41075-28-9Relevant academic research and scientific papers
An efficient procedure for the synthesis of crystalline aryldiazonium trifluoroacetates - Synthetic applications
Colas, Christophe,Goeldner, Maurice
, p. 1357 - 1366 (2007/10/03)
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.
