17851-50-2

Upstream product

• 30698-18-1 bromure de benzoyloxy-3 propyltriphenylphosphonium 
• 1191-99-7 2,3-dihydro-2H-furan 
• 17763-67-6 Phenyl triflate 
• 866641-66-9 Echavarren's catalyst 
• 10229-11-5 4-phenyl-but-3-yn-1-ol 
• 1137-96-8 N-(benzylidene)aniline N-oxide 
• 98-80-6 phenylboronic acid 
• 693-02-7 hex-1-yne 
• 1426437-78-6 C₅H₁₂AuNP⁽¹⁺⁾*F₆Sb^(1-) 
• 591-50-4 iodobenzene 
• 65-85-0 benzoic acid 
• 532-32-1 sodium benzoate 
• 77772-24-8 α-(diphenylmethylsilyl)-γ-butyrolactone 
• 79172-43-3 1-benzoylcyclopropanecarboxylic acid 

Downstream Products

• 2051-95-8 succinylbenzene 

Relevant academic research and scientific papers

Intermolecular Homopropargyl Alcohol Addition to Alkyne and a Sequential 1,6-Enyne Cycloisomerization with Triazole-Gold Catalyst

While gold-catalyzed homopropargyl alcohol cyclization is a known process, a triazole-gold catalyst prevented the intramolecular cyclization in the presence of terminal alkynes. As a result, an intermolecular addition to an alkyne was achieved. A sequential 1,6-enyne cycloisomerization gave the unusual 2,3-dihydrooxepine, which revealed another new reaction path. Diels-Alder reaction of oxepine followed by a 1,3-alkoxyl shift gave hydrobezofuran derivatives in high yields. Diasterioselective reaction of homopropargyl alcohol to final product enabled one-step formation of five stereogenic centers with excellent enantiomeric selectivity.

Enantioselective Oxidative Cyclization/Mannich Addition Enabled by Gold(I)/Chiral Phosphoric Acid Cooperative Catalysis

An enantioselective Mannich-type reaction of 3-butynol and nitrones is described, which affords dihydrofuran-3-ones in good yields and with excellent enantioselectivities. The reaction is initiated by gold-catalyzed alkyne oxidation and modification of the resulting gold carbene species with a tethered hydroxy group to form enolate species; the reaction terminates with an enantioselective Mannich-type addition with the assistance of chiral phosphoric acid (CPA) and hydrogen bonding. This novel pattern of alkyne transformation involving chemical bond cleavage, and a fragment modification and reassembly process, provides an atom- and step-economic method, and is the first example of cooperative asymmetric catalysis in gold-catalyzed alkyne oxidations via an α-oxo gold carbene route.

Palladium complexes with chiral imidazole ligands as potential catalysts for asymmetric C[sbnd]C coupling reactions

Two palladium complexes of the type [Pd(im)2Cl2] containing chiral imidazole ligands (im?=?1-bornyloxymethylene imidazole, 1-fenchyloxymethylyne imidazole) were synthesized and structurally characterized. The square planar structure of one of the complexes was confirmed by the X-ray analysis. The new palladium complexes were tested as catalysts in various C[sbnd]C bond forming reactions, namely Suzuki–Miyaura, carbonylative Suzuki–Miyaura, asymmetric Heck-type coupling reactions and asymmetric conjugate addition of phenylboronic acid to heterocyclic acceptors. In all the reactions the cross-coupling products were obtained with high yield and selectivity under mild conditions. In case of coupling of 2,3-dihydrofuran with phenylboronic acid ee value ca. 10 was observed.

Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction

A novel class of chiral phosphanyl-oxazoline (PHOX) ligands with a conformationally rigid cyclopropyl backbone was synthesized and tested in the intermolecular asymmetric Heck reaction. Mechanistic modelling and crystallographic studies were used to predict the optimal ligand structure and helped to design a very efficient and highly selective catalytic system. Employment of the optimized ligands in the asymmetric arylation of cyclic olefins allowed for achieving high enantioselectivities and significantly suppressing product isomerization. Factors affecting the selectivity and the rate of the isomerization were identified. It was shown that the nature of this isomerization is different from that demonstrated previously using chiral diphosphine ligands.

Palladium catalyzed heck arylation of 2,3-Dihydrofuran-effect of the palladium precursor

Heck arylation of 2,3-dihydrofuran with iodobenzene was carried out in systems consisting of different palladium precursors (Pd2(dba) 3, Pd(acac)2, PdCl2(cod), [PdCl(allyl)] 2, PdCl2(PhCN)

Quantitative evaluation of the stability of gem -diaurated species in reactions with nucleophiles

The reactivity of diaurated species toward nucleophiles was investigated. The reaction yields vinyl gold species and is described as simple SN2 ligand exchange at gold. Using suitably strong nucleophiles, equilibrium constants were determined to measure the stability of various diaurated species. On the basis of these equilibrium constants the influence of ligand and the nature of vinyl cores on the stability were analyzed. These results have direct implication for gold catalysis: it was demonstrated that vinyl gold intermediates bind the catalytic LAu+ species generally stronger than an alkyne (the substrate) by a factor of 106-109. This demonstrates that the formation of diaurated species from vinyl gold intermediates is thermodynamically favored in a catalytic reaction.

Synthesis of gem-diaurated species from alkynols

A number of enol ether-derived diaurated species were synthesized directly from different alkynols and cationic gold complexes in the presence of a non-nucleophilic base (proton sponge). The reaction can be easily applied for in situ generation of diaurated species from all common types of hydroalkoxylation substrates: 5-endo, 5-exo/6-endo, 6-exo/7-endo and intermolecular types. Six examples were also synthesized in individual state as stable hexafluoroantimonate salts. Whereas diaurated species are obtained reliably from all conventional mononuclear gold catalysts, application of binuclear ones often gave diaurated species with unusual properties. The preliminary results point to complexities of behavior of binuclear gold catalysts and would require more research in future for this subclass. The formation of diaurated species from various gold-oxo compounds (LAu)2OH+, (LAu) 3O+, and LAuOH (L=phosphine ligand) was also studied. Of these three types, only (LAu)2OH+ is reactive, whereas (LAu)3O+ and LAuOH are not reactive alone but require acidic promoters to enable the reaction. These differences in reactivity were explained by ability of these compounds to generate the necessary acetylene π-complex intermediate. Catch the gold fish: A number of enol ether derived diaurated species were synthesized directly from different alkynols and cationic gold complexes in the presence of a non-nucleophilic base (proton sponge; see scheme). The reaction can be easily applied for the in situ generation of diaurated species from all common types of hydroalkoxylation substrates: 5-endo, 5-exo/6-endo, 6-exo/7-endo and even intermolecular types. The reactivity of various gold oxo compounds (LAu)2OH+, (LAu) 3O+, and LAuOH (L=phosphine ligand) towards alkynols was also examined. Copyright

Effect of chiral ionic liquids on palladium-catalyzed Heck arylation of 2,3-dihydrofuran

It is demonstrated that a relatively small amount of IL (IL = ionic liquid) can dramatically affect conversion in the Heck arylation of 2,3-dihydrofuran with iodobenzene, catalyzed by Pd(OAc)2 in DMF as a solvent. In all reactions, 2-phenyl-2,3

Synthesis of bisquinolone-based mono- and diphosphine ligands of the aza-BINAP type

(Chemical Equation Presented) Mono- and bisphosphine ligands based on the 4,4′-bisquinolone structural framework (BIQUIP ligands) were generated by direct microwave-assisted palladium-catalyzed carbon-phosphorus cross-coupling reactions employing the corr

Exploiting noninnocent (E,E)-dibenzylideneacetone (dba) effects in palladium(0)-mediated cross-coupling reactions: Modulation of the electronic properties of dba affects catalyst activity and stability in ligand and ligand-free reaction systems

The reactivity of palladium(0) complexes, [Pd2 0(dba-n,n′-Z)3] (n,n′-Z = 4,4′-F; 4,4′-CF3; 4,4′-H; 4,4′-MeO) and [Pd 0(dba-n,n′-Z)2] (n,n′-Z = 4,4′-CF 3; 4,4′-H; 3,3′,5,5′-OMe),