76189-55-4 Usage
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.
Ligand for palladium-catalyzed enantioselective hetero Michael addition to form b-amino acid derivatives.
Ligand employed in rhodium-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols.
Ligand employed in rhodium-catalyzed 1,2-addition of aluminium organyl compounds to cyclic enones.
Ligand employed in iridium-catalyzed transfer hydrogenative allylation of benzylic alcohols.
Ligand employed in rhodium-catalyzed asymmetric C-Si bond formation by conjugate silyl transfer using a Si-B linkage.
Ligand employed in the iridium-catalyzed asymmetric cyclopropane-mediated carbonyl allylation of primary alcohols.
Ligand employed in the nickel-catalyzed asymmetric α-arylation of tetralones.
Ligand employed in the copper-catalyzed asymmetric propargylation of ketones.
Ligand employed in the cobalt-catalyzed asymmetric reductive coupling of alkynes with alkenes.
Ligand employed in the rhodium-catalyzed asymmetric 1,4-addition of arylalanes on trisubstituted enones.
Ruthenium-catalyzed asymmetric hydrocyanation of imines.
Palladium-catalyzed asymmetric intermolecular cyclization.
Chemical Properties
white to light yellow crystal powde
Uses
Different sources of media describe the Uses of 76189-55-4 differently. You can refer to the following data:
1. Chiral ligand for metal mediated asymmetric catalysis.
2. Useful ligand for transition metal catalyzed asymmetric reactions, including hydrogenation and disilylation. 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.Complex with Ag(I) used to catalyze an asymmetric aldol reaction between alkenyl trichloroacetates and aldehydes. Also used with Ag(I) to catalyze an enantioselective hetero-Diels-Alder reaction of azo compounds.
General Description
(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.
Check Digit Verification of cas no
The CAS Registry Mumber 76189-55-4 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 5 respectively.
Calculate Digit Verification of CAS Registry Number 76189-55:
(7*7)+(6*6)+(5*1)+(4*8)+(3*9)+(2*5)+(1*5)=164
164 % 10 = 4
So 76189-55-4 is a valid CAS Registry Number.
76189-55-4Relevant 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.
Metal-Free Reduction of Phosphine Oxides, Sulfoxides, and N-Oxides with Hydrosilanes using a Borinic Acid Precatalyst
Chardon, Aurélien,Maubert, Orianne,Rouden, Jacques,Blanchet, Jér?me
, p. 4460 - 4464 (2017/11/22)
The general reduction of phosphine oxides, sulfoxides, and amine N-oxides was achieved by combining bis(2-chlorophenyl)borinic acid with phenylsilane. The reaction was shown to tolerate a wide range of substrates and could be performed under mild conditions, with only 2.5 mol % of the easily synthesized catalyst. Mechanistic investigations pointed to a key borohydride as the real catalyst and at bis(2-chlorophenyl)borinic acid as a precatalyst.
