Oxidative Dearomatization of Phenols: Why, How and What For?

Abstract

This account reviews our investigations over the last ten years on the selective dearomatization of phenols into cyclohexadienones and its application in natural products synthesis. 7Understanding Dimerization: Cieplak or Not Cieplak? 7.1Total Synthesis of (+)-Aquaticol 7.2Toward an All-Embracing Rationale! 8Conclusions and Perspectives

Commemorating Two Centuries of Iodine Research: An Interdisciplinary Overview of Current Research

“…The oxidative dearomatization of phenols to cyclohexadienones is readily achieved with iodine(III) reagents or IBX, [46] delivering intermediates that are useful in natural product synthesis. [47] Other common transformations mediated by hypervalent iodine include oxidative aryl coupling reactions, dehydrogenation of ketones, aziridination, epoxidation, rearrangements, fragmentations, and deprotection of dithianes.…”

Chemistry of Polyvalent Iodine

“…Numerous reviews on specific classes of polyvalent iodine compounds and their synthetic applications have recently been published 18–61. Most notable are the specialized reviews on [hydroxy(tosyloxy)iodo]benzene,41 the chemistry and synthetic applications of iodonium salts,29,36,38,42,43,46,47,54,55 the chemistry of iodonium ylides,56–58 the chemistry of iminoiodanes,28 hypervalent iodine fluorides,27 electrophilic perfluoroalkylations,44 perfluoroorgano hypervalent iodine compounds,61 the chemistry of benziodoxoles,24,45 polymer-supported hypervalent iodine reagents,30 hypervalent iodine-mediated ring contraction reactions,21 application of hypervalent iodine in the synthesis of heterocycles,25,40 application of hypervalent iodine in the oxidation of phenolic compounds,32,34,50–53,60 oxidation of carbonyl compounds with organohypervalent iodine reagents,37 application of hypervalent iodine in (hetero)biaryl coupling reactions,31 phosphorolytic reactivity of o -iodosylcarboxylates,33 coordination of hypervalent iodine,19 transition metal catalyzed reactions of hypervalent iodine compounds,18 radical reactions of hypervalent iodine,35,39 stereoselective reactions of hypervalent iodine electrophiles,48 catalytic applications of organoiodine compounds,20,49 and synthetic applications of pentavalent iodine reagents 22,23,26,59…”

Zweihundert Jahre Iodforschung: ein interdisziplinärer Überblick über die derzeitige Forschung

“…Die oxidative Desaromatisierung von Phenolen zu Cyclohexadienonen kann leicht mit Iod(III)-Reagentien oder IBX erreicht werden, [46] was Zwischenprodukte liefert, die für die Naturstoffsynthese geeignet sind. [47] Andere typischerweise von hypervalentem Iod vermittelte Reaktionen umfassen oxidative Arylkupplungen, Dehydrierung von Ketonen, Aziridinierung, Epoxidierung, Umlagerungen, Fragmentierungen und Entschützen von Dithianen.…”