Reaction Of Aryl Iodides Research Articles

Catalyzed C–C Coupling of Aryl Iodides and Boronic Acids

An efficient La2O3-catalyzed new route for the carbon-carbon bond formation in particular, symmetrical and unsymmetrical biphenyls has been developed, which proceeds through carbon-carbon coupling reaction of aryl iodides with boronic acids. The reaction provided the desired products in moderate-to-good yields with a wide range of functional group tolerance.

ChemInform Abstract: Direct Synthesis of Diaryl Sulfides by Copper‐Catalyzed Coupling of Aryl Halides with Aminothiourea.

AbstractSymmetrical diaryl sulfides are prepared by reaction of aryl iodides with aminothiourea.

Synthesis and application of modified polystyrene-supported palladium nanoparticles as a new heterogeneous catalyst for Heck and Suzuki cross-coupling reactions

A new nitrogen-containing phosphinite ligand based on modified Merrifield resin was synthesized and characterized. This ligand was combined with PdCl2 to afford efficient catalyst for Heck and Suzuki cross-coupling reactions. The catalyst was highly efficient for cross-coupling reactions of aryl iodides, bromides and also chlorides with olefinic compounds. Aryl chlorides are usually inactive in coupling reactions, but with this catalytic system, excellent result was gained in the presence of tetrabutylammonium bromide. Transmission electron microscopy of catalyst shows that palladium was well dispersed and of typical diameter of 8–30 nm. The X-ray powder diffraction pattern of the Pd catalyst was consistent with the metallic Pd (0). Elemental analysis of Pd by ICP-OES and hot filtration test shows low leaching of the metal into solution from the supported catalyst which confirms the full heterogeneous character of the catalytically active species. Short reaction times, excellent yields and recyclability are among the advantages of this polymeric catalytic system. The catalyst can be reused for many times without loss in its efficiency.

ChemInform Abstract: Highly Effective Recyclable Palladium‐Catalyzed Ligand‐Free Heck Reactions under Aerobic Conditions.

AbstractThe reaction of aryl iodides with a variety of reactive olefins is successfully achieved in the presence of Bu4NF.

ChemInform Abstract: An Alternative Approach for the Synthesis of Aryl—Alkyl Tellurides: Reaction of Aryl Iodides with Metal Alkyltellurolates Promoted by CuI.

AbstractThe title reaction tolerates a wide range of functional groups at the aryl iodides.

ChemInform Abstract: Polyacrylonitrile Fiber Mat Supported Palladium Catalyst for Mizoroki—Heck Reaction in Aqueous Solution.

AbstractThe heterogeneous palladium catalyst, prepared by electrospinning, shows excellent activity towards reactions of aryl iodides with various acrylates under microwave irradiation.

Palladium‐Catalyzed Reaction of Aryl Iodides with ortho‐Bromoanilines and Norbornene/Norbornadiene: Unexpected Formation of Dibenzoazepine Derivatives

Palladium‐Catalyzed Reaction of Aryl Iodides with <i>ortho</i>‐Bromoanilines and Norbornene/Norbornadiene: Unexpected Formation of Dibenzoazepine Derivatives

Palladium‐Catalyzed Reaction of Aryl Iodides with ortho‐Bromoanilines and Norbornene/Norbornadiene: Unexpected Formation of Dibenzoazepine Derivatives

Palladium‐Catalyzed Reaction of Aryl Iodides with <i>ortho</i>‐Bromoanilines and Norbornene/Norbornadiene: Unexpected Formation of Dibenzoazepine Derivatives

An alternative approach for the synthesis of aryl–alkyl tellurides: reaction of aryl iodides with metal alkyltellurolates promoted by CuI

Aryl iodides react with metal organotellurolates in tetrahydrofuran/dimethylformamide in the presence of CuI (5 mol %) or CuI (5 mol %) and 1,10-phenanthroline (10 mol %) to afford the corresponding aryl–alkyl tellurides in good yields.

Phosphane‐Free Copper‐Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids with Aryl Halides under Aerobic Conditions

AbstractA phosphane‐free copper‐catalyzed decarboxylative cross‐coupling reaction of alkynyl carboxylic acids with aryl halides was developed. CuBr (1–5 mol‐%) was used as a catalyst in the presence of a β‐diketone ligand in air. The reactions of aryl iodides were conducted in the absence of a Pd catalyst. The ligand plays a key role in this kind of copper catalysis. NaNO2 was disclosed to efficiently improve this kind of decarboxylative cross‐coupling when a nitro group was not present in the substrates.

ChemInform Abstract: A Phosphine‐Free Carbonylative Cross‐Coupling Reaction of Aryl Iodides with Arylboronic Acids Catalyzed by Immobilization of Palladium in MCM‐41.

AbstractThe reaction affords unsymmetrical biaryl ketones (IV) and various electron‐donating and electron‐withdrawing grous on the aryl iodide (II) are tolerated.

ChemInform Abstract: Magnetite (Fe3O4) Nanoparticles‐Catalyzed Sonogashira—Hagihara Reactions in Ethylene Glycol under Ligand‐Free Conditions.

A novel application of nanoparticles of paramagnetic magnetite (Fe 3 O 4 ) as an efficient catalyst for carbon-carbon bond formation via the Sonogashira-Hagihara reaction under heterogeneous ligand-free conditions in ethylene glycol (EG) is described. By using this catalyst, arylalkynes are produced from the reaction of aryl iodides and activated heteroaryl bromides with alkynes. The results are reproducible using the catalyst, which was prepared from different sources. The catalyst is easily separated by an external magnetic field from the reaction mixture. The separated catalyst can be recycled for several consecutive runs without appreciable loss of its catalytic activity.

Magnetite (Fe3O4) Nanoparticles‐Catalyzed Sonogashira– Hagihara Reactions in Ethylene Glycol under Ligand‐Free Conditions

AbstractA novel application of nanoparticles of paramagnetic magnetite (Fe3O4) as an efficient catalyst for carbon‐carbon bond formation via the Sonogashira–Hagihara reaction under heterogeneous ligand‐free conditions in ethylene glycol (EG) is described. By using this catalyst, arylalkynes are produced from the reaction of aryl iodides and activated heteroaryl bromides with alkynes. The results are reproducible using the catalyst, which was prepared from different sources. The catalyst is easily separated by an external magnetic field from the reaction mixture. The separated catalyst can be recycled for several consecutive runs without appreciable loss of its catalytic activity.

ChemInform Abstract: Room‐Temperature Direct Arylation of Polyfluorinated Arenes under Biphasic Conditions.

AbstractUsing an immiscible mixture of ethyl acetate and water, the reaction of aryl iodides with electron‐poor polyfluoroarenes proceeds at room temperature.

ChemInform Abstract: Preparation of Ethyl Arylpropiolates from Aryl Iodides by Palladium- Catalyzed Cross-Coupling Reaction.

The palladium-catalyzed cross-coupling reaction of aryl iodides with 3,3,3-triethoxy-1-propyne gave 1-aryl-3,3,3-triethoxy-1-propynes which were converted to the corresponding ethyl arylpropiolates. The arylpropiolates were also synthesized from the cross-coupling reactions of aryl iodides with 2-ethoxycarbonyl-1-ethynylzinc chloride or ethyl (tributylstannyl)propiolate, but the reactions were not generally applicable

Synthesis ofortho-Teraryls by Sequential Unsymmetrical Aryl Cross-Coupling

Selectively substituted o-teraryls are accessible by a palladium/norbornene-catalyzed reaction of aryl iodides, aryl bromides, and arylboronic acids in an ordered sequence. The reason for the high selectivity is the presence of diethyl maleate coordinated to palladium as a ligand.

ChemInform Abstract: A Highly Efficient, Ligand‐Free, and Recyclable Cu2S‐Catalyzed Coupling of Aryl Iodides with Diaryl Disulfides.

AbstractThe reaction proceeds best using Fe as a reductant in DMSO.

ChemInform Abstract: Copper-Promoted Reaction of Aryl Iodides with Activated Methine Compounds.

The reaction of aryl iodides with an activated methine compound, diethyl acetamidomalonate, can efficiently proceed in the presence of CuI and NaH in DMSO to give diethyl acetamido(aryl)malonates, which may be useful precursors for α-arylglycines, in good yields. Although the reaction with another methine substrate, ethyl 2-cyanopropionate, also affords the expected coupling products, no substitution products are obtained in the case of diethyl methylmalonate, arenes together with an oxidative coupling compound of the ester being formed.

Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol

Oxidative chlorination with HCl/H2O2 in 1,1,1-trifluoroethanol was used to transform aryl iodides into aryliodine(III) dihalides. In this instance 1,1,1‑trifluoroethanol is not only the reaction medium, but is also an activator of hydrogen peroxide for the oxidation of hydrochloric acid to molecular chlorine. Aryliodine(III) dichlorides were formed in 72–91% isolated yields in the reaction of aryl iodides with 30% aqueous hydrogen peroxide and hydrochloric acid at ambient temperature. A study of the effect that substituents on the aromatic ring have on the formation and stability of aryliodine(III) dichlorides shows that the transformation is easier to achieve in the presence of the electron-donating groups (i.e. methoxy), but in this case the products rapidly decompose under the reported reaction conditions to form chlorinated arenes. The results suggest that oxidation of hydrogen chloride with hydrogen peroxide is the initial reaction step, while direct oxidation of aryl iodide with hydrogen peroxide is less likely to occur.

Facile Synthesis of a Family of H8BINOL-Amine Compounds and Catalytic Asymmetric Arylzinc Addition to Aldehydes

A family of optically active H(8)BINOL-AM compounds containing 3,3'-bis-tertiary amine substituents are synthesized by using a one-step reaction of H(8)BINOL with amino methanols that were in situ generated from various cyclic or acyclic secondary amines and paraformaldehyde. The H(8)BINOL-AM compounds are used to catalyze the reaction of functional arylzincs, in situ prepared from the reaction of aryliodides with ZnEt(2), with aldehydes to produce chiral diaryl carbinols and a few arylalkyl carbinols. Through this study, highly enantioselective catalysts were identified. It was found that the H(8)BINOL-AM compounds with sterically less congested cyclic or acyclic amino methyl substituents were more enantioselective than those with more bulky substituents. The pyrrolidinyl derivative (S)-12 in most cases showed greater enantioselectivity than other H(8)BINOL-AM compounds, especially for the challenging ortho-substituted aromatic aldehydes. A H(8)BINOL-AM with 3,3'-bis-sec-amine substituents, prepared by a multistep method, was also used to catalyze the arylzinc addition to aldehydes, but it showed enantioselectivity lower than that of the compounds with tertiary amine groups. It was found for the first time that an aryl bromide, 2-bromothiophene, could be used to prepare an arylzinc reagent by reaction with ZnEt(2). The addition of this heteroarylzinc reagent to an aldehyde in the presence of (S)-12 proceeded with good enantioselectivity.