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763403

Sigma-Aldrich

RuPhos Pd G3

98%

Synonyme(s) :

(2-Dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate, RuPhos-G3-Palladacycle, RuPhos-Pd-G3

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About This Item

Formule empirique (notation de Hill):
C43H56NO5PPdS
Numéro CAS:
Poids moléculaire :
836.37
Numéro MDL:
Code UNSPSC :
12161600
ID de substance PubChem :
Nomenclature NACRES :
NA.22

Pureté

98%

Forme

solid

Caractéristiques

generation 3

Pertinence de la réaction

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

Capacité de réaction

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

Pf

188-196 °C (decomposition)

Groupe fonctionnel

phosphine

Chaîne SMILES 

CS(=O)(=O)O[Pd]c1ccccc1-c2ccccc2N.CC(C)Oc3cccc(OC(C)C)c3-c4ccccc4P(C5CCCCC5)C6CCCCC6

InChI

1S/C30H43O2P.C12H10N.CH4O3S.Pd/c1-22(2)31-27-19-13-20-28(32-23(3)4)30(27)26-18-11-12-21-29(26)33(24-14-7-5-8-15-24)25-16-9-6-10-17-25;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h11-13,18-25H,5-10,14-17H2,1-4H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

Clé InChI

AXZLIMCJMPNFFU-UHFFFAOYSA-M

Description générale

RuPhos Pd G3 is a third generation (G3) Buchwald precatalyst that can be used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. It is air-, moisture-, and thermally-stable and is highly soluble in a wide range of common organic solvents. 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

RuPhos Pd G3 can be used as a pre-catalyst in the following protocols:
  • Palladium-catalyzed Suzuki coupling of 5-p-toluenesulfonyltetrazoles with arylboronic acids to synthesize 1,5-disubstituted tetrazoles.
  • Suzuki-Miyaura catalyst-transfer polycondensation (SCTP) of 3-alkylthiophenes in the presence of N-methylimidodiacetic (MIDA)-boronate monomers.
  • Suzuki-Miyaura-cross-coupling of aminothiophenes.
For small scale and high throughput uses, product is also available as ChemBeads (928283)

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

Aquatic Chronic 3 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

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


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

3-Cyanoallyl boronates are versatile building blocks in the synthesis of polysubstituted thiophenes.
Shao W, et al.
Chemical Science, 8(6), 4431-4436 (2017)
A Rational Design of Highly Controlled Suzuki-Miyaura Catalyst-Transfer Polycondensation for Precision Synthesis of Polythiophenes and their Block Copolymers: Marriage of Palladacycle Precatalysts with MIDA-boronates.
Seo KB, et al.
Journal of the American Chemical Society (2018)
Preparation of highly functionalized 1, 5-disubstituted tetrazoles via palladium-catalyzed Suzuki coupling.
Hennessy EJ, et al.
Tetrahedron Letters, 58(17), 1709-1713 (2017)

Articles

G3 and G4 Buchwald palladium precatalysts are the newest air, moisture, and thermally stable crossing-coupling complexes used in bond formation for their versatility and high reactivity.

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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.

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.

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.

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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