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412740

Sigma-Aldrich

Bis(triphenylphosphine)palladium(II) dichloride

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:
13965-03-2
Molecular Weight:
701.90
Beilstein/REAXYS Number:
4935975
EC Number:
237-744-2
MDL number:
MFCD00009593
UNSPSC Code:
12161600
PubChem Substance ID:
24865821
NACRES:
NA.22

form

solid

Quality Level

200

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

SMILES string

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

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

InChI key

YNHIGQDRGKUECZ-UHFFFAOYSA-L

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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

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
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
GHS07

signalword

Warning

hcodes

H317,H413

Hazard Classifications

Aquatic Chronic 4 - Skin Sens. 1A

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN5864
MKCM1875
MKCH9617
MKCJ2054
MKCJ3390

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Saa, J. M.; Martorell, G.; Garcia-Raso, A.
The Journal of Organic Chemistry, 57, 678-678 (1992)
Catalysis Today, 66, 53-61 (2001)
T Djekić et al.
Journal of chromatography. A, 1142(1), 32-38 (2006-10-20)
The goal of this paper is the evaluation of functionalized silica's for the recovery of homogeneous catalysts by adsorption via its metal centre. As model catalysts, we selected bis(triphenylphosphine)cobalt(II)dichloride (CoCl(2)(PPh(3))(2)), bis(triphenylphosphine)palladium(II)dichloride (PdCl(2)(PPh(3))(2)) and tris(triphenylphosphine)rhodium(I)dichloride (RhCl(PPh(3))(3)). Twelve functionalized groups selected from
Negishi, E.; Ay, M.; et al
Tetrahedron Letters, 34, 1437-1437 (1993)
Tetrahedron, 62, 9548-9548 (2006)
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Articles

Transition-Metal Catalysts

A variety of transition-metal catalysts for the Suzuki coupling reaction are now available in our catalog. The majority of these catalysts are palladium- and nickelbased, typically utilizing phosphine-derived ligands.

Heck Reaction Applications & Products

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.

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