I was wondering if there would be any problem using THF with a diazonium salt? I am reacting somewhat hydrophobic aryl diazonium salts with very hydrophobic arylamines, so the standard aqueous acid conditions don't work. I have had some success AcCN for the diazonium salt formation, and adding it to NMP/pyridine (to buffer the pH), but there seems to be a slow decomposition reaction with NMP lowering the yield, and AcCN is a poor solvent for the substrate, though it is good for the N2+ salt.
I'm going to try THF, but I just wanted to see if there was any consensus on THF, or other non traditional organic solvents for diazonium coupling reactions.
A phase transfer system might potentially work given the polarities as well. I am trying to find some literature on that.