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676578

Sigma-Aldrich

Bis(tri-tert-butylphosphine)palladium(0)

greener alternative

Sinonimo/i:

Pd(t-Bu3P)2

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About This Item

Formula empirica (notazione di Hill):
C24H54P2Pd
Numero CAS:
53199-31-8
Peso molecolare:
511.05
Numero MDL:
MFCD03094580
Codice UNSPSC:
12161600
ID PubChem:
24884857
NACRES:
NA.22

Forma fisica

solid

Impiego in reazioni chimiche

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

Caratteristiche più verdi

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

Punto di fusione

258-272 °C

Categoria alternativa più verde

, Aligned

Temperatura di conservazione

−20°C

Stringa SMILE

[Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C

InChI

1S/2C12H27P.Pd/c2*1-10(2,3)13(11(4,5)6)12(7,8)9;/h2*1-9H3;
MXQOYLRVSVOCQT-UHFFFAOYSA-N

Categorie correlate

Descrizione generale

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.

Applicazioni

  • Catalyst for Suzuki coupling on a multisubstituted sp3-carbon (eq. 1)
  • Catalyst for Stille coupling reaction of aryl chlorides (eq. 2)
  • Catalyst for Negishi coupling reaction (eq. 3)
  • Catalyst for Heck coupling to form tetrasubstituted olefins (eq. 4)
  • Catalyst for Buchwald-Hartwig amination of aryl halide (eq. 5)
  • Catalyst for carbonylation of aryl halides with carbamoylsilanes (eq. 6)
Catalyst for greener Heck reaction in TPGS-750-M.

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

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Kenichiro Itami et al.
Journal of the American Chemical Society, 126(38), 11778-11779 (2004-09-24)
We have developed a programmable and diversity-oriented synthetic scheme for tetrasubstituted olefins through a site-selective and sequential assembly of pi-components onto a C=C core of vinyl 2-pyrimidyl sulfide. Noteworthy features are that (i) all components assembled stem from readily available
Ryoichi Kuwano et al.
The Journal of organic chemistry, 67(18), 6479-6486 (2002-08-31)
The amination of aryl halides in the presence of inexpensive and air-stable alkali metal hydroxide bases and Pd[P(t-Bu)3]2 as catalyst gave arylamines in high yields. The reactions were conducted with a catalytic amount of cetyltrimethylammonium bromide as phase-transfer agent and
Robert F Cunico et al.
Organic letters, 5(26), 4947-4949 (2003-12-20)
Alkenyl chlorides and bromides are converted into tertiary enamides by treatment with a carbamoylsilane in toluene at 110 degrees C in the presence of phosphine-palladium(0) catalysts. [reaction: see text]
Negishi, E.-I.; Shi, J.-C.; Zeng, X.
Tetrahedron, 61, 9886-9886 (2005)
Kohei Endo et al.
Journal of the American Chemical Society, 132(32), 11033-11035 (2010-08-12)
The palladium-catalyzed Suzuki-Miyaura cross-coupling on a multisubstituted sp(3)-carbon in 1,1-diborylalkanes was achieved at room temperature. The generation of a monoborate intermediate by virtue of the adjacent B atom could result in the chemoselective coupling reaction under ambient conditions.
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Articoli

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

Protocolli

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

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