(en) The functionalization of aromatic halides or aromatic compounds bearing substituents like fluorosulfonate, by coupling with various nucleophiles in the presence of transition metals (Pd, Cu, Ni..) has become over the years the favoured method to build up new carbon-carbon or carbon-heteroatom bonds. However, this strategy requires the availability of brominated or iodinated derivatives (which are often expensive) or chlorinated compounds (which present a reduced reactivity). The triflates are a good alternative, though their price limits their use to specific, valuable products. We would like to present here our results in the preparation of aromatic diazo-ethers from anilines derivatives as well as a study of their reactivity in metal-catalysed coupling reactions. During our investigations, we have also prepared a diazoaminobenzene containing substrate. Although this compound was somewhat prepared by accident, we became rapidly interested in its unusual structure and eventually found it to be reactive under adjusted coupling conditions...
Dejeaifve, A. (2011). Preparation of aromatic diazo-ethers and study of their reactivity towards transition metals. https://hdl.handle.net/2078.5/38557