1445085-77-7

Basic information

• Product Name: RuPhos Pd G3
• Synonyms: Methanesulfonato(2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl)(2'-aMino-1,1'-biphenyl-2-yl)palladiuM(II), Min. 98% [RuPhos Palladacycle];Methanesulfonato(2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl)(2'-aMino-1,1'-biphenyl-2-yl)palladiuM(II), Min. 98%;RuPhos Pd G3 95%;Methanesulfonato(2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II);(2-Dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate;RuPhos Pd G3;RuPhos-G3-Palladacycle;RuPhos-Pd-G3
• CAS NO: 1445085-77-7
• Molecular Formula: C₁₃H₁₃NO₃PdS*C₃₀H₄₃O₂P
• Molecular Weight: 837.375141
• Product Categories: Buchwald Ligands&Precatalysts;Buchwald Precatalysts Series;Pd
• Mol File: 1445085-77-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 188-196°C (decomposition)
• Appearance: white/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: RuPhos Pd G3(CAS DataBase Reference)
• NIST Chemistry Reference: RuPhos Pd G3(1445085-77-7)
• EPA Substance Registry System: RuPhos Pd G3(1445085-77-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-52/53
• Safety Statements: 26-61
• WGK Germany: 3
• Hazardous Substances Data: 1445085-77-7(Hazardous Substances Data)

Usage

Description

RuPhos Pd G3 is a third-generation (G3) Buchwald precatalyst designed for cross-coupling reactions, which is air-, moisture-, and thermally-stable. It is highly soluble in a wide range of common organic solvents and offers unique features such as lower catalyst loadings, shorter reaction times, efficient formation of the active catalytic species, and accurate control of the ligand: palladium ratio.

Uses

Used in Chemical Synthesis:
RuPhos Pd G3 is used as a pre-catalyst for the formation of various chemical bonds, including C-C, C–N, C–O, C–F, C–CF3, and C–S bonds, in cross-coupling reactions.
Used in Pharmaceutical Industry:
RuPhos Pd G3 is used as a pre-catalyst for the synthesis of complex molecules and pharmaceutical compounds, enabling the formation of multiple types of chemical bonds, which is crucial for the development of new drugs.
Used in Suzuki Coupling Reactions:
RuPhos Pd G3 is used as a pre-catalyst in the Suzuki coupling of 5-p-toluenesulfonyltetrazoles with arylboronic acids to synthesize 1,5-disubstituted tetrazoles.
Used in Suzuki-Miyaura Catalyst-Transfer Polycondensation (SCTP):
RuPhos Pd G3 is used as a pre-catalyst in the SCTP of 3-alkylthiophenes in the presence of N-methylimidodiacetic (MIDA)-boronate monomers.
Used in Suzuki-Miyaura Cross-Coupling:
RuPhos Pd G3 is used as a pre-catalyst in the Suzuki-Miyaura cross-coupling of aminothiophenes, which is essential for the synthesis of various organic compounds and materials.

Reaction

Palladium catalyst used for facile, C-N cross-coupling reactions. A practical synthesis of indoles via a Pd-catalyzed C-N ring formation.

Upstream product

• 1435520-65-2 (2'-amino-1,1'-biphenyl-2-yl)methanesulfonatopalladium(II) dimer 
• 787618-22-8 ruphos 
• 1445085-50-6 [1,1'-biphenyl]-2-aminium methanesulfonate 
• 90-41-5 2-phenylaniline 

Relevant articles and documents

Design and preparation of new palladium precatalysts for C-C and C-N cross-coupling reactions

A series of easily prepared, phosphine-ligated palladium precatalysts based on the 2-aminobiphenyl scaffold have been prepared. The role of the precatalyst-associated labile halide (or pseudohalide) in the formation and stability of the palladacycle has been examined. It was found that replacing the chloride in the previous version of the precatalyst with a mesylate leads to a new class of precatalysts with improved solution stability and that are readily prepared from a wider range of phosphine ligands. The differences between the previous version of precatalyst and that reported here are explored. In addition, the reactivity of the latter is examined in a range of C-C and C-N bond forming reactions.