2362-70-1

Upstream product

• 60126-95-6 p-tolylazoxy p-tolyl sulphone 
• 142-29-0 cyclopentene 
• 33604-67-0 (4-methylphenyl)azo 4-methylphenyl sulfone 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 1190899-34-3 (E)-1-(2-cyclopropylvinyl)-4-methylbenzene 
• 106-49-0 p-toluidine 
• 49724-60-9 (p-toluene)diazonium trifluoroacetate 

Relevant academic research and scientific papers

Mechanism of the Ni(0)-catalyzed vinylcyclopropane-cyclopentene rearrangement

(Chemical Equation Presented) A combination of physical organic experiments and quantum chemical calculations were used to construct a detailed mechanistic model for the Ni(0)-N-heterocyclic carbene-catalyzed vinylcyclopropane- cyclopentene rearrangement

Arenediazonium o-benzenedisulfonimides as efficient reagents for Heck-type arylation reactions

Arenediazonium o-benzenedisulfonimides can be used as new and efficient reagents for Heck-type arylation reactions of some common substrates containing C-C multiple bonds, namely ethyl acrylate, acrylic acid, acroleyne, styrene and cyclopentene. The reactions were carried out in an organic solvent, in the presence of Pd(OAc)2 as pre-catalyst, and gave rise to arylated products, for example, ethyl cinnamates, cinnamic acids, cinnamic aldehydes and stilbenes, possessing an (E)-configuration, and 1-arylcyclopentenes, in good to excellent yields. It is noteworthy that all the reactions led to the recovery, in greater than 80% yield, of o-benzenedisulfonimide, recyclable for the preparation of other diazonium salts.

An efficient procedure for the synthesis of crystalline aryldiazonium trifluoroacetates - Synthetic applications

We have developed a very mild procedure for the synthesis of crystalline aryldiazonium trifluoroacetate salts in high yields under anhydrous conditions. Over thirty mono- or polyfunctional aniline derivatives have been diazotized by this method, including water- and acid-sensitive substrates. The o- and p-hydroxyaryldiazonium salts, derived from the corresponding anilines, could be deprotonated by treatment with K2CO3 to yield pure diazoquinones. NMR and UV/Vis spectra have been recorded for all the synthesized salts; the data are in good agreement with the rather limited published data and constitute a first extensive report of 13C-NMR chemical shifts in diazonium salts. An excellent linear relationship emerged between Brown's substituent constants S+(p) and the 13C(ipso) chemical shifts. The diazonium salts obtained proved to be much more soluble in organic solvents than their tetrafluoroborate counterparts. They were tested in Pd-mediated coupling reactions of various carbon-carbon double bonds, and were found to give good yields within short reaction times under very mild conditions. We believe that diazonium trifluoroacetates represent a very attractive alternative to diazonium tetrafluoroborates.

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.

Arylation of Olefins by Arylazo Aryl Sulfones under Palladium(0) Catalysis

Palladium(0)-catalyzed reaction of arylazo aryl sulfones with olefins in benzene at 80 deg C gave aryl-substituted olefins in good yield.Diarylpalladium(II) species was proposed as an intermediate in this reaction.

A HYBRID BIRCH-CLAISEN METHODOLOGY FOR ARYLATION AT ALLYLIC TERMINI: SYNTHESIS OF (+/-)-HERBERTENE

A hybrid Birch-Claisen methodology has been developed for the regio- and stereo-controlled arylation of allyl groups, and applied to a synthesis of (+/-)-herbertene.

REACTION OF DIAZONIUM SALTS WITH TRANSITION METALS-III. PALLADIUM(0)-CATALYZED ARYLATION OF UNSATURATED COMPOUNDS WITH ARENEDIAZONIUM SALTS

Palladium (0) catalyzed reactions of arenediazonium salts for arylation of aliphatic and cyclic olefins and allylic alcohols, styrene and ethyl acrylate were studied.Effect of the olefinic compounds and other reaction variables on the arylation were presented.Arylpalladium species was proposed as the most plausible intermediated in this reaction.