Bis(pinacolato)diboron

Description

Bis(pinacolato)diboron is typically used for making pinacol boronate esters. These boronates are generally used subsequently in palladium catalyzed Suzuki couplings. They are also sometimes used in other reactions such as oxidations to form phenols. Pinacol boronate esters are generally easier to handle than boronic acids.

Chemical properties

Bis(pinacolato)diboron is a white crystal powder, It is commonly used coupling reagent.

The Uses of Bis(pinacolato)diboron

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.

The Uses of Bis(pinacolato)diboron

The Iodo compound (308 mg, 0.513 mmol), the boronic ester (194 mg, 0.641 mmol), K3PO4 (327 mg, 1.539 mmol), XPhos (14.67 mg, 0.031 mmol), and Pd2(dba)3 (14.09 mg, 0.015 mmol) were combined in a microwave vial. The vial was purged with argon, after which time was added dioxane (3 mL) and H2O (0.5 mL) The reaction was irradiated in a microwave reactor at 120 C for 10 min. Additional boronic ester (50 mg) was added and the mixture was irradiated at 120 C for another 10 min. The mixture was then treated with aq 1N NaOH and extracted with EtOAc (50 mL). The org layer was dried (MgSO4), concentrated, and purified by flash chromatography (20% MeOH/DCM) to provide the product as a dark yellow solid. [177 mg, 53%]

The Uses of Bis(pinacolato)diboron

suzuki reaction

The Uses of Bis(pinacolato)diboron

As a boron source in Pt-mediated diborations, coupling reactions; in Rh-or Ir-mediated borylations of alkanes and arenes, and in carbenoid chemistry.

What are the applications of Application

Bis(pinacolato)diboron is a reagent used for the cis-vicinal diborylation of acetylenes and olefins with Pt catalysis; borylation of aromatics by Pd catalysis

Definition

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.

General Description

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.