Bis(dibenzylideneacetone)palladium

Bezeichnung:Bis(dibenzylideneacetone)palladium

CAS-Nr32005-36-0

Englisch Name:Bis(dibenzylideneacetone)palladium

CBNumberCB5132456

SummenformelC34H20O2Pd

Molgewicht566.95

MOL-Datei32005-36-0.mol

Bis(dibenzylideneacetone)palladium physikalisch-chemischer Eigenschaften

Schmelzpunkt	150°C
storage temp.	under inert gas (nitrogen or Argon) at 2–8 °C
Löslichkeit	Chloroform (Slightly)
Aggregatzustand	Fine Powder
Farbe	Red-brown to black
Wasserlöslichkeit	insoluble
Sensitive	Air & Moisture Sensitive
Stabilität	Hygroscopic
InChI	InChI=1S/2C17H10O.Pd/c218-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;/h21-10H;
InChIKey	WTAPZWXVSZMMDG-JZOPPWQGSA-N
SMILES	O=C1C2=C(C3C=CC=CC=3)[Pd]34562(C(C2C=CC=CC=2)=C3C(=O)C4=C5C2C=CC=CC=2)C(C2C=CC=CC=2)=C16
CAS Datenbank	32005-36-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/38
S-Sätze:	22-24/25-37/39-26
WGK Germany	3
TSCA	No
HS Code	28439000

Gefahreninformationscode (GHS)

Bis(dibenzylideneacetone)palladium Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/38:Reizt die Augen und die Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
purple brown
Verwenden
Hydrogenation, isomerization, carbonylation, oxidation, C-C bond formation.Bis(dibenzylideneacetone)palladium(0) is used as a reagent for the preparation of allylic substituted cyclopentadienes. It acts as a homogeneous catalyst as well as in the alkylation of allyl acetates by various nucleophiles. Further, it is used in Suzuki reaction.
Verwenden
Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Application
Bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) was employed as catalyst in the following studies:
Synthesis of isomeric 2-aryl-2,5-dihydrofurans, via Heck coupling of aryl bromides with alkenes using neopentyl phosphine ligands.
Heck reaction of benzyl trifluoroacetate and 2,3-dihydrofuran phosphoramidite ligand.
Allylation of stabilized anions.Cross coupling of allyl, alkenyl and aryl halides with organostannanes.
Cross coupling of vinyl halides with alkenyl zinc species.Carbonylation of alkenyl and aryl halides.
Employed with cyclic thiourea ligands in an efficient aerobic oxidation of alcohols to aldehydes and ketones.
Allgemeine Beschreibung
Bis(dibenzylideneacetone)palladium(0) (Pd(dba)₂) is an air stable Pd⁰ complex. It is a reagent for the synthesis of allylic substituted cyclopentadienes. It is a homogeneous catalyst. It catalyzes the alkylation of allyl acetates by various nucleophiles under mild conditions.
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
Synthese
Bis(dibenzylideneacetone)palladium(0) was prepared by reduction of PdCl2 with methanol in the presence of sodium acetate and dibenzylideneacetone, as dark-violet pre-cipitate with mp 152°C (150°C ).

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