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2‐Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents
Author(s) -
Yusubov Mekhman S.,
Postnikov Pavel S.,
Yusubova Roza Ya.,
Yoshimura Akira,
Jürjens Gerrit,
Kirschning Andreas,
Zhdankin Viktor V.
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700776
Subject(s) - chemistry , oxidizing agent , hypervalent molecule , reagent , dehydrogenation , pyridine , reactivity (psychology) , organic chemistry , polyketide , combinatorial chemistry , alcohol oxidation , alcohol , catalysis , medicine , alternative medicine , pathology , biosynthesis , enzyme
Two powerful hypervalent iodine(V) oxidants, DMP‐OTs (1‐tosyloxy‐1,1‐diacetoxy‐1 H ‐1λ 5 ‐benzo[ d ][1,2]iodoxol‐3‐one) and IBX‐OTs (1‐tosyloxy‐1‐oxo‐1 H ‐1λ 5 ‐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.