Bis(pinacolato)diboron is a covalent compound containing two boron atoms and two pinacolato ligands. It has the formula [(CH3)4C2O2B]2; the pinacol groups are sometimes abbreviated as "pin", so the structure is sometimes represented as B2pin2.
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, B2pin2 is not moisture-sensitive and can be handled in air.
- Reagent used for the synthesis of aryl, alkenyl, allyl and alkylboronic esters.
- Reagent used for the borylation of an α,β-unsaturated ketones.
- Reagent used for the synthesis of precursors for conducting polymers.
- Reagent used for the synthesis of in vivo fluorescent probes.
- Reagent used for the diborylation of alkynes.
Bis(pinacolato)diboron may be prepared by reacting tetrakis(dimethylamino)diboron with pinacol in acidic conditions. The B-B bond length is 1.711(6) Å.
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: CH3(CH2)6CH3 + [pinB]2 → pinBH + CH3(CH2)7Bpin These reactions proceed via boryl complexes.
In the Suzuki reaction, Bis (pinacolato) diboron has the advantages of high reaction selectivity, mild conditions, and high yield. For some compounds that are unstable or need to improve the selectivity of the reaction, Bis (pinacolato) diboron and aryl halide are used. React is a good choice.
Bis(pinacolato)diboron is a white crystal powder, It is commonly used coupling reagent.
As a boron source in Pt-mediated diborations, coupling reactions; in Rh-or Ir-mediated borylations of alkanes and arenes, and in carbenoid chemistry.
Bis(pinacolato)diboron is used as a condensation agent in the preparation poly(arylene)s. Bis(pinacolato)diboron is an organoboranate with potential use as matrix metallo-proteinase (MMP-2) inhibitor.
ChEBI: Bis(pinacolato)diboron is a 1,3,2-dioxaborolane that is 4,4,5,5-tetramethyl-1,3,2-dioxaborolane in which the boron hydrogen at position 2 is replaced by a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group. It is a reagent used in organic synthesis to synthesise pinacol boronic esters. It has a role as an EC 3.4.24.24 (gelatinase A) inhibitor.
Bis(pinacolato)diboron or (B2pin2) is the most commonly used diborane reagent in organic synthesis due to its high stability in air and moisture. It can be synthesized by treating tetrakis(dimethylamino)diboron with pinacol in acidic conditions.
