This account describes the development of organosulfonyloxy-substituted iodine(III) and iodine(V) benziodoxole derived reagents, which are thermally stable compounds with useful reactivity patterns. Iodine(III) benziodoxoles and pseudobenziodoxoles are powerful electrophiles and mild oxidants toward various unsaturated compounds. In particular, pseudocyclic benziodoxole-derived triflate (IBA-OTf) is an efficient reagent for oxidative heteroannulation reactions. Aldoximes react with nitriles in the presence of IBA-OTf at room temperature to give 1,2,4-oxadiazoles in high yields. Moreover, IBA-triflate is used as a catalyst in oxidative heteroannulations with m-chloroperoxybenzoic acid as the terminal oxidant. The iodine(V) benziodoxole derived tosylates, DMP-tosylate and IBX-tosylate, are superior oxidants for the oxidation of structurally diverse, synthetically useful alcohols, utilized as key precursors in the total syntheses of polyketide antibiotics and terpenes. And finally, the most powerful hypervalent iodine(V) oxidant, 2-iodoxybenzoic acid ditriflate (IBX·2HOTf), is prepared by treatment of IBX with trifluoromethanesulfonic acid. According to the X-ray data, the I–OTf bonds in IBX-ditriflate have ionic character, leading to the high reactivity of this reagent in various oxidations. In particular, IBX-ditriflate can oxidize polyfluorinated primary alcohols, which are generally extremely resistant to oxidation. 1 Introduction 2 Iodine(III) Benziodoxole Based Organosulfonates 3 Pseudocyclic Iodine(III) Benziodoxole Triflate (IBA-triflate) 4 Pseudocyclic Iodine(III) Benziodoxole Tosylates 5 Iodine(V) Benziodoxole Derived Tosylates 6 Iodine(V) Benziodoxole Derived Triflate (IBX-ditriflate) 7 Conclusions

中文翻译：

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苯并恶醇衍生的有机磺酸盐：最强的高价碘亲电试剂和氧化剂

该帐户描述了有机磺酰氧基取代的碘 (III) 和碘 (V) 苯并恶醇衍生试剂的开发，它们是具有有用反应模式的热稳定化合物。碘 (III) 苯并氧杂环戊烷和假苯并氧杂环戊烷是强大的亲电子试剂和对各种不饱和化合物的温和氧化剂。特别是，伪环苯并氧杂环戊烷衍生的三氟甲磺酸酯 (IBA-OTf) 是氧化杂环化反应的有效试剂。在 IBA-OTf 存在下，醛肟在室温下与腈反应，以高产率得到 1,2,4-恶二唑。此外，IBA-三氟甲磺酸酯在以间氯过氧苯甲酸为末端氧化剂的氧化杂环化反应中用作催化剂。碘 (V) 苯并恶醇衍生的甲苯磺酸盐、DMP-甲苯磺酸盐和 IBX-甲苯磺酸盐，是用于氧化结构多样、合成有用的醇，用作聚酮化合物抗生素和萜烯全合成的关键前体。最后，通过用三氟甲磺酸处理IBX制备了最强的高价碘（V）氧化剂，2-碘氧基苯甲酸二三氟甲磺酸酯（IBX·2HOTf）。根据 X 射线数据，IBX-二三氟甲磺酸酯中的 I-OTf 键具有离子特性，导致该试剂在各种氧化中具有高反应性。特别是，IBX-二三氟甲磺酸酯可以氧化多氟伯醇，其通常具有极强的抗氧化性。