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Merck
CN

412740

Bis(triphenylphosphine)palladium(II) dichloride

solid

Synonym(s):

Dichlorobis(triphenylphosphine)palladium(II), Palladium(II)bis(triphenylphosphine) dichloride, PdCl2(PPh3)2

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About This Item

Linear Formula:
[(C6H5)3P]2PdCl2
CAS Number:
Molecular Weight:
701.90
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12161600
EC Number:
237-744-2
MDL number:
Beilstein/REAXYS Number:
4935975
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Product Name

Bis(triphenylphosphine)palladium(II) dichloride,

InChI key

YNHIGQDRGKUECZ-UHFFFAOYSA-L

InChI

1S/2C18H15P.2ClH.Pd/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;/h2*1-15H;2*1H;/q;;;;+2/p-2

SMILES string

Cl[Pd]Cl.c1(P(c2ccccc2)c3ccccc3)ccccc1.c4(P(c5ccccc5)c6ccccc6)ccccc4

form

solid

reaction suitability

core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst

Quality Level

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General description

Bis(triphenylphosphine)palladium(II) dichloride is an organometallic complex. It is an efficient cross-coupling catalyst for C-C coupling reaction, such as Negishi coupling, Suzuki coupling, Sonogashira coupling and Heck coupling reaction. Detection of bis(triphenylphosphine)palladium(II) dichloride by electrospray ionization quadrupole ion trap mass spectrometry using different imidazolium salts as the charge carrier has been reported. It is employed as catalyst for the Heck reaction medium.

Application

Bis(triphenylphosphine)palladium(II) dichloride was employed in the following studies:
  • As model catalyst for the evaluation of functionalized silica′s for the adsorptive recovery of homogeneous catalysts, via its interaction with metal centre.
  • As catalyst in the synthesis of diphenylacetylene.
  • One-pot synthesis of furoquinolines, via Pd-catalyzed Sonogashira coupling followed by Cu(I) catalyzed ring closure.
  • Catalyst for Sonogashira coupling of aryl alkynes to 2-bromothiazole and 2-bromothiophene.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Aquatic Chronic 4 - Skin Sens. 1A

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Negishi, E.; Coperet, C., et al.
Journal of the American Chemical Society, 118, 5904-5904 (1996)
A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines.
Sonogashira K, et al.
Tetrahedron Letters, 16(50), 4467-4470 (1975)
Tetrahedron, 62, 9548-9548 (2006)
Negishi, E.; Ay, M.; et al
Tetrahedron Letters, 34, 1437-1437 (1993)
Saa, J. M.; Martorell, G.; Garcia-Raso, A.
The Journal of Organic Chemistry, 57, 678-678 (1992)

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