13392-76-2

Upstream product

• 66821-18-9 ethyl-(1-p-tolyl-vinyl)-ether 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 122-00-9 para-methylacetophenone 
• 6293-68-1 bis(4-methylphenyl)iodonium bromide 
• 768-60-5 4-methoxyphenylacetylen 
• 856382-04-2 2-bromo-1-ethoxy-1-(4-methylphenyl)ethane 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 766-97-2 4-n-methylphenylacetylene 
• 637-69-4 4-Methoxystyrene 
• 106-43-4 para-chlorotoluene 
• 60672-33-5 (E)-4-methyl-N'-(1-(p-tolyl)ethylidene)benzenesulfonohydrazide 
• 1228679-43-3 (E)-N′-(1-(4-methoxyphenyl)ethylidene)-4-methylbenzenesulfonohydrazide 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 60665-82-9 Methyl-p-anisyl-p-tolylcarbenium-Ion 
• 196489-67-5 1-(1-(4-methoxyphenyl)ethyl)-4-methylbenzene 
• 23886-71-7 4-methoxy-4'-methylbenzophenone 

Relevant academic research and scientific papers

Regiodivergent DH or HD Addition to Alkenes: Deuterohydrogenation versus Hydrodeuterogenation

The regioselective and regiodivergent addition of H-D to a variety of 1,1-diarylalkenes was realized utilizing selectively deuterated dihydroaromatic compounds, which were generated by cobalt catalysis. The reaction was initiated by catalytic amounts of B

Toward a Greener Barluenga-Valdés Cross-Coupling: Microwave-Promoted C-C Bond Formation with a Pd/PEG/H2O Recyclable Catalytic System

A green Barluenga-Valdés cross-coupling reaction for the synthesis of 1,1-diarylethylenes using palladium catalysis has been developed. The new catalytic system based on Pd/Xphos-SO3Na or Pd/MeDavephos-CF3SO3 in PEG/H2O under microwave irradiation was found to be the best conditions for this transformation. The recyclability of the palladium catalyst system was also studied, and it was found to be active over nine runs without significant loss in its activity.

Traceless directing group mediated branched selective alkenylation of unbiased arenes

Owing to the synthetic importance of branched olefinated products, we report palladium catalyzed formation of branched olefins facilitated by a C-H activation based protocol. This involves selective insertion of olefins and subsequent decarboxylation using a completely unbiased benzene ring as the starting precursor. The significance of the protocol has been further highlighted by exhibition of functionality tolerance along with a late-stage modification of the branched olefinated products leading to the formation of other functionalized molecules.

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.

Evidences of release and catch mechanism in the Heck reaction catalyzed by palladium immobilized on highly cross-linked-supported imidazolium salts

Palladium (10 wt%) on a highly cross-linked imidazolium-based material was used as catalyst in 0.1 mol% in the Heck reaction between several alkenes and aryl iodides. Products were obtained from good to high yields. Deeper investigations showed a release of Pd species in solution and their capture by the imidazolium-based support. When a sixfold amount of support was employed the re-captured Pd species (0.5-0.6 wt%) were not anymore catalytically active. This result represents a new interesting aspect of this work since the highly cross-linked imidazolium-based material can act also as Pd scavenger avoiding the release of the metal in solution. Important differences between Heck and Suzuki reactions have been evidenced when the reactions were carried out in the presence of the scavenging support.

Selective arylation and vinylation at the α position of vinylarenes

In intermolecular Heck reactions of styrene and vinylarenes, the aryl and vinyl groups routinely insert at the β position. However, selective insertion at the α position has been very rare. Herein, we provide a missing piece in the palette of Heck reaction, which gave >20:1 α selectivity. The key to our success is a new ferrocene 1,1′-bisphosphane (dnpf) that carries 1-naphthyl groups. Our mechanistic studies revealed that the high α selectivity is partly attributable to the steric effect of dnpf. The rigid and bulky 1-naphthyl groups of dnpf sterically disfavor β insertion. What the Heck! In intermolecular Heck reactions, insertion at the β position of aromatic olefins is very common, but reversal of the selectivity for selective α insertion has been a longstanding problem. A general method to couple aryl and vinyl triflates with aromatic olefins in >20:1 α selectivity is presented. The key to this successful approach is a new ferrocene bisphosphane with naphthyl groups on the phosphorus atom (see scheme; OTf=triflate). Copyright

Palladium catalyzed coupling of tosylhydrazones with aryl and heteroaryl halides in the absence of external ligands: Synthesis of substituted olefins

Palladium catalyzed cross-coupling reaction of hydrazones with aryl halides in the absence of external ligand is reported. The versatility of this coupling reaction is demonstrated in showcasing the selectivity of coupling reaction in the presence of hydr

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.

Microwave-assisted, Pd(0)-catalyzed cross-coupling of diazirines with aryl halides

Pd(0)-catalyzed cross-coupling reactions of diazirines with aryl halides under microwave heating conditions afford a series of substituted olefins. A reaction mechanism involving the migratory insertion of the Pd carbene intermediate is proposed.

Atom-efficient vinylic arylations with triarylbismuths as substoichiometric multicoupling reagents under palladium catalysis

The first atom-efficient arylation of vinylic iodides was achieved by using triarylbismuths as substoichiometric multicoupling reagents under palladium catalysis. Vinylic iodides were efficiently coupled with electronically divergent triarylbismuths to furnish the corresponding arylated products in short reaction times.