Nicolaou K C, Mathison Casey J N, Montagnon Tamsyn
Department of Chemistry and Skaggs Institute for Chemical Biology, Scripps Research Institute, La Jolla, California 92037, and Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093 USA.
J Am Chem Soc. 2004 Apr 28;126(16):5192-201. doi: 10.1021/ja0400382.
o-Iodoxybenzoic acid (IBX), a highly versatile hypervalent iodine(V) reagent, was found to efficiently mediate the dehydrogenation of amines in addition to facilitating the oxidative cleavage of dithioacetals and dithioketals. Through the development of relevant IBX-based protocols, a plethora of useful synthetic intermediates, including imines, oximes, ketones, and aromatic N-heterocycles, were found to be readily accessible under notably mild conditions. Further investigation of these transformations led to the elucidation of valuable mechanistic details, resulting in the conclusion that they proceed via ionic rather than single electron transfer (SET) pathways.
邻碘苯甲酸（IBX）是一种用途广泛的高价碘（V）试剂，除了能促进二硫缩醛和二硫缩酮的氧化裂解外，还被发现能有效介导胺的脱氢反应。通过开发相关的基于IBX的方法，人们发现大量有用的合成中间体，包括亚胺、肟、酮和芳族氮杂环，在显著温和的条件下很容易获得。对这些转化的进一步研究导致了有价值的机理细节的阐明，得出的结论是它们通过离子而非单电子转移（SET）途径进行。
