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761605

Sigma-Aldrich

BrettPhos Pd G3

98%

Synonyme(s) :

[(2-Di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′- triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′ -biphenyl)]palladium(II) methanesulfonate methanesulfonate

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About This Item

Formule empirique (notation de Hill):
C48H66NO5PPdS
Numéro CAS:
1470372-59-8
Poids moléculaire :
906.50
Numéro MDL:
MFCD22572666
Code UNSPSC :
12352300
ID de substance PubChem :
329766562
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

98%

Forme

solid

Caractéristiques

generation 3

Capacité de réaction

reaction type: Buchwald-Hartwig Cross Coupling Reaction

Pertinence de la réaction

reagent type: catalyst
core: palladium
reaction type: Cross Couplings

Pf

150-193 °C (decomposition)

Groupe fonctionnel

amine

Chaîne SMILES 

CS(=O)(O[Pd]c1c(c2c(N)cccc2)cccc1)=O.COc3c(P(C4CCCCC4)C5CCCCC5)c(c6c(C(C)C)cc(C(C)C)cc6C(C)C)c(OC)cc3

InChI

1S/C35H53O2P.C12H10N.CH4O3S.Pd/c1-23(2)26-21-29(24(3)4)33(30(22-26)25(5)6)34-31(36-7)19-20-32(37-8)35(34)38(27-15-11-9-12-16-27)28-17-13-10-14-18-28;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h19-25,27-28H,9-18H2,1-8H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

Clé InChI

PQYBJDCHLVJYSD-UHFFFAOYSA-M

Catégories apparentées

Description générale

BrettPhos Pd G3 is a third generation (G3) Buchwald precatalyst. It is air, moisture and thermally-stable and is highly soluble in a wide range of common organic solvents. It has long life in solutions. BrettPhos Pd G3 is an excellent reagent for Buchwald-Hartwig cross-coupling reaction. Some of its unique features include lower catalyst loadings, shorter reaction time, efficient formation of the active catalytic species and accurate control of ligand: palladium ratio.

Application

BrettPhos Pd G3 may be used for the C-N coupling reaction between monosubstituted ureas and 1,2 dihaloaromatic system to form benzimidazolones.
It may be used in the synthesis of following compounds:
  • [Pd(cinnamyl)(BrettPhos)]OTf by reacting with [(cinnamyl)PdCl]2 and AgOTf.
  • [Pd(crotyl)(BrettPhos)]OTf by reacting with [(crotyl)PdCl]2 and AgOTf.
  • [Pd(allyl)(BrettPhos)]OTf by reacting with [(allyl)PdCl]2 and AgOTf.
  • Pd(allyl)(BrettPhos)Clby reacting with [(allyl)PdCl]2.
For small scale and high throughput uses, product is also available as ChemBeads (928321)

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000397370
0000397370
0000279695
SHBS0862
SHBR9689

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Consulter la Bibliothèque de documents

Regioselective Synthesis of Benzimidazolones via Cascade C-N Coupling of Monosubstituted Ureas.
Ernst JB, et al.
Organic Letters, 16(14), 3844-3846 (2014)
Generating Active ?L-Pd (0)? via Neutral or Cationic Π-Allylpalladium Complexes Featuring Biaryl/Bipyrazolylphosphines: Synthetic, Mechanistic, and Structure-Activity Studies in Challenging Cross-Coupling Reactions.
DeAngelis AJ, et al.
The Journal of Organic Chemistry, 80(13), 6794-6813 (2015)
2-Aminobiphenyl Palladacycles: The ?Most Powerful? Precatalysts in C-C and C-Heteroatom Cross-Couplings.
Bruneau A, et al.
ACS Catalysis, 5(2), 1386-1396 (2015)

Articles

Scale-Up Guide: Buchwald-Hartwig Amination

Preformed catalysts in the kit are stable but become air-sensitive when activated; Schlenk technique aids scale-up.

Scale-Up Guide: Buchwald-Hartwig Amination

Preformed catalysts in the kit are stable but become air-sensitive when activated; Schlenk technique aids scale-up.

Scale-Up Guide: Buchwald-Hartwig Amination

Preformed catalysts in the kit are stable but become air-sensitive when activated; Schlenk technique aids scale-up.

Scale-Up Guide: Buchwald-Hartwig Amination

Preformed catalysts in the kit are stable but become air-sensitive when activated; Schlenk technique aids scale-up.

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Contenu apparenté

Buchwald Group – Professor Product Portal

The Buchwald group has developed a series of highly active and versatile palladium precatalysts and biarylphosphine ligands used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. The ligands are electron-rich, and highly tunable to provide catalyst systems with a diverse scope, high stability and reactivity. Furthermore, the new series of precatalysts are air-, moisture and thermally-stable and display good solubility in common organic solvents. The use of precatalysts ensures the efficient generation of the active catalytic species and allows one to accurately adjust the ligand:palladium ratio. The ligands, precatalysts and methodology developed in the Buchwald group are user friendly and have rendered previously difficult cross couplings reactions, much easier to achieve.

Buchwald and non-Buchwald catalysts and ligands for pharma or industrial chemistry applications

Explore reliable, premium grade catalysis materials for your pharma or industrial project. Specialty chemicals and formulations are available in bulk quantities and volumes from a few grams to multi-metric tons with complete documentation to simplify your leap from development to commercialization.

Buchwald and non-Buchwald catalysts and ligands for pharma or industrial chemistry applications

Explore reliable, premium grade catalysis materials for your pharma or industrial project. Specialty chemicals and formulations are available in bulk quantities and volumes from a few grams to multi-metric tons with complete documentation to simplify your leap from development to commercialization.

Buchwald and non-Buchwald catalysts and ligands for pharma or industrial chemistry applications

Explore reliable, premium grade catalysis materials for your pharma or industrial project. Specialty chemicals and formulations are available in bulk quantities and volumes from a few grams to multi-metric tons with complete documentation to simplify your leap from development to commercialization.

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