13392-79-5

Upstream product

• 917-64-6 methyl magnesium iodide 
• 10547-60-1 4-chloro-4'-methoxybenzophenone 
• 99-91-2 para-chloroacetophenone 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 1073-67-2 4-vinylbenzyl chloride 
• 696-62-8 para-iodoanisole 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 14429-17-5 N-(α-methyl-4-methoxybenzylidene)benzylamine 
• 1190084-46-8 3-(4-methoxyphenyl)-3-methyl-3H-diazirine 
• 1679-18-1 4-Chlorophenylboronic acid 
• 637-87-6 1-Chloro-4-iodobenzene 
• 32117-52-5 1-(1-(4-methoxyphenyl)ethylidene)-2-tosylhydrazine 
• 1421692-99-0 (E)-N'-(1-(4-chlorophenyl)ethylidene)-4-methylbenzenesulfonohydrazide 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 90986-71-3 4-(1-(4-methoxyphenyl)vinyl)-1,1'-biphenyl 
• 86766-88-3 C₁₅H₁₄ClO⁽¹⁺⁾ 
• 10547-60-1 4-chloro-4'-methoxybenzophenone 
• 150716-96-4 3,6-Bis-(4-chloro-phenyl)-3,6-bis-(4-methoxy-phenyl)-[1,2]dioxane 
• 74925-09-0 C₁₅H₁₃ClF₂O 

Relevant academic research and scientific papers

Synthesis of methylated resveratrol and analogues by Heck reactions in organic and aqueous solvents

The Heck reaction under phosphane free conditions using oxime-derived palladacycles or Pd(OAc)2 as catalysts is a general methodology for the synthesis of methoxylated (E)-stilbene derivatives. Couplings can be performed either with (dicyclohexyl)methylamine as base and TBAB in aqueous DMA or in neat water and with Et3N as base in DMA in air and under thermal and microwave conditions. The arylation of different styrenes are performed with 3,5-dimethoxyiodobenzene to afford a series of important biologically active (E)-stilbene derivatives containing the 3,5-dimethoxyphenyl moiety, including resveratrol, piceatannol and pinosilvine, which are efficiently prepared with high regioselectivity and total stereoselectivity (TON up to 104).

Synthesis and characterization of a new zwitterionic palladium complex as an environmentally friendly catalyst for the Heck-Mizoroki coupling reaction in GVL

A new zwitterionic Palladium (II) complex has been synthesized by the one-pot mixing of Pd(OAc)2, 2-aminophenol and (3-formyl-4-hydroxy-5-methylbenzyl) triphenylphosphonium chloride, in refluxing ethanol. The metal complex formed was characterized by 1H NMR, 13C NMR, 31P NMR and X-ray crystallographic technique and its efficiency tested as a homogeneous pre-catalyst in Heck-Mizoroki cross coupling reaction using γ-Valerolactone (GVL) as a biomass-derived green medium. All the products were obtained in good to excellent yields.

A tailored polymeric cationic tag-anionic Pd(ii) complex as a catalyst for the low-leaching Heck-Mizoroki coupling in flow and in biomass-derived GVL

The [PdCl4]2- palladium complex has been immobilized on a polystyrene-type resin loaded with pincer-type imidazolium ionic tag binding sites. The catalytic system (Pd(ii)-POLI-TAG) has proved to be highly active in the definition of an efficient protocol for the Heck-Mizoroki coupling reaction under batch and flow conditions. Importantly, it is shown to be highly robust in combination with a safe non-toxic reaction medium, i.e. biomass-derived GVL, since it could be reused for multiple runs without significantly losing its activity.

Metal-free oxidative cross-coupling of diazirines with arylboronic acids

We report herein a metal-free cross-coupling of diazirines with arylboronic acids under oxidative conditions. The reaction affords a series of substituted olefins. It is proposed that the interaction between the nitrogen on diazirine with arylboronic acid plays a key role in this transformation.

Palladium-Catalyzed One-Pot Reaction of Hydrazones, Dihaloarenes, and Organoboron Reagents: Synthesis and Cytotoxic Activity of 1,1-Diarylethylene Derivatives

A new three-component assembly reaction between N-tosylhydrazones, dihalogenated arenes, and boronic acids or boronate esters was developed, producing highly substituted 1,1-diarylethylenes in good yields. The two C-C bonds formed through this coupling ha

Pd-catalyzed oxidative cross-coupling of N-tosylhydrazones with arylboronic acids

The Pd-catalyzed reaction of N-tosylhydrazones and arylboronic acids provides olefin derivatives. This oxidative cross-coupling is suggested to proceed through a migratory insertion process of a Pd carbene intermediate.

Selective one-pot synthesis of various phenols from diarylethanes

Various substituted phenols were selectively synthesized by a one-pot reaction through the NHPI-catalyzed aerobic oxidation of 1,1-diarylethanes followed by treatment with dilute sulfuric acid. The Royal Society of Chemistry.

Substituent-Dependent Electron-Transfer Induced Photooxygenation of 1,1-Diarylethylenes

Rates and products of 9,10-dicyanoanthracene-sensitized photooxygenations of 1,1-diarylethylenes (1a-r) in acetonitrile were studied.If at least one of the aryl groups carries an electron-donating substituent at the para (or ortho) position (1a-l), 3,3,6,6-tetraaryl-1,2-dioxanes (2a-l) are generated in high yields (85-100percent).Benzophenones (3) are the only other observable products. 1,1-Diphenylethylene (1n) and its m-methoxy (1m), p-chloro (1o,p), and p-nitro (1q,r) derivatives, however, yield mainly benzophenones (3m-r) (>50percent) (the p-nitro compounds only in the presence of biphenyl). 1,2-Dioxanes (2m-p), cyclobutanes (4n-p), and α-tetralones (5m-o) are obtained as side products.Dioxanes, benzophenones, and α-tetralones are products of electron-transfer induced oxygenations involving triplet ground-state molecular oxygen, 3O2.Singlet molecular oxygen, O2(1Δg), contributes to the benzophenone formation from strongly electron-donor substituted diarylethylenes.An exception is the most powerful electron-donor substituted diarylethylene 1a, with which O2(1Δg) undergoes an electron-transfer reaction affording dioxane 2a.Dioxane formation proceeds via free-radical cations 1.+, which enter into a chain reaction with 1, 3O2, and another molecule of 1 to yield dioxane 2 and a new radical cation 1.+ that maintains the chain reaction.The efficiency of this chain process, however, is found to be several orders of magnitude smaller than expected.To explain this result, a 1,6-biradical .1-1-O2. is proposed to be generated in this chain reaction as the product-determining intermediate that predominantly fragments into 3O2 and two molecules of 1.Cyclization to dioxane 2 and transformation to benzophenone 3 occur at presumably less than 0.1percent from this biradical.The pathways leading to cyclobutanes (4) and α-tetralones (5) are also discussed.