Pinacolborane
Pinacolborane is the borane with the formula 4C2O2BH. Often pinacolborane is abbreviated HBpin. It features a boron hydride functional group incorporated in a five-membered C2O2B ring. Like related boron alkoxides, 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.Pinacolborane also affects catalyst-free hydroboration of aldehydes, ketones, and carboxylic acids.
Pinacolborane is used in borylation, a form of C-H activation.
Dehydrogenation of pinacolborane affords dipinacolatodiborane :
Related compounds
- Catecholborane