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366315

Sigma-Aldrich

Tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct

Synonym(s):

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

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250 MG
$50.60
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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

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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

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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.[1]

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.[2]
  • As palladium source in the asymmetric transformations of 3,4-epoxy-1-butene.[3]
  • As catalyst for the Heck cross-coupling reaction of iodobenzene with styrene.[1]
  • As cyclization catalyst.[4][5]
  • As catalyst for [2+2+2] cycloaddtion of didehydrotriphenylenes to the corresponding extended triphenylenes.[6]
  • As catalyst for the carbonylation of b,b-imidoyl iodides to the corresponding imidate esters used, in turn, to prepare cyclic, quaternary amino acids.[7]

pictograms

Health hazardExclamation mark
GHS08,GHS07

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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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Certificates of Analysis (COA)

Lot/Batch Number
MKCW4365
MKCV6487
MKCS9844
MKCQ1439
MKCV1848

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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)
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
Chemistry (Weinheim An Der Bergstrasse, Germany), 12, 5657-5657 (2006)
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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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