An Efficient Procedure for the Synthesis of Crystalline Aryldiazonium Trifluoroacetates – Synthetic Applications

✍ Scribed by Christophe Colas; Maurice Goeldner

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 294 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199906)1999:6<1357::aid-ejoc1357>3.0.co;2-p

✦ Synopsis

We have developed a very mild procedure for the synthesis chemical shifts in diazonium salts. An excellent linear relationship emerged between Brown's substituent constants of crystalline aryldiazonium trifluoroacetate salts in high yields under anhydrous conditions. Over thirty mono-or s + p and the 13 C ipso chemical shifts. The diazonium salts obtained proved to be much more soluble in organic solvents polyfunctional aniline derivatives have been diazotized by this method, including water-and acid-sensitive substrates.

than their tetrafluoroborate counterparts. They were tested in Pd-mediated coupling reactions of various carbon-carbon The o-and p-hydroxyaryldiazonium salts, derived from the corresponding anilines, could be deprotonated by treatment double bonds, and were found to give good yields within short reaction times under very mild conditions. We believe with K 2 CO 3 to yield pure diazoquinones. NMR and UV/Vis spectra have been recorded for all the synthesized salts; the that diazonium trifluoroacetates represent a very attractive alternative to diazonium tetrafluoroborates. data are in good agreement with the rather limited published data and constitute a first extensive report of 13 C-NMR