hydrofunctionalization

A hydrofunctionalization reaction is the addition of hydrogen and another univalent fragment (X) across a carbon-carbon or carbon-heteroatom multiple bond.{{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}} 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.

File:Generic hydrofunctionalization reaction.png

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.