Hydroboration-Oxidation (HBO)

Rarely Tested


$$\text{R--CH=CH}_2 \xrightarrow{1) \, \text{B}_2\text{H}_6 / \text{THF} \quad 2) \, \text{H}_2\text{O}_2 / \text{OH}^-} \text{R--CH}_2\text{--CH}_2\text{OH}$$

Concept: A two-step synthetic pathway to convert alkenes into primary or less-substituted alcohols.

Step 1 (Hydroboration): Diborane [$$\text{B}_2\text{H}_6$$or$$\text{BH}_3\cdot\text{THF}$$].

Step 2 (Oxidation): Hydrogen peroxide [$$\text{H}_2\text{O}_2$$] in alkaline medium [$$\text{OH}^-$$].

Yields Anti-Markovnikov addition of water ($$\text{OH}^-$$attaches to the less sterically hindered carbon atom). Proceeds via a concerted 4-membered cyclic transition state resulting in syn-addition of $$\text{H}$$ and $$\text{OH}$$. No carbocation rearrangement occurs.

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