6629-83-0

Upstream product

• 67-56-1 methanol 
• 66184-02-9 4,4',4''-(2-bromoethene-1,1,2-triyl)tris(1-methylbenzene) 
• 624-31-7 4-tolyl iodide 
• 1066-54-2 trimethylsilylacetylene 
• 108-88-3 toluene 
• 35675-44-6 4-methylphenylacetyl chloride 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 766-97-2 4-n-methylphenylacetylene 
• 60126-95-6 p-tolylazoxy p-tolyl sulphone 
• 51490-06-3 1,2-di-p-tolyl-ethanone 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 611-97-2 bis(p-methylphenyl)-methanone 
• 696-61-7 4-tolylmagnesium chloride 
• 112323-95-2 1,1,2-tri-p-tolyl-ethanol 

Downstream Products

• 62155-49-1 1,1,2-tri-p-tolyl-ethane 

Relevant academic research and scientific papers

Synthesis of vinylgermanes via the Au/TiO2-catalyzed cis-1,2-digermylation of alkynes and the regioselective hydrogermylation of allenes

In the presence of Au/TiO2 (1 mol %), terminal alkynes react quantitatively with stoichiometric amounts of the unactivated digermane Me3Ge-GeMe3, forming exclusively cis-1,2-digermylated alkenes. We also establish the Au/TiO2-catalyzed hydrogermylation of terminal allenes with Et3GeH, which exhibits a highly regioselective mode of addition on the more substituted double bond forming vinylgermanes. Additionally, we provide preliminary results regarding the Pd nanoparticle-catalyzed C-C coupling of 1,2-digermyl alkenes with aryl iodides.

Unexpected and powerful effect of chlorobenzene in direct palladium-catalyzed cascade Sonogashira-hydroarylation reaction

A ubiquitous accelerating effect of chlorobenzene (PhCl) was observed unexpectedly in the Pd-catalyzed cascade Sonogashira-hydroarylation reaction. This new type of carbon-carbon bond forming cross-coupling reaction was efficiently catalysed by Pd2(dba)3 in the presence of a catalytic amount of PhCl, which provides a facile and direct approach to the synthesis of trisubstituted olefins.

Palladium-catalyzed desulfitative hydroarylation of alkynes with sodium sulfinates

A palladium-catalyzed desulfitative hydroarylation of alkynes with aryl sulfinic acid sodium salts is described. The reaction showed good regio- and stereoselectivity, and afforded the hydroarylation products in good yields. Various functional groups were well tolerated under the optimized reaction conditions.

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.

Palladium-catalyzed reactions of aryl iodides with trimethylsilylacetylenes and disubstituted alkynes: The synthesis of diarylacetylenes and triarylethylenes

Treatment of 2.5 equiv. of aryl iodide with trimethylsilylacetylene in the presence of 3 equiv. of sodium methoxide and 5 mol% of Pd(PPh3)4 under refluxing methanol for 6 h gave diarylacetylene in good chemical yields. When the catalyst was replaced by Pd(dba)2 and 5 equiv. of aryl iodide were added under the same reaction conditions, triarylethylenes were obtained in 70-85% yields. Only the sterically hindered o-methoxyiodobenzene and 2-iodothiophene gave the diarylacetylene, but also in good chemical yield. Reaction of aryl iodides with disubstituted alkynes in the presence of Pd(OAc)2 and sodium methoxide in methanol produced trisubstituted ethylenes in modest to good yields. The hydrogenolysis of the organopalladium is proposed through β-hydride elimination of the palladium methanolate intermediates.

Lithium aluminium hydride reduction of some triarylvinyl bromides and acetates catalyzed by some transition metal chlorides

A number of triarylvinyl halides and acetates were reduced with lithium aluminium hydride using various transition metal chlorides as catalysts.The vinylic halides were reduced to the corresponding alkenes while the vinylic acetates were reduced to mixtures of triarylketones and alcohols.The reduction of labeled vinylic halides did not result in any scrambling of the label from C-2 to C-1.The reactions took place under mild conditions and relativley fast reaction times.

Reactions of Azo and Azoxy Sulphones with Transition Metal Complexes. Part 7. Arylation of Olefins with Arylazoxy Aryl Sulphones Catalysed by a Palladium(0) Phosphine Complex

The arylation of acyclic and cyclic olefins by arylazoxy aryl sulphones has been investigated in the presence of a palladium(0) catalyst in benzene.Both of the aryl groups of the arylazoxy aryl sulphones are found to participate in the arylation.Two equivalents of aryl-substituted olefins were obtained when the reactions were carried out at 80 deg C, whereas one equivalent of olefin was arylated at 120 deg C.A plausible catalytic cycle involving a diarylpalladium(II) species is proposed.

Degenerate β-Aryl Rearrangements in Photochemically Generated Triarylvinyl Cations

Irradiation of triphenyl- (1a), tri-p-tolyl (1b),or tri-p-anisylvinyl bromide (1c) in methanol gave the vinyl ethers 4 and the phenanthrenes 5.A study of -labeled bromides showed that β-aryl rearrangements takes place in the photochemically generated vinyl cations 3*.Irradiation of triaryl bromides 1* in trifluoroethanol and analysis of the extent of scrambling from C-2 to C-1 in the trifluoroethyl vinyl ethers 8 showed 38percent, 72percent, and 92percent rearrangement of the 13C label for 1a*, 1b*, and 1c*, respectively.Similar irradiation of 1* in methanol resulted in no rearrangement in 4.The results are discussed in relation to the nature of the solvent, the stability of the triarylvinyl cations, and the migratory aptitudes of the aryl groups.The behavior of the photochemically and thermally generated ions was compared.