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Relevant academic research and scientific papers

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.

IMPROVED PROCEDURES FOR THE PALLADIUM-CATALYZED INTERMOLECULAR ARYLATION OF CYCLIC ALKENES

Improved procedures for the palladium-catalyzed, intermolecular, allylic crosscoupling of aryl halides and cyclic alkenes inhibit double-bond isomerization and accommodate many important functional groups.

74. Solvolysis Mechanism of cis- and trans-2-Arylcyclopentyl p-Toluenesulfonates. Subsequent Step in cis-2-Arylcyclopentyl p-Toluenesulfonate Solvolysis

The solvolysis of a series of 1-deuteriated, 2-deuteriated, and undeuteriated cis-2-arylcyclopentyl p-toluenesulfonates in HCOOH, AcOH, and EtOH has been studied.We have shown that the classical secondary carbocation arising from substrate ionisation undergoes two concurrent processes, namely kc (direct products formation) and kip (hydrogenium bridged ion formation as tertiary carbocation or products precursor).The intrinsic properties of solvent and the aryl substituent electronic effects only affect the total solvolysis rate and the respective contributions of kc and kip processes.Comparing the observed and calculated kinetic isotope effects of D-C(2) allows one to conclude that no step can be called 'rate-determining step' but that the steps following ionisation have a preponderent effect on the total solvolysis rate.

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.

DIRECT TRANSFORMATION OF ARYLAMINES TO ALKENYLARENES UNDER PALLADIUM(0) CATALYSIS

Olefins could be arylated in good yields by the combination of arylamines (substituted anilines: 4-Me, 4-Cl, 4-Br, 2-NO2, 4-NO2, and 3-aminopyridine) and t-butyl nitrite under palladium(0) catalysis.