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The ring and I: Hypervalent iodine compounds avoid the issues of toxicity or complicated ligands of many transition-metal-based systems. A highly enantioselective oxyamination of alkenes with N-sulfonyl ureas employing chiral, lactic acid-based hypervalent iodine reagents gives a facile synthesis of enantiomerically pure 2-arylproline derivatives for the first time. 相似文献
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Niedermann K Früh N Senn R Czarniecki B Verel R Togni A 《Angewandte Chemie (International ed. in English)》2012,51(26):6511-6515
Effective CF(3) transfer: Various electron-rich nitrogen heterocycles (pyrazoles, triazoles, and tetrazoles) can be directly N-trifluoromethylated by a hypervalent iodine reagent in an efficient manner. The optimized procedure, which includes an in situ silylation of the substrate followed by an acid-catalyzed CF(3) transfer, provides ready access to a series of new and previously challenging or inaccessible NCF(3) compounds. 相似文献
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Alexey Y. Koposov 《Tetrahedron letters》2004,45(13):2719-2721
Amides of 2-iodoxybenzenesulfonic acid were prepared by the dioxirane oxidation of the corresponding 2-iodobenzenesulfamides and isolated as stable, microcrystalline products. These new representatives of the pseudocyclic hypervalent iodine compounds can selectively oxidize benzylic alcohols to aldehydes. 相似文献
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About 30?% of the world's iodine production comes from the Chiba area in Japan, shown in the background of the picture (Map data (?) 2012 ZENRIN Imagery (?) 2012 TerraMetrics). Enantiomerically pure hypervalent iodine compounds are the key for metal-free, highly stereoselective oxyaminations of alkenes. In their Communication on page?3462?ff., T. Wirth and U. Farid report the use of the reaction for the facile synthesis of 2-arylprolinols. 相似文献
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Harayama Y Yoshida M Kamimura D Wada Y Kita Y 《Chemistry (Weinheim an der Bergstrasse, Germany)》2006,12(18):4893-4899
Hypervalent iodine(III) reagents are readily available, easy to handle, and have a low toxicity and similar reactivities to those of heavy metal reagents, and hence they are used for various oxidative reactions. The oxidative cleavage of alkynes or carbonyl compounds by using bis(trifluoroacetoxy)iodo(III) pentafluorobenzene (C(6)F(5)I(OCOCF(3))(2)) has been reported. Herein, the efficient direct synthesis of N,O-acetal compounds as key intermediates of discorhabdin A, by the oxidative fragmentation reaction of alpha-amino acids or beta-amino alcohols by using C(6)F(5)I(OCOCF(3))(2), is described. 相似文献
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Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation
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Yifan Li Dr. Durga Prasad Hari Maria Victoria Vita Prof. Dr. Jerome Waser 《Angewandte Chemie (International ed. in English)》2016,55(14):4436-4454
Hypervalent iodine compounds are privileged reagents in organic synthesis because of their exceptional reactivity. Among these compounds, cyclic derivatives stand apart because of their enhanced stability. They have been widely used as oxidants, but their potential for functional‐group transfer has only begun to be investigated recently. The use of benziodoxol(on)es for trifluoromethylation (Togni's reagents) is already widely recognized, but other transformations have also attracted strong interest recently. In this Review, the development in the area since 2011 will be presented. After a short summary of synthetic methods to prepare benziodoxol(on)e reagents, their use to construct carbon–heteroatom and carbon–carbon bonds will be presented. In particular, the introduction of alkynes by using ethynylbenziodoxol(on)e (EBX) reagents has been highly successful. Breakthroughs in the introduction of alkoxy, azido, difluoromethyl, and cyano groups will also be described. 相似文献
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An efficient method for direct α-sulfonyloxylation of various sterically hindered 1,3-dicarbonyl compounds has been developed under mild reaction conditions. The yields of desired products is up to 90% and a plausible mechanism was accordingly proposed. 相似文献