80334-07-2Relevant articles and documents
Copper catalysed Gomberg-Bachmann-Hey reactions of arenediazonium tetrafluoroborates and heteroarenediazonium o-benzenedisulfonimides. Synthetic and mechanistic aspects
Antenucci, Achille,Barbero, Margherita,Dughera, Stefano,Ghigo, Giovanni
, (2020/10/20)
Gomberg-Bachmann-Hey reactions were carried out in the presence of copper as a catalyst and gave rise to biaryls or heterobiaryls in good yields and in mild reaction conditions. A computational study of some key points of the reaction was performed. The results are coherent with the experimental data and confirm some aspects of the mechanism. The reaction free energies for the reduction in benzene by CuI of a set of 40 (hetero)arenediazonium tetrafluoroborates were calculated. Both the experiments and the calculations showed that in the coupling with substituted solvents (toluene, bromobenzene, nitrobenzene and anisole) the binding to the ortho position was always favoured.
Ni(II) catalyzed bromination of aryl C-H bonds
Bhattacharya, Moumita,Cluff, David B.,Das, Siddhartha
, p. 238 - 241 (2015/02/20)
Bromination of unactivated aromatic C-H bonds without directing and/or chelating groups was achieved by employing an air stable N-heterocyclic Ni(II) complex. PhI(OAC)2and N-bromosuccinimide have been used as the oxidizing agent and the bromine source, respectively. Yields for bromination are as high as >99%, especially in presence of electron-withdrawing groups like -NO2and -CF3. This is a rare report on C-H bond activation with Ni(II) where, instead of homo C-C coupling, reductive elimination to form C-halogen could be achieved.
