Organoboranes, oxidation

Hydroboration-oxidation is now a standard method for anb -Markovnikov s cis-hydration [1] of alkenes from the less hindered side of the double bond. The hydroboration of olefins, mainly in THF solvent, affords conveniently the corresponding organoboranes. Oxidation of the intermediate organoboranes is most conveniently carried out by successive addition of 3 M NaOH and 30% hydrogen peroxide (depicted as [O], Eq. 6.1). Other oxidation procedures, e.g., HjOj in buffer solutions, HjOj in NaOAc, per acids, and trimethyl-N-oxides are used in certain cases when the organoboranes are unstable to water or contain functionalities sensitive to alkaline medium. 

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