854045-94-6

Usage

Uses

Used in Catalyst for Michael addition:
2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISO& is used as a ligand in catalysts for Michael addition reactions, where it facilitates the addition of nucleophiles to α,β-unsaturated carbonyl compounds. Its steric and electronic properties contribute to the efficiency and selectivity of the reaction.
Used in Catalyst for intramolecular hydroalkylation:
In intramolecular hydroalkylation reactions, 2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISO& serves as a ligand in catalysts that promote the cyclization of alkenes with alcohols or amines, leading to the formation of cyclic products.
Used in Catalyst for Cascade cyclization of diynes:
2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISO& is utilized as a ligand in catalysts for cascade cyclization of diynes, enabling the formation of complex cyclic structures through a series of reactions in a single operation.
Used in Catalyst for Hydroarylation of allenes:
This ligand is employed in catalysts for the hydroarylation of allenes, a reaction that involves the highly regioselective formation of carbon-carbon bonds, producing six-membered rings with high selectivity and efficiency.
Used in Catalyst for Alkyne cyclizations:
In alkyne cyclizations, 2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISO& acts as a ligand in catalysts that promote the cyclization of alkynes, leading to the formation of cyclic products with high selectivity.
Used in Catalyst for Holey catalytic environment:
2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISO& is used as a ligand in catalysts designed for reactions in a "Holey" catalytic environment, where its steric and electronic properties contribute to the efficiency and selectivity of the catalytic process.

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

A Gold Carbene Manifold to Prepare Fused γ-Lactams by Oxidative Cyclisation of Ynamides

Gold-catalysed oxidative cyclisation reactions of ynamides offer great promise in γ-lactam synthesis but are limited by preferential over-oxidation to form α-keto imides. Evaluating the factors that might limit N-cyclisation pathways led to effective gold-catalysed conditions that allow access to different fused γ-lactams on changing the ynamide N-substituent and accommodate previously incompatible substitution patterns. New and efficient methods for the synthesis of functionalised 3-aryl indoles and cyclohepta[c]pyrrol-1-one derivatives are presented. These conditions illustrate the complementarity of gold catalysis to other metals.

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.

Alkyne Difunctionalization by Dual Gold/Photoredox Catalysis

Highly selective tandem nucleophilic addition/cross-coupling reactions of alkynes have been developed using visible-light-promoted dual gold/photoredox catalysis. The simultaneous oxidation of AuI and coordination of the coupling partner by photo-generated aryl radicals, and the use of catalytically inactive gold precatalysts allows for high levels of selectivity for the cross-coupled products without competing hydrofunctionalization or homocoupling. As demonstrated in representative arylative Meyer-Schuster and hydration reactions, this work expands the scope of dual gold/photoredox catalysis to the largest class of substrates for gold catalysts and benefits from the mild and environmentally attractive nature of visible-light activation. United we stand! Tandem nucleophilic addition/cross-coupling reactions have been developed with challenging alkynes using a visible-light-promoted dual gold/photoredox catalytic system (see scheme). High levels of selectivity for the cross-coupled products were obtained without competition from the homocoupling or conventional hydrofunctionalization.

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.

Gold catalysis: Biarylphosphine ligands as key for the synthesis of dihydroisocoumarins

Agold-catalyzed phenol synthesis was successfully used in the synthesis of dihydroisocoumarins for the first time.Alarge number of gold(I) complexes were prepared and tested; only complexes based on the biarylphosphine motif were successful. CSIRO 2014.

Dialkylbiarylphosphine complexes of gold(I) halides. Gold-aryl π-interactions in the solid state

Dialkylbiarylphosphines are an emerging ligand set that promote catalytic reactions of electrophilic late transition-element centers through dative interactions of the biaryl arm with the metal site. Presented here are syntheses and crystal structures of