14243-64-2

Usage

Uses

Used in Gold Chemistry:
Chloro(triphenylphosphine)gold is used as a catalyst for various rearrangement reactions in organic synthesis, facilitating the formation of complex organic molecules.
Used in Pharmaceutical Industry:
Chloro(triphenylphosphine)gold is used as a precursor for the synthesis of gold(I) and gold(III) organometallic compounds, which have potential applications in the development of pharmaceuticals and drug delivery systems.
Used in Organic Synthesis:
Chloro(triphenylphosphine)gold is used as a catalyst in the cyclization of O-propargyl carbamates to alkylideneoxazolidinones via a 5-exo-digonal pathway at room temperature, enabling the formation of complex cyclic structures.
Used in Material Science:
Chloro(triphenylphosphine)gold is used as a catalyst in the cycloisomerization of enynes containing a cyclic olefin into highly-fused, polycyclic dienes at room temperature, which can be useful in the development of advanced materials with specific properties.

InChI:InChI=1/C18H15P.Au.ClH/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;/h1-15H;;1H/q;+1;/p-1

Upstream product

• 69462-32-4 cloro(thiodiethanol)gold(I) 
• 603-35-0 triphenylphosphine 
• 64345-29-5 [Pd2Cl2(μ-bis(diphenylphosphino)methane)2] 
• 7647-01-0 hydrogenchloride 
• 207515-11-5 (C₁₆H₁₂ClN₂O)Au(P(C₆H₅)3) 
• 333958-10-4 [Au(methyl acetimino)(PPh₃)]TfO 
• 690229-26-6 chloro(2-(azidomethyl)phenyl isocyanide)gold(I) 
• 29892-37-3 chloro(dimethylsulfide) gold(I) 
• 39929-21-0 (tetrahydrothiophene)gold(I) chloride 
• 15189-51-2 sodium tetrachloroaurate(III) 

Downstream Products

• 850513-39-2 cis-dimethyl(ethynyl)(triphenylphosphine)gold(III) 
• 908863-38-7 Ph₃PMe[HCCAuCCH] 

Relevant academic research and scientific papers

[Au3Ge18]5 - A gold-germanium cluster with remarkable Au-Au interactions

Gold linkers: The first soluble gold-germanium cluster was obtained from the reaction of [Au(PPh3)Cl] and K4Ge9. The formation of the gold complex [Ge9Au3Ge9] 5- (see picture) shows also an exciting result for gold chemistry: linearly coordinated gold atoms and the characteristics of aurophilic contacts between the metal atoms can be observed in the presence of polyanionic Zintl ions. (Figure Presented).

Bis1N'>gold(III) Complexes. Crystal and Molecular Structure of Bis1N'>gold(III) Tetrachloroaurate

The reaction between and gave the gold(III) complex which reacts with AgClO4 to form ClO4.Addition of X (X=Cl), NaX (X=Br), or KX (X=I, CN or O2CMe), to the cationic complex leads to the corresponding neutral complexes .Reaction of ClO4 with -, leads to .By reacting the neutral acetato-complex with ClO4 (Hpy=pyridinium), ClO4 is prepared.The crystal structure of has been determined and shows that the cation has a square-planar co-ordination with two cis-nitrogen and the two cis-carbon atoms bonded to gold.

Gold(I)-phosphine-N-heterocycles: Biological activity and specific (ligand) interactions on the C-terminal HIVNCp7 zinc finger

The syntheses and the characterization by chemical analysis, 1H and 31P NMR spectroscopy, and mass spectrometry of a series of linear triphenylphosphine gold(I) complexes with substituted N-heterocycle ligands (L), [(PPh3)Au(I)(L)]+, is reported. The reaction of [(PPh3)Au(L)]+ (L = Cl- or substituted N- heterocyclic pyridine) with the C-terminal (Cys3His) finger of HIVNCp7 shows evidence by mass spectrometry (ESI-MS) and 31P NMR spectroscopy of a long-lived {(PPh3)Au}-S-peptide species resulting from displacement of the chloride or pyridine ligand by zinc-bound cysteine with concomitant displacement of Zn2+. In contrast, reactions with the Cys2His2 finger-3 of the Sp1 transcription factor shows significantly reduced intensities of {(PPh3)Au} adducts. The results suggest the possibility of systematic (electronic, steric) variations of carrier group PR3 and leaving group L as well as the nature of the zinc finger in modulation of biological activity. The cytotoxicity, cell cycle signaling effects, and cellular accumulation of the series are also reported. All compounds display cytotoxicity in the micromolar range upon 96 h continuous exposure to human tumor cells. The results may have relevance for the reported inhibition of viral load in simian virus by the gold(I) drug auranofin.

Dynamic covalent assembly and disassembly of nanoparticle aggregates

The quantitative assembly and disassembly of a new type of dynamic covalent nanoparticle (NP) building block is reported. In situ spectroscopic characterization reveals constitutionally adaptive NP-bound monolayers of boronate esters. Ditopic linker molecules are used to produce covalently connected AuNP assemblies, displaying open dendritic morphologies, and which, despite being linked by covalent bonds, can be fully disassembled on application of an appropriate chemical stimulus.

Synthesis, crystal structure and a spectroscopic study of bis(triphenylphosphine)gold(I)+ TCNQ-

The complex of the bis(triphenylphosphine)gold(I) cation and the radical anion of 2,2-(2,5-cyclohexadiene-1,4-diylidene)bispropanedinitrile, (TCNQ), has been prepared and characterized by spectroscopic and X-ray crystallographic methods. The solid state structure consists of the linear (P-Au-P) cation bis(triphenylphosphine)gold(I) and the approximately planar radical anion of TCNQ. The bond lengths are: Au-P 2.300(2); P-C 1.800(11), 1.789(11), 1.800(11); C≡N 1.175(16), 1.128(16). The infrared spectrum of the complex exhibits bands at 2176 and 2150 cm-1 in the nitrile region. The electron spin resonance spectrum of this compound, in benzene, is consistent with a structure in which the TCNQ radical anion is symmetrically oriented about the bis(triphenylphosphine)gold(I) cation. The hyperfine coupling constants are: aN = 0.981, aH = 1.379, aP = 0.095 gauss.

Gold nanoparticles on wool in a comparative study with molecular gold catalysts

The catalytic activity of gold chloride nanoparticles is compared to the activity of two molecular gold(I) chloride phosphine complexes for the addition of methanol to 3-hexyne. The phosphines are triphenylphosphine and the bispidinone related bulky 6,8-bis-(4-dimethylamino-phenyl)-3-methyl-9-oxo-7- phenyl-3-aza-7-phospha-bicyclo[3.3.1]nonan-1,5-dicarboxylic acid dimethyl ester. Use of the bulky ligand made the addition reaction selective towards the enol product, meaning that no addition of methanol or water to alkenes, which were produced during the reaction, occurred. In contrast, use of triphenylphosphine gold(I) chloride resulted in the synthesis of a variety of products. The phosphines decomposed during reaction leading to the formation of gold nanoparticles, which were found to be catalytically inactive. Artificially produced gold nanoparticles also proved to be inactive. In contrast, gold chloride nanoparticles deposited on wool were active comparable to the gold phosphine-containing catalysts tested previously. Overall activities observed were low compared to results from the literature suggesting that the operating conditions chosen could be optimised.

Synthesis and reactivity of [Au(2-CH2-6-RC5H3N)(PPh3)] (R = H, Me). X-ray structure of [Ag{Au(2-CH2-6-MeC5H3N)(PPh3)} 2][ClO4]

The reaction of Li(2-CH2-6-RC5H3N) with [AuCl(PPh3)] leads to the mononuclear complexes [Au(2-CH2-6-RC5H3N)(PPh3)] (R = H, Me). These react further with other copper, silver or gold compounds to give heteronuclear derivatives, [M{Au(2-CH2-6-RC5H3N)(PPh3)} 2][X] (M = Cu, X = PF6 or M = Ag, X = ClO4), or the dinuclear complex [Au(2-CH2-6-MeC5H3N)]2. The crystal structure of [Ag{Au(2-CH2-6-MeC5H3N)(PPh3)} 2][ClO4] has been determined by X-ray diffraction studies and shows short interactions between the gold and silver centres.

SYNTHESIS OF ORGANOGOLD(1+) COMPOUNDS BY DIRECT AURATION

Organogold(1+) compounds have been synthesized by direct auration of cyclopentadiene, cyanoacetic ester and malonitrile with (Ph3PAu)3O+BF4-.An X-ray structural study (λ Mo, 5062 reflections, R = 0.039) of bis(triphenylphosphinegold)malonitrile has been carried out (monoclinic, a = 12.055(6), b = 14.086(5), c = 20.466(12) Angstroem, β = 90.32(4) deg, space group P21/c, Z = 4).The Au-Au bond length is 2.912(1) Angstroem.

Fibrous nano-silica containing immobilized Ni@Au core-shell nanoparticles: A highly active and reusable catalyst for the reduction of 4-nitrophenol and 2-nitroaniline

A novel, dandelion-like fibrous nano-silica catalyst (Ni@Au/KCC-1) has been synthesized by modifying fibrous nano-silica (KCC-1) with Ni@Au core-shell nanoparticles (NPs). KCC-1 was prepared using a hydrothermal method and has a dandelion-like shape, high surface area, and easy accessibility; KCC-1 can also be functionalized with 3-mercaptopropyltriethoxysilane. The mercaptopropyl groups on the fibers act as robust anchors for the immobilization of Ni@Au NPs, thus preventing the aggregation of the Ni@Au NPs. We investigated the catalytic performance of the Ni@Au/KCC-1 nanocatalyst by reducing 4-nitrophenol to 4-aminophenol in the presence of NaBH4 as a probe reaction. The resulting Ni@Au/KCC-1 nanocatalyst exhibited superior catalytic activity to Ni@Au NPs, which may be attributed to the high accessibility of the KCC-1 support material. To some extent, it also may be due to the poor aggregation of Ni@Au NPs on the KCC-1 nano-silica support. The Ni@Au/KCC-1 nanocatalyst also showed high catalytic activity when used to reduce 2-nitroaniline. It is noteworthy that using Ni cores to fabricate the active sites Ni@Au NPs resulted in a lower amount of Au needed than is typical, because most of the Au-NPs catalyzed reactions occur on the surfaces of the NPs. In addition, the Ni cores give the Ni@Au/KCC-1 nanocatalyst superparamagnetic properties that increase its ease of recovery by a powerful magnet, allowing for it to be reused. The abovementioned approach based on fibrous KCC-1 and Ni@Au NPs provided a useful platform for the fabrication of noble-metal-based nanocatalysts with easy accessibility and a low cost, which may allow for an efficient green alternative for various catalytic reductions.

Thiol-functionalized undecagold clusters by ligand exchange: Synthesis, mechanism, and properties

Ligand exchange of phosphine-stabilized undecagold precursor particles, Au11(PPh3)8Cl3, with ω-functionalized thiols provides a convenient and general approach for the rapid preparation of large families of thiol-stabilized, subnanometer (d CORE ～ 0.8 nm) particles. The approach permits rapid incorporation of specific functionality into the stabilizing ligand shell, is tolerant of a wide range of functional groups, and provides convenient access to new materials inaccessible by other methods. Mechanistic studies and trapping experiments give insight into the progression of the ligand exchange, providing evidence that the core size of the phosphine-stabilized undecagold precursor particles is preserved during ligand exchange. The optical properties of the thiol-stabilized nanoparticles depend strongly on the composition of the ligand shell, and a series of studies suggests that this dependence is a result of the ligand shell's influence on the electronic structure of the particle core, as opposed to a structural change within the nanoparticle core.