Pinacolborane is the
borane
Borane is an inorganic compound with the chemical formula . Because it tends to dimerize or form adducts, borane is very rarely observed. It normally dimerizes to diborane in the absence of other chemicals. It can be observed directly as a c ...
with the formula (CH
3)
4C
2O
2BH. Often pinacolborane is abbreviated HBpin. It features a boron hydride functional group incorporated in a five-membered C
2O
2B ring. Like related boron
alkoxide
In chemistry, an alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They are written as , where R is the organyl substituent. Alkoxides are strong bases and, whe ...
s, pinacolborane is monomeric. It is a colorless liquid. It features a reactive B-H functional group.
[
]
Use in organic synthesis
In the presence of catalysts, pinacolborane hydroborates alkenes and, less rapidly, alkynes.borylation
Metal-catalyzed C–H borylation reactions are transition metal catalyzed organic reactions that produce an organoboron compound through functionalization of aliphatic and aromatic C–H bonds and are therefore useful reactions for carbon–hydroge ...
, a form of C-H activation.
Dehydrogenation of pinacolborane affords dipinacolatodiborane (B2pin2):
Related compounds
*Catecholborane
Catecholborane (abbreviated HBcat) is an organoboron compound that is useful in organic synthesis. This colourless liquid is a derivative of catechol and a borane, having the formula C6H4O2BH.
Synthesis and structure
Traditionally catecholborane ...
References
Boronate esters