Hydrofunctionalization

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A hydrofunctionalization reaction is the addition of hydrogen and another univalent fragment (X) across a carbon-carbon or carbon-heteroatom multiple bond. [1] Often, the term hydrofunctionalization without modifier refers specifically to the use of the covalent hydride (H-X) as the source of hydrogen and X for this transformation. If other reagents are used to achieve the net addition of hydrogen and X across a multiple bond, the process may be referred to as a formal hydrofunctionalization.

Generic hydrofunctionalization reaction. Generic hydrofunctionalization reaction.png
Generic hydrofunctionalization reaction.

For terminal olefins (or acetylenes), the regioselectivity of the process can be described as Markovnikov (addition of X at the substituted end) or anti-Markovnikov (addition of X at the unsubstituted end). Catalysts are frequently employed to control the chemo-, regio-, and stereoselectivity of hydrofunctionalization reactions.

Examples

Some of the better known classes of hydrofunctionalization reactions include the following:

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References

  1. Hydrofunctionalization - Springer. Topics in Organometallic Chemistry. Vol. 43. 2013. doi:10.1007/978-3-642-33735-2. ISBN   978-3-642-33734-5.