Hydration of Olefins, Dienes, and Acetylenes via Hydroboration

Zweifel, George; Brown, Herbert C.


The hydroboration of olefins, dienes, and acetylenes involves the addition of a boron-hydrogen bond to the carbon-carbon multiple bond. This reaction provides a new, convenient route to the corresponding organoboranes and makes them readily available as intermediates in organic synthesis. One of the important reactions that the organoboranes undero is the rapid and essentially quantitative oxidation with alkaline hydrogen peroxide. The hydroboration of olefins involves a cis addition of the boron hydrogen bond, the boron atom becoming attached to the less substituted of the two olefinic carbon atoms of the double bond.

This chapter surveys the available information on the hydration of olefins, dienes, acetylenes, and their derivatives by the hydroboration-oxidation procedure.