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How does hydroboration add boron and hydrogen across a carbon-carbon double bond?
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organometallic compound
The periodic table of the elements, displaying the group numbers and the s, p, d, and f blocks. Elements in the shaded area are the metals of organometallic chemistry.
Hydroboration is a chemical reaction in which a boron-hydrogen compound, typically of the type , adds across the carbon-carbon double bond of an alkene or alkyne to form an organoborane.12
Developed by the chemist Herbert C. Brown, the reaction is characterized by its regioselectivity, which is opposite to the Markovnikov rule. In this process, the boron atom and the hydrogen atom add to the double bond such that the net result—often followed by oxidation with hydrogen peroxide—is the addition of H and –OH across the bond in an anti-Markovnikov fashion.2
The reaction is highly efficient, often proceeding quantitatively at room temperature in ether solvents, and has become a vital tool for stereospecific organic synthesis.1