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676578

Sigma-Aldrich

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

greener alternative

Synonym(s):

Pd(t-Bu3P)2

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About This Item

Empirical Formula (Hill Notation):
C24H54P2Pd
CAS Number:
53199-31-8
Molecular Weight:
511.05
MDL number:
MFCD03094580
UNSPSC Code:
12161600
PubChem Substance ID:
24884857
NACRES:
NA.22

form

solid

Quality Level

100

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

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

258-272 °C

greener alternative category

, Aligned

storage temp.

−20°C

SMILES string

[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;

InChI key

MXQOYLRVSVOCQT-UHFFFAOYSA-N

General description

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.

Application

  • 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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP7205
MKCQ4556
MKCP6840
MKCN4061
MKCM0503

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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
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.
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)
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Articles

Procedures for Transition-Metal-Catalyzed Cross-Coupling Reactions in Water at Room Temperature using TPGS-750-M

TPGS-750-M, a second generation surfactant, is useful for room temperature, palladium and ruthenium-catalyzed reactions in water. Reactions include the Heck reaction, Suzuki-Miyaura reaction, Sonogashira reaction, Buchwald-Hartwig amination reaction, Negishi reaction, and olefin metathesis.

Protocols

Transition-Metal-Catalyzed Cross-Coupling Reactions in Water at Room Temperature using TPGS-750-M

TPGS-750-M, a second generation surfactant, may be used in water at room temperature for Buchwald-Hartwig Amination, Suzuki-Miyaura reactions, Heck reactions, Sonogashira reactions, Negishi reactions, and olefin metathesis.

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