Bis(pinacolato)diboron
Bis(pinacolato)diboron is a covalent compound containing two boron atoms and two pinacolato ligands. It has the formula [(CH)COB]; the pinacol groups are sometimes abbreviated as "pin", so the structure is sometimes represented as Bpin. It is a colourless solid that is soluble in organic solvents. It is a commercially available reagent for making pinacol boronic esters for organic synthesis. Unlike some other diboron compounds, Bpin is not moisture-sensitive and can be handled in air. Preparation and structure. This compound may be prepared by treating tetrakis(dimethylamino)diboron with pinacol in acidic conditions. The B-B bond length is 1.711(6) Å.  Dehydrogenation of pinacolborane provides an alternative route: Reactions. The B-B bond adds across alkenes and alkynes to give the 1,2-diborylated alkanes and alkenes. Using various organorhodium or organoiridium catalysts, it can also be installed onto saturated hydrocarbons: These reactions proceed via boryl complexes. Bis(pinacolato)diboron can also be used as reducing agent for example in transition metal catalyzed hydrogenations of alkenes and alkynes.