Allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II) - ≥99.95% metals basis , CAS No.478980-03-9

CAS: 478980-03-9 Cat. No.: A284055 Molecular Weight: 571.53 EC Number: 625-870-4 PubChem CID: 254777602

GRADE & PURITY ≥99.95% metals basis

Synonyms

Umicore CX21 | (NHC)Pd(allyl)Cl | Allylchloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]palladium(II)

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Overview

Allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II) is an air-stable, well-defined palladium N-heterocyclic carbene complex, which can efficiently catalyze α-arylation of ketones.
Catalyst for the arylation of ketones, Suzuki coupling reaction, Buchwald-Hartwig amination reaction, dehalogenation of aryl chlorides, and oxidation of secondary alcohols.

Product class
M-P, Homogeneous Catalysts, N-Heterocyclic Carbene Ligands, M-C, Allyl Ligands, IPr, Bidentate Ligands

Reaction type
Cross Coupling Reactions with Arenes, Amination, Buchwald-Hartwig Aminaton, Alpha Arylation, Dehalogenation, Kumada Coupling Reaction, Mizoroki Heck Coupling Reaction, Oxidation, Suzuki-Miyaura Coupling Reaction, Dehalogenation, Oxidation, Telomerization

Chemical properties

Chemical formula

C30H41N2ClPd

Empirical formula

[(IPr)Pd(allyl)CI]

Molecular weight

571.54

Metal

Pd

Theoretical metal content

19

Physical state

crystalline

Metal purity

99.95

Applications & references

Palladium catalyzed anaerobic oxidation of secondary alcohols under mild reaction conditions.

Reference: J. Org. Chem. 2011, 76, 1390. (DOI: 10.1021/jo102385u)

One-pot oxidation / α-ketone arylation of secondary alcohols.

Reference: J. Org. Chem. 2011, 76, 1390. (DOI: 10.1021/jo102385u)

Palladium catalyzed Buchwald-Hartwig-Reaction at room temperature.

Reference: J. Am. Chem. Soc. 2006, 128, 4101. (DOI: 10.10217ja057704z)

α-Arylation of propiophenone.

Reference: Org. Lett. 2002, 4, 4053 (DOI: 10.1021/ol026745m)

Intramolecular arylamination step in the total synthesis of cryptocarya alkaloids.

Reference: Synlett 2003, 12, 1871 (DOI: 10.1055/s-2003-41468)

Dehalogenation reaction.

Reference: J. Org. Chem. 2004, 69, 3173 (DOI: 10.1021/jo035834p)

Suzuki-Miyaura coupling reaction.

Reference: J. Am. Chem. Soc. 2006, 128, 4101. (DOI: 10.10217ja057704z)

Specifications

Synonyms

Umicore CX21 | (NHC)Pd(allyl)Cl | Allylchloro[1, 3-bis(2, 6-diisopropylphenyl)imidazol-2-ylidene]palladium(II)

Specifications & Purity

≥99.95% metals basis

Storage

Store at 2-8°C, Protected from light, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99.95% metals basis

Names and Identifiers

• Canonical Smiles: [CH2][CH][CH2].CC(C)c1cccc(C(C)C)c1N2C=CN(C2[Pd]Cl)c3c(cccc3C(C)C)C(C)C
• InChIKey: YVIDBHQABBIAAW-UHFFFAOYSA-M
• INCHI: 1S/C27H37N2.C3H5.ClH.Pd/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;1-3-2;;/h9-21H,1-8H3;3H,1-2H2;1H;/q;;;+1/p-1
• WGK Germany: 3
• PubChem CID: 254777602
• Molecular Weight: 571.53

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Melt Point(°C): >300°C