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The reactivity of a boron complex with a redox-active formazanate ligand, LBPh 2 [L = PhNNC( p-tol)NNPh], was studied. Two-electron reduction of this main-group complex generates the stable, nucleophilic dianion [LBPh 2 ] 2- , which reacts with the electrophiles BnBr and H 2 O to form products that derive from ligand benzylation and protonation, respectively. The resulting complexes are anionic boron analogues of leucoverdazyls. N-C and N-H bond homolysis of these compounds was studied by exchange NMR spectroscopy and kinetic experiments. The weak N-C and N-H bonds in these systems derive from the stability of the resulting borataverdazyl radical, in which the unpaired electron is delocalized over the four N atoms in the ligand backbone. We thus demonstrate the ability of this system to take up two electrons and an electrophile (E + = Bn + , H + ) in a process that takes place on the organic ligand. In addition, we show that the [2e - /E + ] stored on the ligand can be converted to E • radicals, reactivity that has implications in energy storage applications such as hydrogen evolution.

inorganic chemistry

Reactivity of Two-Electron-Reduced Boron Formazanate Compounds with Electrophiles: Facile N–H/N–C Bond Homolysis Due to the Formation of Stable Ligand Radicals