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756482

Sigma-Aldrich

P(t-Bu)3 Pd G2

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C24H37ClNPPd
CAS Number:
1375325-71-5
Molecular Weight:
512.40
MDL number:
MFCD21608496
UNSPSC Code:
12161600
PubChem Substance ID:
329766544
NACRES:
NA.22

form

solid

Quality Level

100

feature

generation 2

reaction suitability

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)

functional group

phosphine

SMILES string

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

InChI key

ZVSLIOFJVMRWHJ-UHFFFAOYSA-M

General description

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).

Application

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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

Articles

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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