Pinacolborane
Chemical compound
Pinacolborane is the borane with the formula (CH3)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.
01Use 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 (B2pin2):
- 2 (CH3)4C2O2BH → (CH3)4C2O2B-BO2C2(CH3)4 + H2
Sources and credits
This article is adapted from the Wikipedia article “Pinacolborane”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- HBpin.svg by Smokefoot, Public domain
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