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Sigma-Aldrich

Tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct

Synonym(s):

Dipalladium-tris(dibenzylideneacetone)chloroform complex, Pd2(dba)3 · CHCl3

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About This Item

Linear Formula:
(C6H5CH=CHCOCH=CHC6H5)3Pd2 · CHCl3
CAS Number:
52522-40-4
Molecular Weight:
1035.10
MDL number:
MFCD00075479
UNSPSC Code:
12161600
PubChem Substance ID:
24862642
NACRES:
NA.22

form

solid

Quality Level

100

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
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

mp

131-135 °C (lit.)

SMILES string

[Pd].[Pd].ClC(Cl)Cl.O=C(/C=C/c1ccccc1)\C=C\c2ccccc2.O=C(/C=C/c3ccccc3)\C=C\c4ccccc4.O=C(\C=C\c5ccccc5)/C=C/c6ccccc6

InChI

1S/3C17H14O.CHCl3.2Pd/c3*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;2-1(3)4;;/h3*1-14H;1H;;/b3*13-11+,14-12+;;;

InChI key

LNAMMBFJMYMQTO-FNEBRGMMSA-N

General description

Tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (Pd2dba3·CHCl3) is reported to serve as effective precatalysts, or precursors to the active Pd(0) catalyst.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (Pd2dba3·CHCl3) was used in the following studies:
  • To compose the catalytic system for the preparation of homoallylpalladium complexes.These complexes underwent in situ Stille type cross coupling with various vinyltin reagents to afford the cyclized products bearing allyl appendages.
  • As palladium source in the asymmetric transformations of 3,4-epoxy-1-butene.
  • As catalyst for the Heck cross-coupling reaction of iodobenzene with styrene.
  • As cyclization catalyst.
  • As catalyst for [2+2+2] cycloaddtion of didehydrotriphenylenes to the corresponding extended triphenylenes.
  • As catalyst for the carbonylation of b,b-imidoyl iodides to the corresponding imidate esters used, in turn, to prepare cyclic, quaternary amino acids.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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The Journal of Organic Chemistry, 55, 3388-3388 (1990)
Palladate salts from ionic liquids as catalysts in the Heck reaction.
Gayet M,et al.
ARKIVOC (Gainesville, FL, United States), 17, 61-76 (2008)
Tetrahedron Letters, 30, 651-651 (1989)
Palladium (II)-catalyzed tandem cyclic carbopalladation-vinylation of enyne compounds.
Yamada H, et al.
Tetrahedron Letters, 38(17), 3027-3030 (1997)
Santos Fustero et al.
Organic letters, 8(18), 4129-4132 (2006-08-25)
The synthesis of new beta,beta-difluorinated cyclic quaternary alpha-amino acid derivatives 1 in which a ring-closing metathesis reaction (RCM) constitutes the key step is described. The approach employs imidoyl chlorides 3 as fluorinated building blocks, and the overall process involves the
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