Hydrofunctionalization

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



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
 * Hydrosilylation
 * Hydrometalation (including both transition or main group metal hydrides)
 * Hydroamination
 * (Olefin) hydration (addition of H2O across a double bond)
 * Hydroalkoxylation (also known as hydroetherification)
 * Hydrohalogenation
 * Hydrovinylation (including hydroarylation and olefin dimerization and others)
 * Hydroacylation
 * Hydroformylation (refers specifically to the addition of CHO and H using H2 and CO as reagents, also known as the oxo process)