84224-89-5

Upstream product

• 20050-22-0 2t-bromo-1.2c-diphenyl-1r-(4-chloro-phenyl)-ethylene 
• 100-42-5 styrene 
• 591-50-4 iodobenzene 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 637-87-6 1-Chloro-4-iodobenzene 
• 108-86-1 bromobenzene 
• 5172-02-1 1-chloro-4-(2-phenylethynyl)benzene 
• 143-66-8 sodium tetraphenyl borate 
• 873-73-4 4-n-chlorophenylacetylene 
• 106-39-8 bromochlorobenzene 
• 501-65-5 diphenyl acetylene 
• 1679-18-1 4-Chlorophenylboronic acid 
• 84224-92-0 1-(4-chlorophenyl)-1,2-diphenylethanol 
• 108-90-7 chlorobenzene 

Downstream Products

• 20050-23-1 (Z)-1-bromo-2-(4-chloro-phenyl)-1,2-diphenyl-ethene 

Relevant academic research and scientific papers

One-pot Sonogashira–Hydroarylation reaction catalyzed by anionic palladium complexes in an aqueous medium

It was found that anionic Pd(II) complexes of type [CA]2[PdCl4] and [CA]2[Pd2Cl6] (CA = imidazolium or pyridinium cation) are effective catalysts for copper-free Sonogashira coupling in an aqueous med

Nickel-Catalyzed Hydroarylation of Alkynes under Reductive Conditions with Aryl Bromides and Water

An operationally simple nickel-catalyzed hydroarylation reaction for alkynes is described. This three-component coupling reaction utilizes commercially available alkynes and aryl bromides, along with water and Zn. An air-stable and easily synthesized Ni(II) precatalyst is the only entity used in the reaction that is not commercially available. This reductive cross-coupling reaction displays a fairly unusual anti selectivity when aryl bromides with ortho substituents are used. In addition to optimization data and a preliminary substrate scope, complementary experiments including deuterium labeling studies are used to provide a tentative catalytic mechanism. We believe this report should inspire and inform other Ni-catalyzed carbofunctionalization reactions.

Controlled mono- and double-Heck reaction catalyzed by a dicarbene dipalladium complex

The phosphine-free mono- and double-Heck reaction of terminal olefins with electron-deficient and electron-rich aryl halides (iodides and bromides) is described. These reactions are catalyzed by the dicarbene dipalladium complex 1 by controlling the stoichiometry of the aryl halide and the olefine, the loading of the palladium catalyst, as well as using different base, and with or without additive. The procedure of double-Heck reaction allows β,β- diarylation and β,β′-diarylation of terminal olefins and affords trisubstituted olefins in good to excellent yields.

Palladium-catalyzed double arylations of terminal olefins in acetic acid

A palladium-catalyzed Heck diarylation of terminal olefins under ligand-free conditions in acetic acid is described. This procedure allows double arylation of terminal olefins affording trisubstituted olefins in good to excellent yields. The methodology is applicable to the coupling of both electron-deficient and electron-rich aryl iodides leading to symmetrical and unsymmetrical β,β-diarylated alkenes.

A simple, multidimensional approach to high-throughput discovery of catalytic reactions

Transition metal complexes catalyze many important reactions that are employed in medicine, materials science, and energy production. Although high-throughput methods for the discovery of catalysts that would mirror related approaches for the discovery of medicinally active compounds have been the focus of much attention, these methods have not been sufficiently general or accessible to typical synthetic laboratories to be adopted widely. We report a method to evaluate a broad range of catalysts for potential coupling reactions with the use of simple laboratory equipment. Specifically, we screen an array of catalysts and ligands with a diverse mixture of substrates and then use mass spectrometry to identify reaction products that, by design, exceed the mass of any single substrate. With this method, we discovered a copper-catalyzed alkyne hydroamination and two nickel-catalyzed hydroarylation reactions, each of which displays excellent functional-group tolerance.

Metal triflate-catalyzed regio- And stereoselective friedelCrafts alkenylation of arenes with alkynes in an ionic liquid: Scope and mechanism

In the metal triflate-catalyzed hydroarylation of alkynes, employing an ionic liquid dramatically enhanced the catalytic activities, resulting in broadening the scope of substrates (arenes and alkynes). In some cases, even reactions that were not possible in conventional organic solvents proceeded smoothly in ionic liquids. Moreover, the ionic liquid phase containing catalyst could be readily recovered by simple decantation of the organic layer after reaction and reused for the following runs without any significant loss of activity. Mechanistic studies including 13C NMR analysis of reaction intermediates and isotope experiments confirmed for the first time that this type of reaction proceeds via vinyl cationic intermediates.

Sequential reactions of trimethylstannyl anions with vinyl chlorides and dichlorides by the SRN1 mechanism followed by palladium-catalyzed cross-coupling processes

The reactions of trimethylstannyl ions (Me3Sn-) with vinyl chlorides in liquid ammonia give good yields of vinylstannanes. Some of them react in the dark, and others need light stimulation to react. The fact that these reactions are inhibited by radical and radical anion traps shows that they occur by the SRN1 mechanism. When the reaction takes place with 1,1-dichloro-1-alkenes, monosubstitution reduced products are formed in an E/Z mixture. The efficient synthesis of triarylolefins by Pd(0)-catalyzed cross-coupling reactions of vinylstannanes with several iodoarenes is reported. Similar yields were obtained in one-pot-type reactions.