Hypervalent Iodine Reagents

Hypervalent Iodine Reagents

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  • General Characteristics

Iodine can exist in high valence states because of its higher polarizability and smaller electronegativity compared with other halogen elements.

Hypervalent iodine compounds are readily reduced to stable monovalent state with the dissociation of apical groups, thus they act as good oxidizing agents.

Synthetically useful trivalent iodine reagents (λ3-iodane) include the following:


Pentavalent iodine (λ5-iodane) and higher valence states (such as iodine(VII)) are also known, among which the Dess-Martin reagent and periodate salt are commonly used as mild oxidizing agents.

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  • Reaction Mechanism

The reactivity of hypervalent iodine compounds generally increases with the degree of how easily the apical groups dissociate.

  • Examples

Asymmetric oxidation using a chiral hypervalent iodine reagent.[1]


Progress has been made in recent years to reduce the amount of iodine reagents to substoichiometric.

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  • References

(1) Dohi, T.; Maruyama, A.; Takenaga, N.; Senami, K.; Minamitsuji, Y.; Fujioka, H.; Carmmerer, S. B.; Kita, Y. Angew. Chem. Int.Ed. 2008, 47, 3787. doi:10.1002/anie.200800464

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