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A compound with a boron-boron triple bond is shown to undergo stepwise hydroboration reactions with catecholborane to yield an unsymmetrical hydro(boryl)diborene and a 2,3-dihydrotetraborane. Abstraction of H– from the latter compound produces an unusual cationic, planar tetraborane with a hydrogen atom bridging the central B2 moiety. Spectroscopic and crystallographic data and DFT calculations support a ‘protonated diborene’ structure for this compound, which can also be accessed via direct protonation of the corresponding diborene.
An N-heterocyclic-carbene-stabilized diboryne undergoes rapid, high-yielding and catalyst-free hydroamina- tion reactions with primary amines, yielding 1-amino-2-hydro- diborenes, which can be considered boron analogues of enamines. The electronics of the organic substituent at nitrogen influence the structure and further reactivity of the diborene product. With electron-rich anilines, a second hydroamination can occur at the diborene to generate 1,1-diamino-2,2-dihy- drodiboranes. With isopropylamine, the electronic influence of the alkyl substituent upon the diborene leads to an unprece- dented boron-mediated intramolecular N-dearylation reaction of an N-heterocyclic carbene unit.