1447963-75-8

Basic information

• Product Name: tBuXPhos Pd G3
• Synonyms: Methanesulfonato(2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-aMino-1,1'-biphenyl-2-yl)palladiuM(II), Min. 98% [t-BuXPhos Palladacycle];tBuXPhos Pd G3;Methanesulfonato(2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II);[(2-Di-tert-butylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate;tBuXPhos Pd G3 97%;[2'-(Amino)[1,1'-biphenyl]-2-yl][bis(1,1-dimethylethyl)[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium;Methanesulfonato(2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II), min. 98%;Palladium, [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][bis(1,1-dimethylethyl)[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato-κO)-
• CAS NO: 1447963-75-8
• Molecular Formula: C42H58NO3PPdS
• Molecular Weight: 794.38
• Product Categories: Buchwald Ligands&Precatalysts;Buchwald Precatalysts Series;Pd
• Mol File: 1447963-75-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 130-140°C
• Appearance: yellow/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: tBuXPhos Pd G3(CAS DataBase Reference)
• NIST Chemistry Reference: tBuXPhos Pd G3(1447963-75-8)
• EPA Substance Registry System: tBuXPhos Pd G3(1447963-75-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1447963-75-8(Hazardous Substances Data)

Usage

Description

tBuXPhos Pd G3, a third-generation Buchwald precatalyst, is an air, moisture, and thermally-stable dark grey crystalline powder. It is highly soluble in a wide range of common organic solvents and has a long life in solutions. This precatalyst is an excellent reagent for Buchwald-Hartwig cross-coupling reactions, offering 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 Pharmaceutical Industry:
tBuXPhos Pd G3 is used as a catalyst for the synthesis of various pharmaceutical compounds. Its application reason is its ability to facilitate Buchwald-Hartwig cross-coupling reactions, which are crucial in the production of complex molecular structures found in many drugs.
Used in Chemical Synthesis:
tBuXPhos Pd G3 is used as a catalyst for cyanation reactions, such as the synthesis of 4-cyano-7-azaindole from 4-chloro-7-azaindole. Its application reason is its efficiency in promoting the reaction under mild conditions, leading to the desired product with high yield.
Used in Organic Chemistry Research:
tBuXPhos Pd G3 is used as a catalyst for α-arylation reactions of acetate esters at room temperature. Its application reason is its ability to lower the reaction temperature, thus reducing energy consumption and side reactions, and improving the overall yield of the desired product.

Reaction

Mild palladium-catalyzed cyanation of (hetero)aryl halides and triflates in aqueous media.

Storage

tBuXPhos Pd G3 should be stored in an airtight, dry and low temperature.

Upstream product

• 1435520-65-2 (2'-amino-1,1'-biphenyl-2-yl)methanesulfonatopalladium(II) dimer 
• 564483-19-8 tert-butyl XPhos 

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.