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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:
Molecular Weight:
462.86
MDL number:
UNSPSC Code:
12352300
PubChem Substance ID:
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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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

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

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

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

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

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