94569-94-5

Upstream product

• 591-50-4 iodobenzene 
• 1807-68-7 diazodimedone 
• 35024-12-5 (4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine 
• 126-81-8 dimedone 
• 100-42-5 styrene 
• 140-88-5 ethyl acrylate 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 104-88-1 4-chlorobenzaldehyde 
• 75-15-0 carbon disulfide 

Downstream Products

• 72035-56-4 5,5-dimethyl-3-phenoxycyclohex-2-en-1-one 

Relevant academic research and scientific papers

Construction of Diverse Dihydrodibenzofuranones by Migration/Intramolecular Arylation of Iodonium Ylides

A novel and facile methodology for synthesizing diverse dihydrodibenzofuranones from easily accessible cyclic iodonium ylides is achieved. This protocol proceeds through the aryl migration of iodonium ylide followed by Pd-catalyzed intramolecular arylatio

Support-Free Pd3Co NCs as an Efficient Heterogeneous Nanocatalyst for New Organic Transformations of C?C Coupling Reactions

A support-free heterogeneous Pd3Co nanostructured composite (NC), synthesized through a hydrothermal route, acted as an effective catalytic system in multivariate Heck-, Sonogashira-, and Suzuki-type coupling reactions of iodonium ylides. The XPS analysis of the bimetallic Pd3Co NCs confirmed the elemental composition as 75 % palladium and 25 % cobalt. Furthermore, high-resolution (HR) TEM analysis confirmed the spherical morphology of the Pd3Co bimetallic nanoparticles. The average diameter of the NCs is 14.8 nm. The coupling reaction proceeded through the generation of α-iodoenones with simultaneous migration of the phenyl group, thereby giving a scaffold with higher atom economy. The heterogeneous Pd3Co NCs were recycled and reused without any significant change in catalytic ability for up to five reaction cycles. The high concentration of Pd and association of cobalt into the lattice of palladium appears to enhance its catalytic ability for the diverse coupling reactions in comparison with its monometallic counterparts as well as with bimetallic NCs with a comparatively lesser amount of Pd.

Mono- and binuclear copper(I) complexes of thionucleotide analogues and their catalytic activity on the synthesis of dihydrofurans

The reaction of copper(I) halides with 2-thiouracil (TUC), 6-methyl-2-thiouacil (MTUC), and 4-methyl-2-mercaptopyrimidine (MPMTH) in the presence of triphenylphosphine (tpp) in a 1:1:2 molar ratio results in a mixed-ligand copper(I) complex with the formulas [Cu2(tpp) 4(TUC)Cl] (1), [Cu2(tpp)4(MTUC)Cl] (2), [Cu(tpp)2(MPMTH)Cl]·1/2CH3OH (3), [Cu(tpp)2(MTUC)Br] (4), and [Cu(tpp)2(MTUC)I] ·1/2CH3CN (5). The complexes have been characterized by FT-IR, 1H NMR, and UV-vis spectroscopic techniques and single-crystal X-ray crystallography. Complexes 1 and 2 are binuclear copper(I) complexes. Two phosphorus atoms from tpp ligands are coordinated to the copper(I) ions, forming two units that are linked to each other by a deprotonated TUC or MTUC chelating ligand through a sulfur bridge. A linear Cu-S-Cu moiety is formed. The tetrahedral geometry around the metal centers is completed by the nitrogen-donor atom from the TUC or MTUC ligand for the one unit, while for the other one, it is completed by the chloride anion. Two phosphorus atoms from two tpp ligands, one sulfur atom from MPMTH or MTUC ligand, and one halide anion (Cl, Br, and I) form a tetrahedron around the copper ion in 3-5 and two polymorphic forms of 4 (4a and 4b). In all of the complexes, either mono- or binuclear intramolecular O-H...X hydrogen bonds enhance the stability of the structures. On the other hand, in almost all cases of mononuclear complexes (with the exception of a symmetry-independent molecule in 4a), intermolecular NH...O hydrogen-bonding interactions lead to dimerization. Complexes 1-5 were studied for their catalytic activity for the intermolecular cycloaddition of iodonium ylides toward dihydrofuran formation by HPLC, 1H NMR, and LC-HRMS spectroscopic techniques. The results show that the geometry and halogen and ligand types have a strong effect on the catalytic properties of the complexes. The highest yield of dihydrofurans was obtained when linear complexes 1 and 2 were used as the catalysts. The activity of the metal complexes on the copper(I)-catalyzed and uncatalyzed intramolecular cycloaddition of iodonium ylide is rationalized through electronic structure calculation methods, and the results are compared with the experimental ones.

A new iodonium ylide-based three-component reaction leading to 2-spirosubstituted dihydrofurans under microwave irradiation

A new iodonium ylide-based three-component reaction for the synthesis of highly functionalized 2-spirosubstituted dihydrofurans starting from readily available common reactants has been developed under microwave irradiation. The procedure is facile, avoid

Synthesis and structural characterization of new cu(I) complexes with the antithyroid drug 6-n-propyl-thiouracil. Study of the cu(I)-catalyzed intermolecular cycloaddition of iodonium ylides toward benzo[b]furans with pharmaceutical implementations

The reaction of copper(I) iodide with 6-n-propylthiouracil (ptu) in the presence or absence of the triphenylphosphine (tpp) or tri(p-tolyl)phosphine (tptp) in a 1:1:2 molar ratio forms the mixed ligand Cu(I) complex with formula [CuI(ptu)2](tol

New highly soluble dimedone-derived iodonium ylides: Preparation, X-ray structure, and reaction with carbodiimide leading to oxazole derivatives

Highly soluble dimedone-derived o-alkoxyphenyliodonium ylides have been prepared and characterized by single crystal X-ray diffraction. These new iodonium ylides are useful reagents for the preparation of oxazole derivatives by reaction with carbodiimides. The Royal Society of Chemistry 2012.

Efficient synthesis of β-substituted α-haloenones by rhodium(II)-catalyzed and thermal reactions of iodonium ylides

Rhodium(II)catalyzed and thermal reaction of iodonium ylides are described. Rhodium(II)-catalyzed reactions of iodonium ylides with benzyl halides and acid halides afforded α-chloro-α,β-enones and α-bromo-α,β-enones in good yields, whereas thermal reactions of iodonium ylides in a solvent such as benzene afforded α-iodo-α,β-enones in good yields.

Capture of Electron-Deficient Species with Aryl Halides. New Syntheses of Hypervalent Iodonium Ylides

We have demonstrated the aryl iodide capture of β-diketocarbenes, generated from the diazo compound by using rhodium(II) acetate, under very mild conditions.This is a useful general preparative method for iodonium ylides under non-hydroxylic conditions.The termal, catalytic, and photochemical decompositions of various azides in the presence of aryl iodides were carried out.With highly reactive nitrenes, intramolecular rearrangement takes precedence over capture.In the case of p-tuloenesulfonyl azide, thermolysis in the presence of aryl iodides requires conditions under which the iminoiodane is itself decomposed.The capture of oxene by iodobenzene is discussed.The application of these capture processes is discussed as a synthetic route to hypervalent ylides as well as on the basis of mechanism.

1,3-Oxathiole-2-thiones from the Reaction of Carbon Disulfide with Zwitterionic Iodonium Compounds

We have synthesized 1,3-oxathiole-2-thiones from the reaction of zwitterionic iodonium compounds with carbon disulfide.The reaction is shown to be photochemical and possible pathways are discussed.