- Source: Bis(pinacolato)diboron
- Bis(pinacolato)diboron
- Boronic acid
- Miyaura borylation
- Diazonium compound
- Borylation
- Pinacol
- Organoboron chemistry
- Catellani reaction
- Tetrahydroxydiboron
- Norio Miyaura
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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.
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) Ă….
Dehydrogenation of pinacolborane provides an alternative route:
2 (CH3)4C2O2BH → (CH3)4C2O2B-BO2C2(CH3)4 + H2
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:
CH3(CH2)6CH3 + [pinB]2 → pinBH + CH3(CH2)7Bpin
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.
References
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Bis(pinacolato)diboron - Wikipedia
Bis(pinacolato)diboron is a covalent compound containing two boron atoms and two pinacolato ligands. It has the formula [(CH 3 ) 4 C 2 O 2 B] 2 ; the pinacol groups are sometimes …
Bis(pinacolato)diboron 99 73183-34-3 - MilliporeSigma
Bis(pinacolato)diboron or (B 2 pin 2) 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 …
Bis(pinacolato)diboron | 73183-34-3 - ChemicalBook
27 Jan 2025 · Bis(pinacolato)diboron or (B 2 pin 2) is the most commonly used diborane reagent in organic synthesis due to its high stability in air and moisture. It can be synthesized by …
Bis(pinacolato)diborane | C12H24B2O4 | CID 2733548 - PubChem
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 …
Bis(pinacolato)diboron, 98+%, Thermo Scientific Chemicals
Bis(pinacolato)diboron is a reagent used for the cis-vicinal diborylation of acetylenes and olefins with platinum catalysis. It acts as a substrate used in a new palladium-catalyzed cyclization of …
Bis(pinacolato)diboron - 4,4 - MilliporeSigma
Bis(pinacolato)diboron. Synonyms: 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane. CAS 73183-34-3. Molecular Weight 253.94. Browse …
Bis(pinacolato)diboron: Synthesis and applications - ChemicalBook
25 Feb 2020 · Bis(pinacolato)diboron is an important organic intermediate. In Suzuki reaction, it has the advantages of high reaction selectivity, mild conditions, and high yield.