Definition: What is Hydroboration-Oxidation?

The hydroboration-oxidation reaction is an organic chemical reaction that is used for the conversion of alkene into alcohol. In this reaction, borane (BH₃) is added across the carbon‐carbon double bond of an alkene resulting in an organoboron compound. This organoboron compound reacts with hydrogen peroxide in a basic medium (e.g., NaOH) and oxidizes to alcohol. The regiochemistry of this reaction is such that the product formed during hydroboration follows anti-Markovnikov’s rule, i.e., hydrogen goes to the more substituted carbon atom of the alkene. The stereochemistry of this reaction is syn, i.e., hydrogen and boron are on the same side of the product ^[1-6].

The history of the hydroboration reaction goes back to the last 1950s when Nobel laureate Herbert C. Brown reported his findings while working at Purdue University.

Examples of Hydroboration-Oxidation

Mechanism of Hydroboration-Oxidation ^[6-10]

References
1. Definition – Byjus.com
2. Definition – Cliffsnotes.com
3. Definition – Chem.ucla.edu
4. Definition – Masterorganicchemistry.com
5. Definition – Chem.ucla.edu
6. Definition and mechanism – Chem.libretexts.org
7. Mechanism – Masterorganicchemistry.com
8. Mechanism – Chem.ucalgary.ca
9. Mechanism – Chem.ucalgary.ca
10. Mechanism – Organic-chemistry.org