76189-56-5 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.
Chemical Properties
white to light yellow crystal powde
Uses
Different sources of media describe the Uses of 76189-56-5 differently. You can refer to the following data:
1. Reactant involved in:Enantioselective and diastereoselective unpoled carbonyl allylationSyntehsis of organophophine oxides as anittumor agentsSN2 halogenation of hydroxy groupsSynthesis of BINAP complexesStudies of conformational flexibility of BINAP chelates
2. 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.Ligand used in a palladium-catalyzed, asymmetric, tandem Heck reaction-carbanion capture process leading to a synthesis of a tricyclic sesquiterpene. Also used in a ruthenium-catalyzed asymmetric hydrogenation of α,β-unsaturated acids.
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
One-pot synthesis of binaphthyl-based phosphines via direct modification of BINAP
Ye, Jing-Jing,Zhang, Jian-Qiu,Shimada, Shigeru,Han, Li-Biao
supporting information, (2021/11/18)
Herein reported is the convenient and efficient strategy for the preparation of binaphthyl-based phosphines through direct modification to the commercially available 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) with sodium. In the absence of 15-crown-5-ether, a cyclic sodium dinapthylphospholide intermediate is mainly generated. With 15-crown-5-ether, P-Ph bonds are selectively cleft by Na to produce binaphthyl-based disodium phosphides. The mechanism of selective formation of sodium dinapthylphospholide or binaphthyl-based disodium phosphides is proposed.
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.
