Silver Instead of Gold in Nitronyl Nitroxide Chemistry

A nitronyl nitroxide organosilver derivative─an accessible and effective partner for cross-coupling of aryl- and heteroaryl halides─is reported for the first time. The novel cross-coupling method is based on preparation of an organosilver reagent containing a bulky N-heterocyclic carbene ligand, namely, SIPrAgNN, and a catalytic system consisting of Pd2dba3·CHCl3 and phosphine ligand MeCgPPh having an adamantane-like framework. The newly developed protocol was found to be well-compatible with various aryl- and heteroaryl halides, thus expanding the scope of directed synthesis of functionalized nitronyl nitroxide radicals and high-spin molecules.