2-Iodoxybenzoic Acid Tosylates: the Alternative to Dess-Martin Periodinane Oxidizing Reagents

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Advanced Synthesis & Catalysis, ISSN: 1615-4150, Vol: 359, Issue: 18, Page: 3207-3216

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Mekhman S. Yusubov, Pavel S. Postnikov, Roza Ya. Yusubova, Akira Yoshimura, Gerrit Jürjens, Andreas Kirschning, Viktor V. Zhdankin
Chemical Engineering, Chemistry
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Two powerful hypervalent iodine(V) oxidants, DMP-OTs (1-tosyloxy-1,1-diacetoxy-1H-1λ-benzo[d][1,2]iodoxol-3-one) and IBX-OTs (1-tosyloxy-1-oxo-1H-1λ-benzo[d][1,2]iodoxol-3-one) show high reactivity in the oxidation of structurally complex primary and secondary alcohols, which are highly functionalized polyketide or terpene fragments or steroids. The yields of the corresponding carbonyl compounds are even higher for the protocol that uses pyridine as additive. The oxidations proceed very rapidly at room temperature leaving the protective groups and π-systems intact and affording the corresponding carbonyl compounds in good to excellent yields. Moreover, IBX-OTs is an efficient reagent for the oxidative dehydrogenation of steroidal alcohols to the corresponding enones. (Figure presented.).

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