# 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.<ref>{{Cite book|title=Hydrofunctionalization - Springer|volume = 43|doi=10.1007/978-3-642-33735-2|series = Topics in Organometallic Chemistry|year = 2013|isbn = 978-3-642-33734-5}}</ref>  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''.

center|400x400px|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:

*[Hydroboration](/source/Hydroboration)
*[Hydrosilylation](/source/Hydrosilylation)
*[Hydrometalation](/source/Hydrometalation) (including both transition or main group metal hydrides)
*[Hydroamination](/source/Hydroamination)
*(Olefin) [hydration](/source/Hydration_reaction) (addition of H<sub>2</sub>O across a double bond)
*[Hydroalkoxylation](/source/Hydroalkoxylation) (''also known as'' hydroetherification)
*[Hydrohalogenation](/source/Hydrohalogenation)
*[Hydrovinylation](/source/Hydrovinylation) (including hydroarylation and olefin dimerization and others)
*[Hydroacylation](/source/Hydroacylation)
*[Hydroformylation](/source/Hydroformylation) (refers specifically to the addition of CHO and H using H<sub>2</sub> and CO as reagents, ''also known as'' the oxo process)

== References ==
{{reflist}}

Category:Addition reactions

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