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768146

Sigma-Aldrich

Dichloro[9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene]palladium(II)

95%

Synonym(s):

(SP-4-2)-Dichloro[1,1′-(9,9-dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine-κP]]-palladium

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About This Item

Empirical Formula (Hill Notation):
C39H32Cl2OP2Pd
CAS Number:
205319-10-4
Molecular Weight:
755.94
MDL number:
MFCD14155707
UNSPSC Code:
12161600
PubChem Substance ID:
329767359
NACRES:
NA.22

Assay

95%

form

solid

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

280-287 °C (decomposition)

SMILES string

Cl[Pd]Cl.CC1(C)c2cccc(P(c3ccccc3)c4ccccc4)c2Oc5c(cccc15)P(c6ccccc6)c7ccccc7

InChI

1S/C39H32OP2.2ClH.Pd/c1-39(2)33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)40-38-34(39)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32;;;/h3-28H,1-2H3;2*1H;/q;;;+2/p-2

InChI key

HEYONDYPXIUDCK-UHFFFAOYSA-L

Application

Effective catalyst for carbonylation of aryl halides

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Tetsuaki Fujihara et al.
Chemical communications (Cambridge, England), 48(64), 8012-8014 (2012-07-10)
Aryl formates are efficient carbon monoxide sources in palladium-catalyzed esterification of aryl halides. The carbonylation readily proceeds at ambient pressure without the use of external carbon monoxide to afford the corresponding esters in high yields.
Jennifer Albaneze-Walker et al.
Organic letters, 6(13), 2097-2100 (2004-06-18)
[reaction: see text] Optimized conditions are described that effect the carbonylation of diverse heterocyclic chlorides to yield the desired alkyl esters. In addition, bromoanilines and bromoanisoles, which normally are poor substrates under standard carbonylation protocols, were efficiently converted to the
Pan Xie et al.
Journal of the American Chemical Society, 134(24), 9902-9905 (2012-06-06)
A new strategy for generating benzylpalladium reactive species from toluenes via nondirected C(sp(3))-H activation has been developed. This led to construction of an efficient Pd-catalyzed reaction protocol for the oxidative carboxylation of benzylic C-H bonds to form substituted 2-phenylacetic acid

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