49763-41-9

Basic information

• Product Name: Chloro(tricyclohexylphosphine)gold(I)
• Synonyms: Chloro(tricyclohexylphosphine)gold(I)
• CAS NO: 49763-41-9
• Molecular Formula: C₁₈H₃₃AuClP
• Molecular Weight: 512
• Mol File: 49763-41-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 218-222°C
• Appearance: /
• CAS DataBase Reference: Chloro(tricyclohexylphosphine)gold(I)(CAS DataBase Reference)
• NIST Chemistry Reference: Chloro(tricyclohexylphosphine)gold(I)(49763-41-9)
• EPA Substance Registry System: Chloro(tricyclohexylphosphine)gold(I)(49763-41-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-26-45
• WGK Germany: 3
• Hazardous Substances Data: 49763-41-9(Hazardous Substances Data)

Usage

Uses

Catalyst for:Formal tandem bicyclizations of styrylindoles with alkynyl alkenonesAddition of X-H bonds to carbon-carbon multiple bondsArylation of pyrazine or pyridine with aryl bromidesHydroarylation of alkenes with indolesCyclizationHydroamination

Upstream product

• 98938-44-4 5.6-μ-(AuPCy3)-nido-B10H13 
• 7647-01-0 hydrogenchloride 
• 7440-57-5 gold 
• 2622-14-2 tricyclohexylphosphine 
• 39929-21-0 (tetrahydrothiophene)gold(I) chloride 
• 932-72-9 (Dichloroiodo)benzene 
• 64-17-5 ethanol 
• 1190715-83-3 [AuCl₃(P(C₆H₁₁)3)] 
• 29892-37-3 chloro(dimethylsulfide) gold(I) 

Downstream Products

• 199167-50-5 Au(-C*C-(t)Bu)(PCy₃) 
• 199167-49-2 Au(-C*C-SiMe₃)(PCy₃) 
• 408495-43-2 [(tricyclohexylphosphine)Au](μ-CC-1,4-C6H4CC) 
• 587023-06-1 (thiourea-κS)(tricyclohexylphosphine)gold(I) chloride 
• 909421-57-4 (gold(I)2(pyridyl-2,6-diphenyl)(P(cyclohexyl))3 
• 939785-15-6 [Pt((2,7-di-tert-butylfluoren-9-ylidene)methanedithiolato)2(Au(PCy₃))2] 
• 939785-13-4 [Pd((2,7-di-tert-butylfluoren-9-ylidene)methanedithiolato)2(Au(PCy₃))2] 
• 1094064-62-6 ((C₆H₁₁)3P)AuC₄O₂(C₆H₁₃)(H)(CH₃) 
• 49763-42-0 (tricyclohexylphosphine)gold(I) bromide 
• 1231960-32-9 Cy₃PAu-CC-(CH=CH)2-CC-AuPCy₃ 
• 1231960-33-0 Cy₃PAu-CC-(CH=CH)3-CC-AuPCy₃ 
• 1231960-36-3 Cy₃PAu-CC-1,2-di(2-methylthien-3-yl)hexafluorocyclopentene-CC-AuPCy₃ 

Relevant articles and documents

Dinuclear Au(I), Au(II) and Au(III) Complexes with (CF2)n Chains: Insights into The Role of Aurophilic Interactions in the Au(I) Oxidation

New dinuclear Au(I), Au(II) and Au(III) complexes containing (CF2)n bridging chains were obtained. Metallomacrocycles [Au2{μ-(CF2)4}{μ-diphosphine}] show an uncommon figure-eight structure, the helicity inversion barrier of which is influenced by aurophilic interactions and steric constraints imposed by the diphosphine. Halogenation of LAu(CF2)4AuL (L=PPh3, PMe3, (dppf)1/2, (binap)1/2) gave [Au(II)]2 species, some of which display unprecedented folded structures with Au?Au bonds. Aurophilic interactions facilitate this oxidation process by preorganizing the starting [Au(I)]2 complexes and lowering its redox potential. The obtained [Au(II)]2 complexes undergo thermal or photochemical elimination of R3PAuX to give Au(III) perfluorinated auracycles. Evidence of a radical mechanism for these decomposition reactions was obtained.

Gold(I) complexes with chloro(diaryl)silyl ligand. Stoichiometric reactions and catalysis for O-functionalization of organosilane

An Au(I) complex with a chloro(diphenyl)silyl ligand [Au(SiPh2Cl)(PCy3)] (1a) is obtained from the reaction of Ph2SiH2 with [AuCl(PCy3)]. (4-FC6H4)2SiH2, (4-MeC6H4)2SiH2, and Ph2GeH2 react with [AuCl(PCy3)] to form complexes with the chlorodiarylsilyl ligand, [Au(SiAr2Cl)(PCy3)] (1b: Ar = C6H4-4-F, 1c: Ar = C6H4-4-Me) and with the chloro(diphenyl)germyl ligand, [Au(GePh2Cl)(PCy3)] (2a), respectively. Complex 1a reacts with H2O to form Ph2SiH(OH) and (Ph2SiH)2O, whereas the reaction of EtOH with 1a yields Ph2SiH(OEt) exclusively. Complex 1a catalyzes the hydrolysis of Ph2SiH2 ([Au]:[H2SiPh2]:[H2O] = 0.05:1.0:10.0) at 60 °C to yield Ph2SiH(OH) and (Ph2SiH)2O. The reaction of Ph2SiH2 with HOEt in the presence of a catalytic amount of 1a affords Ph2SiH(OEt). Both stoichiometric and catalytic reactions using 1a lead to the recovery of [AuCl(PCy3)] from the reaction mixture.

C(sp2)-C(sp2) Reductive Elimination from Well-Defined Diarylgold(III) Complexes

A series of well-defined phosphine-ligated diarylgold(III) complexes cis-[Au(L)(ArF)(Ar′)(Cl)] were prepared, and detailed kinetics of the C(sp2)-C(sp2) reductive elimination from these complexes were studied. The mechanism of the reductive elimination from the complexes cis-[Au(L)(ArF)(Ar′)(Cl)] was further studied by theoretical calculations. The combination of experimental and theoretical results suggests that the biaryl reductive elimination from organogold(III) complexes cis-[Au(L)(ArF)(Ar′)(Cl)] proceeds through a concerted biaryl-forming pathway from the four-coordinated Au(III) metal center. These studies also disclose that the steric hindrance of the phosphine ligands plays a major role in promoting the biaryl-forming reductive elimination from diarylgold(III) complexes cis-[Au(L)(ArF)(Ar′)(Cl)], while electronic properties of these ligands have a much smaller effect. Futhermore, it was found that the complexes with more weakly electron withdrawing aryl ligands undergo reductive elimination more quickly and the elimination rate is not sensitive to the polarity of the solvents.