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A plethora of natural products exist that contain characteristic vicinal 1,2-diols in their scaffolds. The alkene dihydroxylation methodology developed by Sharpless continues to be the most robust and general method to obtain this important motif. However, the main problem with this transformation is the use of osmium as the catalyst and, since the 1990s, various methods have been developed that employ alternative transition metals. In this chapter, the most important protocols for the racemic and enantioselective dioxygenation of alkenes mediated by metals are summarized, together with recently developed methods that employ chiral nonracemic hypervalent iodine(III) reagents.

The oxidation of amines and hetarenes are significant transformations that have been widely applied in synthetic organic chemistry. In this chapter, the oxidation of primary, secondary, and tertiary amines, affording imines, nitriles, amides, carbonyls, oximes, nitro compounds, diazenes and their oxides, nitrones, hydrazines, and N-oxides, as well as the oxidation of hetarenes including pyridines, azoles, pyrroles, indoles, guanines, and adenines, are comprehensively discussed. In addition to traditional organometallic catalysis to fulfill these oxidation reactions, some advanced approaches such as photocatalysis, biochemical catalysis, and biomimetic catalysis are also described.

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