854045-94-6

Basic information

• Product Name: 2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISO&
• Synonyms: 2-Dicyclohexylphosphino-2μ,4μ,6μ-triisopropylbiphenyl gold(I) chloride;Chloro[2-dicyclohexyl(2μ,4μ,6μ-trisopropylbiphenyl)phosphine]gold(I);XPhos AuCl;Gold,chloro[dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine]-;6′Chloro[2-dicyclohexyl(2′-trisopropylbiphenyl)phosphine]gold(I);dicyclohexyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane:gold(1+):chloride
• CAS NO: 854045-94-6
• Molecular Formula: C₃₃H₄₉AuClP
• Molecular Weight: 709.147
• Product Categories: Au
• Mol File: 854045-94-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 243-250 °C
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISO&(CAS DataBase Reference)
• NIST Chemistry Reference: 2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISO&(854045-94-6)
• EPA Substance Registry System: 2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISO&(854045-94-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 854045-94-6(Hazardous Substances Data)

Usage

Uses

Catalyst for: Michael addition and intramolecular hydroalkylation reactionsCascade cyclization of diynesHydroarylation of allenes via a highly regioselective carbon-carbon bond formation producing six-membered ringsAlkyne cyclizations in a Holey catalytic environment

Upstream product

• 29892-37-3 chloro(dimethylsulfide) gold(I) 
• 564483-18-7 XPhos 
• 39929-21-0 (tetrahydrothiophene)gold(I) chloride 

Downstream Products

• 1109286-82-9 [((2',4',6'-triisopropyl-2-biphenyl)dicyclohexylphosphine)Au(azide)] 
• 1428578-54-4 Au(Me)(Cy)2P(C₆H₄C₆H₂iPr₃) 
• 1509948-51-9 XPhosAu(triazole)OTf 
• 1509948-51-9 XPhosAu(1H-benzotriazole) triflate 
• 934506-10-2 2-(dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl Au bis(trifluoromethylsulfonyl)imide 
• 925253-64-1 [(PCy₂(2',4',6'-triisopropylbiphenyl)AuBr] 

Relevant articles and documents

Synthesis of Polysubstituted Fused Pyrroles by Gold-Catalyzed Cycloisomerization/1,2-Sulfonyl Migration of Yndiamides

Yndiamides (bis-N-substituted alkynes) are valuable precursors to azacycles. Here we report a cycloisomerization/1,2-sulfonyl migration of alkynyl-yndiamides to form tetrahydropyrrolopyrroles, unprecedented heterocyclic scaffolds that are relevant to medicinal chemistry. This functional group tolerant transformation can be achieved using Au(I) catalysis that proceeds at ambient temperature, and a thermally promoted process. The utility of the products is demonstrated by a range of reactions to functionalize the fused pyrrole core.

Human Serum Albumin-Delivered [Au(PEt3)]+ Is a Potent Inhibitor of T Cell Proliferation

Using a modular library format in conjunction with cell viability (MTS) and flow cytometry assays, 90 cationic complexes [AuPL]n+ (P = phosphine ligand; L = thiourea derivative or chloride) were studied for their antiproliferative activity in CD8+ T lymphocyte cells. The activity of the compounds correlates with the steric bulk of the phosphine ligands. Thiourea serves as a leaving group that is readily replaced by cysteine thiol (NMR, ESI-MS). Taking advantage of selective thiourea ligand exchange, the fragments [Au(PEt3)]+ and [Au(JohnPhos)]+ (JohnPhos = 1,1′-biphenyl-2-yl)di-tert-butylphosphine) in compounds 1 and 2 were transferred to recombinant human serum albumin (rHSA). PEt3 promoted efficient modification of Cys34 in HSA (HSA-1), whereas use of bulky JohnPhos as a carrier ligand led to serum protein nonspecifically modified with multiple gold adducts (HSA-2) (Ellman’s test, ESI-TOF MS). HSA-1, but not HSA-2, strongly inhibits T cell proliferation at nanomolar doses. The potential role of HSA as a delivery vehicle in gold-based autoimmune disease treatment is discussed.

Oxidative Addition to Gold(I) by Photoredox Catalysis: Straightforward Access to Diverse (C,N)-Cyclometalated Gold(III) Complexes

Herein, we report the oxidative addition of aryldiazonium salts to ligand-supported gold(I) complexes under visible light photoredox conditions. This method provides experimental evidence for the involvement of such a process in dual gold/photoredox-catalyzed reactions and delivers well-defined (C,N)-cyclometalated gold(III) species. The remarkably mild reaction conditions and the ability to widely vary the ancillary ligand make this method a potentially powerful synthetic tool to access diverse gold(III) complexes for systematic studies into their properties and reactivity. Initial studies show that these species can undergo chloride abstraction to afford Lewis acidic dicationic gold(III) species.