CAS 12131-44-1 Palladium(II)(π-cinnamyl) Chloride Dimer

Synonyms

12131-44-1;Palladium(|Eth-cinnamyl) chloride dimer;AK136149;PALLADIUM(PI-CINNAMYL) CHLORIDE DIMER;Di- -chlorobis[(1,2,3- )-1-phenyl-2-propen-1-yl]dipalladium;Di-|I-chlorobis[(1,2,3-|C)-1-phenyl-2-propen-1-yl]dipalladium;Di-|I-chlorobis[(1,2,3-|C)-1-phenyl-2-propenyl]dipalladium(II);Di-mu-chlorobis[(1,2,3-eta)-1-phenyl-2-propen-1-yl]dipalladium;

IUPAC Name

palladium(2+);prop-2-enylbenzene;dichloride;

Molecular Weight

518.082g/mol

Molecular Formula

C18H18Cl2Pd2;

Canonical SMILES

C=C[CH-]C1=CC=CC=C1.C=C[CH-]C1=CC=CC=C1.[Cl-].[Cl-].[Pd+2].[Pd+2];

InChI

InChI=1S/2C9H9.2ClH.2Pd/c2*1-2-6-9-7-4-3-5-8-9;;;;/h2*2-8H,1H2;2*1H;;/q2*-1;;;2*+2/p-2;

InChI Key

PHDNDSSMEIRHSI-UHFFFAOYSA-L;

Complexity

Covalently-Bonded Unit Count

Exact Mass

517.886g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

515.886g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

Palladium(II)(π-cinnamyl) Chloride Dimer serves as a versatile palladium precursor in a wide range of organic synthesis applications. This compound is pivotal in facilitating ammonia cross-coupling reactions for the synthesis of arylamines and enabling the conversion of aryl triflates to fluorides. It acts as a source of palladium for the asymmetric α-arylation of amides and is instrumental in preparing palladium catalysts for the carbonylative arylation of ketones, yielding vinylbenzoate compounds. Additionally, it is a precursor for catalysts used in the Buchwald-Hartwig amination of (hetero)aryl chlorides and in the arylative dearomatization of phenols. This compound also supports the cross-coupling of aryl chlorides and amines and the α-arylation of aldehydes, showcasing its importance in transition-metal-mediated organic syntheses.

January 30, 2025

Reliable Catalyst for Advanced Synthesis

The Palladium(II)(π-cinnamyl) Chloride Dimer from Alfa Chemistry substantially improved our ammonia cross-coupling reactions in synthesizing arylamines. It's a robust, versatile catalyst essential for efficient research workflows. Highly recommend for industrial applications.