4.4 Article

Modified o-methyl-substituted IBX: room temperature oxidation of alcohols and sulfides in common organic solvents

Journal

TETRAHEDRON LETTERS
Volume 49, Issue 1, Pages 80-84

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.11.013

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o-Methyl-substituted Me-IBX is the first modified analog of IBX that oxidizes alcohols in common organic solvents at room temperature, due to a composite of two factors, that is, low solubility and hypervalent twisting-promoted rate enhancement. Furthermore, the reagent is efficient for selective oxidation of sulfides to sulfoxides, a transformation that otherwise occurs only sluggishly with standard IBX The facile synthetic accessibility and its mild as well as non-hazardous nature render Me-IBX a stable equivalent of Dess-Martin periodinane reagent in organic oxidations. (C) 2007 Elsevier Ltd. All rights reserved.

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