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655414

Sigma-Aldrich

2-(2′-Di-tert-butylphosphine)biphenylpalladium(II) acetate

97%

Synonym(s):

Palladium, (acetato-ΚO) [2′-[bis (1,1 dimethylethyl) phosphino-ΚP] [1,1′-biphenyl]-2-yl ΚC]

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About This Item

Empirical Formula (Hill Notation):
C22H29O2PPd
CAS Number:
577971-19-8
Molecular Weight:
462.86
MDL number:
MFCD04117716
UNSPSC Code:
12352300
PubChem Substance ID:
24884102
NACRES:
NA.22

Assay

97%

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

130-140 °C (dec.) (lit.)

SMILES string

CC(=O)[Pd]1c2ccccc2-c3ccccc3[PH]1(C(C)(C)C)C(C)(C)C

InChI

1S/C20H26P.C2H4O2.Pd/c1-19(2,3)21(20(4,5)6)18-15-11-10-14-17(18)16-12-8-7-9-13-16;1-2(3)4;/h7-12,14-15H,1-6H3;1H3,(H,3,4);/q;;+1/p-1

InChI key

IEYDYAASBZOBOC-UHFFFAOYSA-M

General description

2-(2′-Di-tert-butylphosphine)biphenylpalladium(II) acetate is a novel, air- and moisture-and thermally stable catalyst.

Application

It can be used as a pre-catalyst for the amination of aryl chlorides. It can also be used to prepare N-methyl-6-heterocyclic-1-oxoisoindoline derivatives via Buchwald-Hartwig amination reaction of N-methyl-6- bromoisoindoline-1-one with different amines under microwave condition.
Precatalyst for Buchwald-Hartwig amination reaction.

Storage Class Code

13 - Non 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

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Certificates of Analysis (COA)

Lot/Batch Number
22296BPV
22296BP
01496MK
19796EK
51397KJ

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Synthesis of N-Methyl-6-heterocyclic-1-oxoisoindoline Derivatives by Microwave Assisted Buchwald-Hartwig Amination.
Kumar CK, et al.
The Journal of Organic Chemistry, 8(3), 1108-1113 (2011)
An air and thermally stable one-component catalyst for the amination of aryl chlorides.
Zim D and Buchwald SL.
Organic Letters, 5(14), 2413-2415 (2003)

Articles

Palladacycle Coupling Catalysts

Palladacyclic catalysts by Bedford's group facilitate coupling reactions with low catalyst loadings and challenging aryl chlorides.

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