Coupling Of Aryl Iodides Research Articles

ChemInform Abstract: Efficient Copper Catalyzed C—N Coupling Reaction in Water by Using 2‐Hydroxybenzohydrazides as Ligands.

Abstract2‐Hydroxybenzohydrazides are efficiently applied as ligands in the copper‐catalyzed coupling of aryl iodides and bromides with a variety of N‐heterocycles as well as aniline and benzylamine (X).

ChemInform Abstract: Copper‐Free Sonogashira Coupling Reaction Catalyzed by PVC‐Supported Triazine Palladium(II) Complex under Aerobic Conditions.

AbstractA polyvinyl chloride supported triazine Pd(II)‐complex is developed and efficiently applied as heterogeneous recyclable catalyst for the Sonogashira coupling of aryl iodides and bromides.

ChemInform Abstract: Ligand‐Free Pd/Cu‐Catalyzed Decarboxylative Coupling of Aryl Iodides with α‐Oxocarboxylates.

AbstractAn attractive alternative to traditional cross‐coupling approaches for aryl ketone synthesis with wide functional group tolerance is developed.

A Simple and Efficient Palladium Catalyst of Nitrogen-Based Ligand for Cu(I)- and Amine-Free Sonogashira Reaction

Glycine, as a kind of commercially available and inexpensive ligand, is used to prepare an air-stable and water-soluble catalyst used in Sonogashira reaction in our study. In the presence of 1% [PdCl2(NH2CH2COOH)2] as catalyst, excellent catalytic activity towards the Sonogashira coupling of aryl iodides with terminal alkynes without using any additive such as Cu(I)-cocatalyst is observed in a mixture of water and acetone (3/3 mL) under air at 60 °C with NaOH as a base, giving products in good to excellent yields.

A theoretical investigation on palladium-catalyzed one-pot coupling of aryl iodides, alkynes, and amines through CN bond cleavage for the synthesis of indole derivatives

Detailed mechanism of one-pot coupling of aryl iodides, alkynes, and amines catalyzed by a palladium complexes is studied using density functional theory. The reaction of three-component proceeds in four steps after the insertion of alkyne into CI bond. The four-component case comprises eight steps incorporating two times of nucleophilic addition. The CN bond cleavage is rate-limiting. The reaction sequence is maintained the same. The function of metal Pd is reflected by the coordination ability and electrophility of different oxidation state. The high selectivity of ligand is originated from the style of electron distribution in CN bond cleavage and amination steps. We also discuss the amination from a bonding orbital matching perspective by means of frontier molecular orbital analysis. © 2014 Wiley Periodicals, Inc.

ChemInform Abstract: A Highly Active and Easily Recoverable Chitosan@Copper Catalyst for the C—S Coupling and Its Application in the Synthesis of Zolimidine.

AbstractThe newly prepared chitosan/Cu system catalyzes the coupling of aryl iodides (I) with sodium sulfinates (II) to give sulfones (III) (25 examples) in good to excellent yields.

Reductive Coupling of Aryl Iodides with CF3CH2I in the Presence of Copper

Reductive Coupling of Aryl Iodides with CF3CH2I in the Presence of Copper

Ligand‐free Pd/Cu‐catalyzed decarboxylative coupling of aryl iodides with α‐oxocarboxylates

This paper describes a palladium/copper‐catalyzed decarboxylative coupling of aryl iodides with α‐oxocarboxylates. The cross‐coupling reaction gives high chemical yields of aryl ketones and has wide functional group tolerance, making the transformation an attractive alternative to the traditional cross‐coupling approaches for aryl ketones. Copyright © 2014 John Wiley & Sons, Ltd.

“Click” Dendrimer‐Stabilized Palladium Nanoparticles as a Green Catalyst Down to Parts per Million for Efficient CC Cross‐Coupling Reactions and Reduction of 4‐Nitrophenol

AbstractThe concept of the nanoreactor valuably contributes to catalytic applications of supramolecular chemistry. Therewith molecular engineering may lead to organic transformations that minimize the amount of metal catalyst to reach the efficiency of enzymatic catalysis. The design of the dendritic nanoreactor proposed here involves hydrophilic triethylene glycol (TEG) termini for solubilization in water and water/ethanol mixed solvents combined with a hydrophobic dendritic interior containing 1,2,3‐triazole ligands that provide smooth stabilization of very small (1 to 2 nm) palladium nanoparticles (PdNPs). The PdNPs stabilized in such nanoreactors are extraordinarily active in water/ethanol (1/1) for the catalysis of various carbon‐carbon coupling reactions (Suzuki–Miyaura, Heck and Sonogashira) of aryl halides down to sub‐ppm levels for the Suzuki–Miyaura coupling of aryl iodides and aryl bromides. The reduction of 4‐nitrophenol to 4‐aminophenol in water also gives very impressive results. The difference of reactivity between the two distinct dendrimers with, respectively, 27 (G0) and 81 (G1) TEG termini is assigned to the difference of PdNP core size, the smaller G0 PdNP core being more reactive than the G1 PdNP core (1.4 vs. 2.7 nm), which is also in agreement with the leaching mechanism.magnified image

Copper-promoted reductive coupling of aryl iodides with 1,1,1-trifluoro-2-iodoethane.

An efficient Cu-promoted reductive coupling of aryl iodides with 1,1,1-trifluoro-2-iodoethane has been developed. This reaction could occur in good yields under milder conditions as compared with previous studies. The reaction tolerated nitro, formyl, ester, ether, carbonyl, sulfonyl, and even azo groups.

Palladium‐Catalyzed One‐Pot Three‐ or Four‐Component Coupling of Aryl Iodides, Alkynes, and Amines through CN Bond Cleavage: Efficient Synthesis of Indole Derivatives

An efficient synthesis of N-substituted indole derivatives was realized by combining the Pd-catalyzed one-pot multicomponent coupling approach with cleavage of the C(sp(3))-N bonds. Three or four components of aryl iodides, alkynes, and amines were involved in this coupling process. The cyclopentadiene-phosphine ligand showed high efficiency. A variety of aryl iodides, including cyclic and acyclic tertiary amino aryl iodides, and substituted 1-bromo-2-iodobenzene derivatives could be used. Both symmetric and unsymmetric alkynes substituted with alkyl, aryl, or trimethylsilyl groups could be applied. Cyclic secondary amines such as piperidine, morpholine, 4-methylpiperidine, 1-methylpiperazine, 2-methylpiperidine, and acyclic amines including secondary and primary amines all showed good reactivity. Further application of the resulting indole derivatives was demonstrated by the synthesis of benzosilolo[2,3-b]indole.

Water-dispersible and magnetically separable gold nanoparticles supported on a magnetite/s-graphene nanocomposite and their catalytic application in the Ullmann coupling of aryl iodides in aqueous media

The water-dispersible and magnetic separable Au/Fe3O4/s-G nanocomposite was used as an effective and reusable heterogeneous catalyst for the Ullmann homocoupling.

Copper-catalyzed carbonylative Suzuki coupling of aryl iodides with arylboronic acids under ambient pressure of carbon monoxide

An efficient and ligandless nanocopper-catalyzed carbonylative cross-coupling of aryl iodides with arylboronic acids at ambient CO pressure in poly(ethylene glycol), has been developed.

ChemInform Abstract: Ferrocene‐Tagged N‐Heterocyclic Carbene‐Pd Complex for Suzuki—Miyaura Coupling.

We demonstrate that the ferrocene-tagged N-heterocyclic carbene (NHC)-Pd(II) complex can act as an efficient heterogeneous catalyst for Suzuki–Miyaura cross-coupling in dimethylformamide (DMF)-water. This complex was found to be an active and efficient catalyst for coupling of aryl iodides, bromides, and even less reactive chlorides with boronic acids and pinacol ester of boronic acid.

Silica‐supported terpyridine palladium(II) complex as an efficient and reusable catalyst for Heck and Suzuki cross‐coupling reactions

Silica‐supported terpyridine palladium(II) was prepared and used as an effective and recyclable catalyst in Mizoroki–Heck and Suzuki–Miyaura coupling reactions. The catalyst was very effective for the Mizoroki–Heck reaction of aryl halides with olefins and conversion was in most cases excellent. The catalyst showed good thermal stability (up to 230 °C) and could be recovered and reused for four reaction cycles. The Suzuki coupling of aryl iodides with aryl boronic acids in the presence of the catalyst was also investigated and the reaction proceeded with a short reaction time and excellent conversion. Copyright © 2013 John Wiley & Sons, Ltd.

ChemInform Abstract: The Pd(0) Nanoparticles Stabilized by Collagen Fibres as a Recyclable Heterogeneous Catalyst for the Stille Reaction under Aerobic Condition.

AbstractA new protocol for the Stille coupling of aryl iodides with organostannanes under aerobic conditions using a collagen fibre‐supported Pd nanoparticle catalyst is developed.The catalyst can be easily recovered by filtration and reused multiple times without significant loss of activity.

ChemInform Abstract: Pd Immobilized in Mesoporous Silica Particles as Recyclable Catalysts for Suzuki—Miyaura Coupling: Cooperative Effects Exerted by Co‐Immobilized Amine Functionalities.

AbstractA monofunctionalized mesoporous silica immobilized Pd‐catalyst is demonstrated to efficiently catalyze the Suzuki coupling of aryl iodides and bromobenzene, but not of chlorobenzene.

Cryptand-22 as an Efficient Ligand for the Palladium-Catalyzed Mizoroki–Heck Reaction under Air

An efficient catalytic system for the Mizoroki–Heck cross-coupling reaction was developed based on the air- and heat-stable palladium(II) chloride–cryptand 22 complex. The complex is a highly active catalyst for coupling of aryl iodides, bromides, or chlorides with various olefins.

Copper-catalyzed coupling of aryl iodides and tert-butyl β-keto esters: efficient access to α-aryl ketones and α-arylacetic acid tert-butyl esters

CuI/trans-4-hydroxy-l-proline catalyzed coupling of aryl iodides with tert-butyl β-keto esters proceeded smoothly at 40 °C in DMF, providing α-aryl ketones after acid-promoted deprotection and decarboxylation of tert-butyl ester group. While CuI/2-picolinic acid catalyzed coupling of aryl iodides with tert-butyl acetoacetate at 70 °C in dioxane delivered α-arylacetic acid tert-butyl esters upon spontaneous deacylation. A wide range of functional groups, such as acetyl, methoxy, nitrile, nitro, bromo, and chloro were compatible with the reaction conditions.

Ferrocene-tagged N-heterocyclic carbene-Pd complex for Suzuki–Miyaura coupling

We demonstrate that the ferrocene-tagged N- heterocyclic carbene (NHC)-Pd(II) complex can act as an efficient heterogeneous catalyst for Suzuki-Miyaura cross- coupling in dimethylformamide (DMF)-water. This com- plex was found to be an active and efficient catalyst for coupling of aryl iodides, bromides, and even less reactive chlorides with boronic acids and pinacol ester of boronic acid.