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671916

Sigma-Aldrich

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

98%

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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
Empirical Formula (Hill Notation):
C46H46O4P2Pd2
CAS Number:
172418-32-5
Molecular Weight:
937.64
MDL number:
MFCD01075746
UNSPSC Code:
12352300
PubChem Substance ID:
329760447
NACRES:
NA.22

Quality Level

100

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

Related Categories

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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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.
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.
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