149245-03-4

Usage

Uses

Used in Organometallic Chemistry:
(RS)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline is used as a ligand for forming coordination complexes with metal atoms. (RS)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline's structure allows for versatile bonding options, enhancing the stability and reactivity of the resulting complexes.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, (RS)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline is used as a catalyst in the synthesis of various drugs. The coordination complexes formed with metal atoms facilitate chemical reactions that are essential for producing pharmaceutical compounds.
Used in Fine Chemicals Production:
(RS)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline also finds application in the production of fine chemicals, which are high-purity chemicals used in various industries, such as electronics, agriculture, and fragrances. (RS)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline's role as a catalyst in these processes helps to improve the efficiency and selectivity of the chemical reactions involved.
Used in Industrial Processes:
The structure and properties of (RS)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline make it a valuable compound for use in various industrial processes. Its ability to form coordination complexes with metal atoms can lead to improved catalysts and more efficient chemical reactions, ultimately benefiting the overall production process.

InChI:InChI=1/C31H22NP/c1-3-13-25(14-4-1)33(26-15-5-2-6-16-26)29-20-19-23-11-7-9-17-27(23)30(29)31-28-18-10-8-12-24(28)21-22-32-31/h1-22H

Upstream product

• 149245-07-8 (1-(isoquinolin-1-yl)naphthalen-2-yl)diphenylphosphine oxide 
• 1079-66-9 chloro-diphenylphosphine 
• 149245-06-7 1-(2-trifluoromethanesulfonyloxy-1-naphthyl)isoquinoline 
• 1000062-70-3 1-(2-bromonaphthalen-1-yl)isoquinoline 
• 829-85-6 diphenylphosphane 
• 93-04-9 2-Methoxynaphthalene 
• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 104116-17-8 2-methoxynaphthalene-1-boronic acid 
• 17154-34-6 (trimethylsilyl)diphenylphosphine 
• 773-90-0 1-diazo-2(1H)naphthalenone 
• 54879-88-8 N-benzyl-2,2-dimethoxyethylamine 
• 100-52-7 benzaldehyde 
• 119-65-3 isoquinoline 
• 135-19-3 β-naphthol 

Downstream Products

• 452303-25-2 [1-(2-diphenylphosphino-1-naphthyl)isoquinoline]tricarbonylrhenium(I) chloride 
• 1108697-63-7 [Cu(1-(2-diphenylphosphini-1-naphthyl)isoquinoline)I]2 
• 149245-07-8 (1-(isoquinolin-1-yl)naphthalen-2-yl)diphenylphosphine oxide 
• 155411-27-1 Rh((C₆H₅)2P(C₁₉H₁₂N))2⁽¹⁺⁾*CF₃SO₃^(1-)={Rh((C₆H₅)2P(C₁₉H₁₂N))2}CF₃SO₃ 
• 155411-25-9 (S)-[(C₁₀H₆(P(C₆H₅)2)C₉H₆N)Rh(cyclooctadiene)]CF₃SO₃ 

Relevant academic research and scientific papers

Asymmetric synthesis of QUINAP via dynamic kinetic resolution

A palladium-catalyzed, atroposelective C-P coupling process has been developed for the asymmetric synthesis of QUINAP and its derivatives in high enantiomeric excess. Bromide, triflate (OTf) and 4- methanesulfonylbenzenesulfonate (OSs) precursors were stu

Cu(II)-Catalyzed Construction of Heterobiaryls using 1-Diazonaphthoquinones: A General Strategy for the Synthesis of QUINOX and Related P,N Ligands

An efficient and straightforward method was developed for the synthesis of heterobiaryls using easily available N-oxides and diazonaphthoquinones under cheap Cu(II) catalysis. The developed method offered QUINOX and related congeners in a simple manner. A wide scope of important heterobiaryls was achieved with high site selectivity. The synthesized naphthols were transformed into the privileged related P,N ligands. Suitable resolution methods can directly afford the corresponding axially chiral heterobiaryls.

1-aryl isoquinoline compound and synthetic method thereof

The invention belongs to the field of organic synthesis, and discloses a 1-aryl isoquinoline compound, which has a structure shown as a general formula I. In the formula I, R1 and R2 are independentlyselected from hydrogen, alkyl, alkoxy, phenyl, halogen,

Synthesis of IAN-type N,N-Ligands via Dynamic Kinetic Asymmetric Buchwald-Hartwig Amination

The Pd0-catalyzed coupling of racemic heterobiaryl bromides, triflates, or nonaflates with aryl/alkyl primary amines using QUINAP as the ligand provides the corresponding axially chiral heterobiaryl amines with excellent yields and enantioselectivities. Reactivity and structural studies of neutral and cationic oxidative addition intermediates support a dynamic kinetic asymmetric amination mechanism based on the labilization of the stereogenic axis in the latter and suggest that coordination of the amine to the Pd center is the stereodetermining step.

Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4- naphthoquinones via one-pot aryne acyl-alkylation/condensation

A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from β-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the β-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP. The Royal Society of Chemistry 2009.

Practical preparation and resolution of 1-(2′-diphenylphosphino-1′-naphthyl)isoquinoline: A useful ligand for catalytic asymmetric synthesis

A practical synthesis of the atropisomerically chiral ligand QUINAP is described, followed by its efficient resolution into enantiomers by employing a deficiency of the chloropalladium complex derived from 1′-(R)-1′-(dimethylamino)-1-ethylnaphthalene. The X-ray structure of the ligand, which crystallises as a conglomerate, is reported.

Chelating retardation effect in nickel assisted phosphinatioa: Syntheses of atropisomeric P,N ligands

Ni(PPh3)2Cl2 was found to be an effective reagent in nickel assisted phosphination of biaryl O,N triflates with chlorodiphenylphosphine to yield atropisomeric P,N ligands. The chelating effect of the substrates in the reaction played an important role. Only the monodentate PPh3 rather than bidentate dppe (1,2-bis(diphenylphosphino)ethane) nickel complex was found to be an effective reagent. (C) 2000 Elsevier Science Ltd.

Synthesis and Resolution of 1-(2-Diphenylphosphino-1-naphthyl)isoquinoline; a P-N Chelating Ligand for Asymmetric Catalysis

A multistep synthesis resulting in a good yield of the title compound has been developed based on the Pd-catalysed coupling of 1-chloroisoquinoline and 2-methoxy-1-naphthylboronic acid (5).The product is converted into the corresponding trifluoromethanesu