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684821

Sigma-Aldrich

1,2-Bis(phenylsulfinyl)ethane palladium(II) acetate

greener alternative
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Synonym(s):
White catalyst
Empirical Formula (Hill Notation):
C18H20O6PdS2
CAS Number:
858971-43-4
Molecular Weight:
502.90
MDL number:
MFCD09842752
UNSPSC Code:
12161600
PubChem Substance ID:
329760926
NACRES:
NA.22

form

powder

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
reaction type: C-H Activation

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

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Greener Alternative Product

greener alternative category

Aligned,

storage temp.

−20°C

SMILES string

CC(=O)O[Pd]OC(C)=O.O=S(CCS(=O)c1ccccc1)c2ccccc2

InChI

1S/C14H14O2S2.2C2H4O2.Pd/c15-17(13-7-3-1-4-8-13)11-12-18(16)14-9-5-2-6-10-14;2*1-2(3)4;/h1-10H,11-12H2;2*1H3,(H,3,4);/q;;;+2/p-2

InChI key

SNNYSJNYZJXIFE-UHFFFAOYSA-L

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.

Application

White Catalyst: A Catalyst for Allylic C–H Oxidation and Amination
Macrolactonization via Hydrocarbon Oxidation
Catalyst for allylic C-H oxidation, useful for preparation of branched allylic esters, macrocycles, and amino alcohol derivatives.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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syn-1,2-Amino alcohols via diastereoselective allylic C-H amination.
Kenneth J Fraunhoffer et al.
Journal of the American Chemical Society, 129(23), 7274-7276 (2007-05-23)
Kenneth J Fraunhoffer et al.
Journal of the American Chemical Society, 128(28), 9032-9033 (2006-07-13)
A novel Pd/sulfoxide-catalyzed macrolactonization reaction of linear omega-alkenoic acids is reported that proceeds via serial ligand-catalyzed allylic C-H oxidation. The scope of this macrolactonization appears to be very broad. Aryl, alkyl, and (Z)-alpha,beta-unsaturated acids are all competent nucleophiles for this

Articles

White Catalyst

The "White catalyst" by Professor M. Christina White enables allylic carbon functionalization, demonstrating exceptional catalytic activity.

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