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671916

Sigma-Aldrich

trans-Bis(acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II)

98%

Synonym(s):

trans-Di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II), trans-Di-μ-acetatobis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium, Herrmann′s catalyst, Herrmann′s palladacycle, Herrmann-Beller catalyst, Herrmann-Beller palladacycle, cataCXium® C

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About This Item

Empirical Formula (Hill Notation):
C46H46O4P2Pd2
CAS Number:
172418-32-5
Molecular Weight:
937.64
MDL number:
MFCD01075746
UNSPSC Code:
12161600
PubChem Substance ID:
329760447
NACRES:
NA.22

Assay

98%

reaction suitability

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
core: palladium
reagent type: ligand
reaction type: Asymmetric synthesis

functional group

phosphine

SMILES string

CC(=O)O[Pd]Cc1ccccc1P(c2ccccc2C)c3ccccc3C.CC(=O)O[Pd]Cc4ccccc4P(c5ccccc5C)c6ccccc6C

InChI

1S/2C21H20P.2C2H4O2.2Pd/c2*1-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3;2*1-2(3)4;;/h2*4-15H,1H2,2-3H3;2*1H3,(H,3,4);;/q;;;;2*+1/p-2

InChI key

YRGPDGDJUOTURS-UHFFFAOYSA-L

General description

trans-Bis(acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) is a useful catalyst for Heck reaction.
sold in collaboration with Solvias AG

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
trans-Bis(acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) is a useful catalyst for C-C and C-N cross coupling reaction.

Legal Information

US5831107
cataCXium is a registered trademark of Umicore AG & Co. KG

Storage Class Code

11 - Combustible Solids

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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Louie, J.; Hartwig, J. F.
Angewandte Chemie (International Edition in English), 35, 2359-2359 (1996)
Brody, M. S.; Finn, M. G.
Tetrahedron Letters, 40, 415-415 (1999)
trans-Di (?-acetato)-bis [o-(di-o-tolylphosphino) benzyl] dipalladium (II).
Speicher A, et al.
J. Prakt. Chem., 341(6), 605-608 (1999)
Herrmann, W. A.; Brossmer, C.
Angewandte Chemie (International Edition in English), 34, 1844-1844 (1995)
Alphonse Tenaglia et al.
Organic letters, 8(19), 4315-4318 (2006-09-08)
Herrmann-Beller (H-B) phosphapalladacycle selectively catalyzed the addition of terminal alkynes across one double bond of norbornadiene to afford exo-5-alkynyl-bicyclo[2.2.1]hept-2-enes. The reaction shows general applicability to various functionalized alkynes and bicyclo[2.2.1]hepta-2,5-dienes. Insights into the mechanism of this reaction are discussed.
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Articles

cataCXium®

cataCXium® - Ligands and Complexes for Efficient Cross-Coupling Reactions. Cross-coupling reactions are an important class of catalytic transformations with applications in polymer science as well as in the fine chemicals and pharmaceutical industries.

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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