BINAP serves as a ligand in the SN2 halogenation of hydroxy groups, a reaction that is important in the synthesis of various organic compounds. Its presence enhances the selectivity and efficiency of the reaction, resulting in the desired halogenated products.
Used in the Synthesis of BINAP Complexes:
BINAP is used in the synthesis of its own metal complexes, such as rhodium and ruthenium derivatives. These complexes are highly selective homogeneous catalysts for various reactions, including the reduction of aryl ketones, β-keto esters, and α-amino ketones.
Used in Asymmetric Hydrogenation and Hydroformylation of Olefins:
BINAP and its metal complexes are employed as catalysts in asymmetric hydrogenation and hydroformylation of olefins. These reactions are crucial in the production of chiral compounds, which are essential in the pharmaceutical and agrochemical industries.
Used in Asymmetric Heck Reactions:
BINAP is used as a ligand in asymmetric Heck reactions, which are important in the synthesis of complex organic molecules with high enantioselectivity. Its chiral structure allows for the selective formation of desired products, making it a valuable tool in organic synthesis.
Used in Asymmetric Isomerizations of Allyls:
BINAP is utilized as a ligand in asymmetric isomerizations of allyl compounds. These reactions are essential in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Used in Palladium-Catalyzed, Asymmetric, Tandem Heck Reaction-Carbanion Capture Process:
BINAP is used as a ligand in a palladium-catalyzed, asymmetric, tandem Heck reaction-carbanion capture process, which leads to the synthesis of a tricyclic sesquiterpene. This process is important in the production of complex organic molecules with high enantioselectivity.
Used in Ruthenium-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Acids:
BINAP is employed as a ligand in a ruthenium-catalyzed asymmetric hydrogenation of α,β-unsaturated acids. This reaction is crucial in the synthesis of chiral compounds, which are essential in various industries, including pharmaceuticals and agrochemicals.
Used in Studies of Conformational Flexibility of BINAP Chelates:
BINAP is used in research to study the conformational flexibility of its metal chelates. Understanding the conformational behavior of these chelates is essential for optimizing their performance in various catalytic reactions.
Reaction
(R)-BINAP or (R)-Tol-BINAP can be combined with dichloro(1,5-cyclooctadiene)ruthenium to form precursors to NOYORI CATALYST SYSTEMS. These systems exhibit very high catalytic activity and enantioselectivity in the hydrogenation of a wide range of substrates. NOYORI CATALYST SYSTEMS have been shown to effect highly enantioselective hydrogenation of functionalized ketones where the substituents are dialkylamino, hydroxy, siloxy, carbonyl, ester, amide or thioester.
Useful ligand in asymmetric Heck processes.
Ligand employed in palladium-catalyzed asymmetric arylation of ketones.
Ligand employed in rhodium-catalyzed 1,4-additions to enones.
Ligand employed in palladium-catalyzed hydroamination of styrene derivatives.
Ligand employed in silver-catalyzed asymmetric Sakuri-Hosomi allylation and Mukaiyama aldol reaction.
Ligand employed in rhodium-catalyzed kinetic resolution of enynes.
Ligand employed in asymmetric rhodium-catalyzed hydroboration of cyclopropenes.
Ligand employed in silver-catalyzed a-hydroxylation of stannyl enol ethers.
Ligand employed in palladium-catalyzed synthesis of chiral allenes.
Check Digit Verification of cas no
The CAS Registry Mumber 76189-56-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,6,1,8 and 9 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 76189-56:
(7*7)+(6*6)+(5*1)+(4*8)+(3*9)+(2*5)+(1*6)=165
165 % 10 = 5
So 76189-56-5 is a valid CAS Registry Number.
76189-56-5Relevant articles and documents
The Trityl-Cation Mediated Phosphine Oxides Reduction
Landais, Yannick,Laye, Claire,Lusseau, Jonathan,Robert, Frédéric
supporting information, p. 3035 - 3043 (2021/05/10)
Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).
Synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene
-
, (2020/09/12)
The invention relates to a synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene, which is realized by the following steps: step 1, carrying out BUCHERER reaction on 1, 1 '-binaphthyl-2-naphthol to generate 1, 1'-binaphthyl-2, 2 '-diamine; 2, subjecting 1, 1 '-binaphthyl-2, 2'-diamine to a Sandmeyer reaction to generate binaphthyl dibromide; and 3, carrying out a Grignard reaction onthe binaphthyl dibromide and diphenyl phosphine chloride to generate 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene (BINAP). Bulk chemical raw materials are used and are low in price and easy to obtain, and the production cost is effectively reduced; the method has the advantages of easily available raw materials, high reaction yield, simple post-treatment, facilitation of industrial amplification, and strong industrial application prospect.
Chemoselective Reduction of Phosphine Oxides by 1,3-Diphenyl-Disiloxane
Buonomo, Joseph A.,Eiden, Carter G.,Aldrich, Courtney C.
supporting information, p. 14434 - 14438 (2017/10/23)
Reduction of phosphine oxides to the corresponding phosphines represents the most straightforward method to prepare these valuable reagents. However, existing methods to reduce phosphine oxides suffer from inadequate chemoselectivity due to the strength of the P=O bond and/or poor atom economy. Herein, we report the discovery of the most powerful chemoselective reductant for this transformation to date, 1,3-diphenyl-disiloxane (DPDS). Additive-free DPDS selectively reduces both secondary and tertiary phosphine oxides with retention of configuration even in the presence of aldehyde, nitro, ester, α,β-unsaturated carbonyls, azocarboxylates, and cyano functional groups. Arrhenius analysis indicates that the activation barrier for reduction by DPDS is significantly lower than any previously calculated silane reduction system. Inclusion of a catalytic Br?nsted acid further reduced the activation barrier and led to the first silane-mediated reduction of acyclic phosphine oxides at room temperature.
