915299-24-0

Basic information

• Product Name: [Tris(2,4-di-tert-butylphenyl)phosphite]gold chloride
• Synonyms: [Tris(2,4-di-tert-butylphenyl)phosphite]gold chloride;Chloro[tris(2,4-di-tert-butylphenyl)phosphite]gold
• CAS NO: 915299-24-0
• Molecular Formula: C₄₂H₆₃AuClO₃P
• Molecular Weight: 880.36
• Product Categories: Au
• Mol File: 915299-24-0.mol

Chemical Properties

• Melting Point: 200-202 °C
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: [Tris(2,4-di-tert-butylphenyl)phosphite]gold chloride(CAS DataBase Reference)
• NIST Chemistry Reference: [Tris(2,4-di-tert-butylphenyl)phosphite]gold chloride(915299-24-0)
• EPA Substance Registry System: [Tris(2,4-di-tert-butylphenyl)phosphite]gold chloride(915299-24-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 915299-24-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
[Tris(2,4-di-tert-butylphenyl)phosphite]gold chloride is used as a catalyst for promoting efficient and selective chemical transformations in organic synthesis, due to its enhanced reactivity and selectivity provided by the steric protection of the ligand.
Used in Metal-Catalyzed Reactions:
In the field of metal-catalyzed reactions, [Tris(2,4-di-tert-butylphenyl)phosphite]gold chloride is utilized as a reagent, facilitating electron transfer and contributing to the success of various redox reactions.
Used in Industrial Applications:
[Tris(2,4-di-tert-butylphenyl)phosphite]gold chloride is employed in various industrial settings where its catalytic properties are leveraged to improve the efficiency and selectivity of chemical processes, thus enhancing the overall productivity and quality of the end products.
Used in Laboratory Research:
[Tris(2,4-di-tert-butylphenyl)phosphite]gold chloride is also used in laboratory research as a catalyst and reagent, enabling scientists to explore new chemical pathways and develop innovative synthetic methods.

Upstream product

• 39929-21-0 (tetrahydrothiophene)gold(I) chloride 
• 31570-04-4 tris(2,4-di-tert-butylphenyl)phosphite 
• 29892-37-3 chloro(dimethylsulfide) gold(I) 
• 4235-89-6 tris(4-(tert-butyl)phenyl) phosphite 

Relevant articles and documents

Taming gold(I)-counterion interplay in the de-aromatization of indoles with allenamides

A careful interplay between the π electrophilicity of a cationic Au I center and the basicity of the corresponding counterion allowed for the chemo- and regioselective inter- as well as intramolecular de-aromatization of 2,3-disubstituted indoles with allenamides. The silver-free bifunctional Lewis acid/Bronsted base complex [{2,4-(tBu)2C 6H3O}3PAuTFA] assisted the formation of a range of densely functionalized indolenines under mild conditions.

1,1-Phosphaboration of CC and CC bonds at gold

The phosphine-borane iPr2P(o-C6H4)BFXyl2 (Fxyl = 3,5-(F3C)2C6H3) was found to react with gold(i) alkynyl and vinyl complexes via an original 1,1-phosphaboration process. Zwitterionic complexes resulting from Au to B transmetallation have been authenticated as key intermediates. X-ray diffraction analyses show that the alkynyl-borate moiety remains pendant while the vinyl-borate is side-on coordinated to gold. According to DFT calculations, the phosphaboration then proceeds in a trans stepwise manner via decoordination of the phosphine, followed by anti nucleophilic attack to the π-CC bond activated by gold. The boron center acts as a relay and tether for the organic group. This journal is

Gold(I)-Catalyzed and Nucleophile-Guided Ligand-Directed Divergent Synthesis

Transition metal catalysts can mediate a plethora of skeleton rearrangements of a range of substrates to construct complex small molecules. Yet, their potential to transform common substrates into distinct molecular scaffolds has not been fully explored to deliver biologically relevant small molecules. Gold(I)-catalyzed transformations of enynes are amongst the most intriguing rearrangements and provide opportunities to access a range of diverse scaffolds efficiently. In ligand-directed divergent synthesis (LDS), variation of ligands in metal complexes determines the fate of substrates during their transformation into distinct scaffolds. For instance, variation of ligands for the gold(I) catalysts helps to transform oxindole derived 1,6-enynes into several distinct molecular frameworks. In this report, we present how ligand variation in gold(I) catalysts, nucleophile-additives and alkyl and alkynyl substitutions on the 1,6-enynes as well as replacement of the oxindole ring with a different privileged ring-system (PRS) influence the LDS approach to access a wider chemical space. Based on the experimental results, we propose several mechanistic pathways in gold(I)-catalyzed cycloisomerizations and cascade reactions of 1,6-enyne substrates leading to structurally distinct chemotypes.

Building polycyclic indole scaffolds via gold(I)-catalyzed intra- and inter-molecular cyclization reactions of 1,6-enynes

A gold(I) catalyzed cycloisomerization of indolyl-1,6-enynes via 5-exo-dig cyclization is reported. The reaction passes through an intermediate whose fate can be steered to yield different indole polycyclic scaffolds through various intra- and inter-molecular cyclization reactions. One of the key transformations of indolyl-1,6-enynes was a formal [2+2+2] cycloaddition reaction with various aldehydes to afford natural product-like tetracyclic indoles.

Efficient general procedure to access a diversity of gold(0) particles and gold(I) phosphine complexes from a simple HAuCl4 source. Localization of homogeneous/heterogeneous system's interface and field-emission scanning electron microscopy study

Soluble gold precatalysts, aimed for homogeneous catalysis, under certain conditions may form nanoparticles, which dramatically change the mechanism and initiate different chemistry. The present study addresses the question of designing gold catalysts, taking into account possible interconversions and contamination at the homogeneous/heterogeneous system's interface. It was revealed that accurate localization of boundary experimental conditions for formation of molecular gold complexes in solution versus nucleation and growth of gold particles opens new opportunities for well-known gold chemistry. Within the developed concept, a series of practical procedures was created for efficient synthesis of soluble gold complexes with various phosphine ligands (R3P)AuCl (90-99% yield) and for preparation of different types of gold materials. The effect of the ligand on the particles growth in solution has been observed and characterized with high-resolution field-emission scanning electron microscopy (FE-SEM) study. Two unique types of nanostructured gold materials were prepared: hierarchical agglomerates and gold mirror composed of ultrafine smoothly shaped particles.