127593-28-6

Basic information

• Product Name: [(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II) CHLORIDE
• Synonyms: [(S)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II)CHLORIDE;2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYLPALLADIUM(II) CHLORIDE;PALLADIUM, [(1S)-[1,1''-BINAPHTHALENE]-2,2''-DIYLBIS[DIPHENYLPHOSPHINE-.KAPPA.P]]DICHLORO-, (SP-4-2)-;REF DUPL: [(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]palladium (II) chloride;Dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II), min. 98%;Dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladiuM(II),Min.98%;Dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladiuM(II),98% (S-BINAP)PdCl2;[(S)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II)
• CAS NO: 127593-28-6
• Molecular Formula: C₄₄H₃₂Cl₂P₂Pd
• Molecular Weight: 800
• EINECS: 1312995-182-4
• Product Categories: Pd
• Mol File: 127593-28-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: >300°C
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: [(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II) CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: [(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II) CHLORIDE(127593-28-6)
• EPA Substance Registry System: [(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II) CHLORIDE(127593-28-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 127593-28-6(Hazardous Substances Data)

Usage

Reaction

Catalyst precursor, with AgBF4 , for the enantioselective addition of silyl ethers, to imines to produce β-amino ketones, and to aldehydes to produce 3-hydroxy-1-propanone aldol addition products. Catalyst precursor, with AgSbF6, for the asymmetric carbonyl-ene reaction. Catalyst precursor for hetero Diels-Alder reaction of simple dienes with aldehydes and aryl glyoxals.

Upstream product

• 12107-56-1 dichloro(1,5-cyclooctadiene)palladium(II) 
• 21264-30-2 dichloro bis(acetonitrile) palladium(II) 
• 76189-55-4 (R)-(+)-2,2’-bis(diphenylphosphino)-1,1’-binaphthalene 
• 76144-87-1 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 
• 14592-56-4 bis(acetonitrile)palladium(II) chloride 
• 76144-87-1 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 
• 76144-87-1 (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) 

Downstream Products

• 320635-27-6 Pd(C₆H₅)2PC₂₀H₁₂P(C₆H₅)2(SO₃CF₃)⁽¹⁺⁾*CF₃SO₃^(1-)=Pd((C₆H₅)2PC₂₀H₁₂P(C₆H₅)2)(SO₃CF₃)2 
• 207230-28-2 ((C₆H₅)2PC₁₀H₆)2Pd(ClO₄)2 
• 171415-13-7 [Pd((R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)(H₂O)(triflate)](triflate) 
• 171415-13-7 (C₁₀H₆)2(P(C₆H₅)2)2Pd(OSO₂CF₃)2*H₂O 
• 314294-00-3 H₂N[2,6-(2,4,6-(i-Pr)₃C₆H₂)₂(C₆H₃)] 

Relevant articles and documents

Visible-Light-Induced Palladium-Catalyzed Dehydrogenative Carbonylation of Amines to Oxalamides

The palladium-catalyzed oxidative carbonylation of amines toward the synthesis of oxalamides has been established around 30 years ago and it usually needs the presence of (over)stoichiometric amounts of oxidant. In this work, the first transformation of this type in which the oxidant was replaced by visible light is described. The new approach uses a simple robust Pd complex, which can even be partially recycled. A mechanistic reason is provided and supported by control experiments and EPR studies, showing that PdI was formed and Pd0 was the active species. Both nitrogen- and the intermediate acyl radical can be detected. Moreover, the formation of hydrogen was confirmed by gas GC.

Conformational flexibility of palladium BINAP complexes explored by X-ray analyses and DFT studies

Several crystal structures and a theoretical DFT structure of the important catalyst (BINAP)PdCl2 (BINAP: 2,2′-bis(diphenylphosphino)-1, 1′-binaphthyl) have been determined. The conformational flexibilities of the BINAP backbone and of the phenyl rings do not seem to be coupled. Two novel parameter have been introduced that define the Π-Π stacking between the phenyl and biaryl rings in systems similar to the BINAP ligand, as well as the delta angle that is sensitive to the important interaction of the exchangeable ligands of the palladium with the equatorial phenyl rings of the BINAP. Furthermore, the calculated bite angle is 3° larger than the experimentally determined bite angles.

Electronic behavior of calcined material obtained from 2,2-diphenylphosphino-1,1-binaphthyldichloro palladium

The calcinations of 2,2-diphenylphosphino-1,1-binaphthyldichloro palladium under an argon atmosphere gave nano-sized Pd5P2/carbon cluster composite material. The ESR spectral examination of the material, and the reaction of either methylene blue or 2,3,5-trimethylhydroquinone in the presence of the material revealed that the calcined material has a visible light-responsive oxidation-reduction function through an electron transfer from the carbon clusters to the Pd5P2 particles.