o-Iodoxybenzoic Acid (IBX) as a Viable Reagent in the Manipulation of Nitrogen- and Sulfur-Containing Substrates: Scope, Generality, and Mechanism of IBX-Mediated Amine Oxidations and Dithiane

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• 作者：K. C. Nicolaou ; Casey J. N. Mathison ; and Tamsyn Montagnon
• 刊名：Journal of the American Chemical Society
• 出版年：2004
• 出版时间：April 28, 2004
• 年：2004
• 卷：126
• 期：16
• 页码：5192 - 5201
• 全文大小：260K
• 年卷期：v.126,no.16(April 28, 2004)
• ISSN：1520-5126

文摘

o-Iodoxybenzoic acid (IBX), a highly versatile hypervalent iodine(V) reagent, was found toefficiently mediate the dehydrogenation of amines in addition to facilitating the oxidative cleavage ofdithioacetals and dithioketals. Through the development of relevant IBX-based protocols, a plethora ofuseful synthetic intermediates, including imines, oximes, ketones, and aromatic N-heterocycles, were foundto be readily accessible under notably mild conditions. Further investigation of these transformations led tothe elucidation of valuable mechanistic details, resulting in the conclusion that they proceed via ionic ratherthan single electron transfer (SET) pathways.