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756482

Sigma-Aldrich

P(t-Bu)3 Pd G2

Sinónimos:

Chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)] palladium(II)

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About This Item

Fórmula empírica (notación de Hill):
C24H37ClNPPd
Número de CAS:
1375325-71-5
Peso molecular:
512.40
Número MDL:
MFCD21608496
Código UNSPSC:
12161600
ID de la sustancia en PubChem:
329766544
NACRES:
NA.22

formulario

solid

Nivel de calidad

100

Características

generation 2

idoneidad de la reacción

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
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
reaction type: Cross Couplings

mp

167-170 °C (decomposition)

grupo funcional

phosphine

cadena SMILES

NC1=C(C2=CC=CC=C2[Pd]Cl)C=CC=C1.CC(C)(C)P(C(C)(C)C)C(C)(C)C

InChI

1S/C12H10N.C12H27P.ClH.Pd/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-10(2,3)13(11(4,5)6)12(7,8)9;;/h1-6,8-9H,13H2;1-9H3;1H;/q;;;+1/p-1

Clave InChI

ZVSLIOFJVMRWHJ-UHFFFAOYSA-M

Descripción general

P(t-Bu)3 Pd G2 (Chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)] palladium(II)) is a second generation (G2) precatalyst containing a biphenyl-based ligand. Product participates in various palladium catalyzed cross-coupling reactions, C-C, C-N and C-O bond formation reactions, and Suzuki-Miyaura coupling reactions. It generates active Pd catalyst at room temperature in the presence of weak phosphate or carbonate bases. It has been proposed as an active catalyst for use in Stille reactions of aryl halides (bromides and chlorides).

Aplicación

P(t-Bu)3 Pd G2 (Chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)] palladium(II), Pd/P(t-Bu)3) may be used as catalyst in the following studies:
  • Synthesis of sterically hindered biaryls (tetra-ortho-substituted), via cross-coupling reactions of aryl chlorides.
  • Stille cross-couplings reactions of aryl chloride.
  • Synthesis of chloropeptin I, via Stille cross-coupling reaction.
  • Heck reaction.
  • Negishi cross-coupling reactions.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
SHBM5348
SHBL4565
SHBL0980
SHBK3497
SHBJ1716

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Adam F Littke et al.
Journal of the American Chemical Society, 124(22), 6343-6348 (2002-05-30)
Pd/P(t-Bu)(3) serves as an unusually reactive catalyst for Stille reactions of aryl chlorides and bromides, providing solutions to a number of long-standing challenges. An unprecedented array of aryl chlorides can be cross-coupled with a range of organotin reagents, including SnBu(4).
Gregory C Fu
Accounts of chemical research, 41(11), 1555-1564 (2008-10-25)
Metal-catalyzed coupling reactions of aryl electrophiles with organometallics and with olefins serve as unusually effective tools for forming new carbon-carbon bonds. By 1998, researchers had developed catalysts that achieved reactions of aryl iodides, bromides, and triflates. Nevertheless, many noteworthy challenges

Artículos

Scale-Up Guide: Buchwald-Hartwig Amination Reaction

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form. Once activated by base under the reaction conditions they become sensitive to air. To best enable scale-up success, the use of standard Schlenk technique is recommended.

Scale-Up Guide: Buchwald-Hartwig Amination Reaction

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form. Once activated by base under the reaction conditions they become sensitive to air. To best enable scale-up success, the use of standard Schlenk technique is recommended.

KitAlysis™ C-N (Buchwald-Hartwig) High-Throughput Screening Kit

All contents in the foil bag are weighed, plated, packed, and sealed in a glove box under nitrogen.

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