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Dr. Pushpak Mizar Rebecca Niebuhr Matthew Hutchings Prof. Dr. Umar Farooq Prof. Dr. Thomas Wirth 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(5):1614-1617
An efficient thioamination of alkenes mediated by iodine(III) reagents is described. The use of different sulfur nucleophiles allows the flexible synthesis of 1,2‐aminothiols from alkenes. By employing chiral iodine(III) reagents, a stereoselective version of the thioamination protocol has also been developed. 相似文献
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Florence Malmedy Prof. Dr. Thomas Wirth 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(45):16072-16077
The first stereoselective version of an iodine(III)‐mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α‐arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid‐based iodine(III) reagents product selectivities of up to 73 % ee have been achieved. 相似文献
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Dr. Michael Brown Dr. Ravi Kumar Dr. Julia Rehbein Prof. Dr. Thomas Wirth 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(12):4030-4035
A stereoselective hypervalent iodine‐promoted oxidative rearrangement of 1,1‐disubstituted alkenes has been developed. This practically simple protocol provides access to enantioenriched α‐arylated ketones without the use of transition metals from readily accessible alkenes. 相似文献
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Dr. Alejandro Parra Dr. Silvia Reboredo 《Chemistry (Weinheim an der Bergstrasse, Germany)》2013,19(51):17244-17260
Chiral hypervalent iodine chemistry has been steadily increasing in importance in recent years. This review catalogues enantioselective transformations triggered by chiral hypervalent iodine(III/V) reagents, in stoichiometric or catalytic quantities, highlighting the different reactivities in terms of yield and enantioselectivity. Moreover, the synthesis of the most remarkable and successful catalysts has been illustrated in detail. 相似文献
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Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation 下载免费PDF全文
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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Flexible Stereoselective Functionalizations of Ketones through Umpolung with Hypervalent Iodine Reagents 下载免费PDF全文
Dr. Pushpak Mizar Prof. Dr. Thomas Wirth 《Angewandte Chemie (International ed. in English)》2014,53(23):5993-5997
The functionalization of carbonyl compounds in the α‐position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or “umpolung”, we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel retrosynthetic planning and rapid assembly of structures previously accessible only by multistep sequences. 相似文献
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Dr. Václav Matoušek Jiří Václavík Peter Hájek Julie Charpentier Zsófia E. Blastik Ewa Pietrasiak Alena Budinská Prof. Dr. Antonio Togni Dr. Petr Beier 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(1):417-424
A series of new hypervalent iodine reagents based on the 1,3‐dihydro‐3,3‐dimethyl‐1,2‐benziodoxole and 1,2‐benziodoxol‐3‐(1H)‐one scaffolds, which contain a functionalized tetrafluoroethyl group, have been prepared, characterized, and used in synthetic applications. Their corresponding electrophilic fluoroalkylation reactions with various sulfur, oxygen, phosphorus, and carbon‐centered nucleophiles afford products that feature a tetrafluoroethylene unit, which connects two functional moieties. A related λ3‐iodane that contains a fluorophore was shown to react with a cysteine derivative under mild conditions to give a thiol‐tagged product that is stable in the presence of excess thiol. Therefore, these new reagents show a significant potential for applications in chemical biology as tools for fast, irreversible, and selective thiol bioconjugation. 相似文献
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目前,微流控芯片分析系统中常用的检测方法有激光诱导荧光检测、质谱、化学发光、电化学和光度法等.其中应用最多的是激光诱导荧光检测器,但其所测样品大部分需要衍生. 相似文献
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Mohamed Elsherbini Bethan Winterson Haifa Alharbi Ana A. Folgueiras‐Amador Clina Gnot Thomas Wirth 《Angewandte Chemie (International ed. in English)》2019,58(29):9811-9815
An efficient and reliable electrochemical generator of hypervalent iodine reagents has been developed. In the anodic oxidation of iodoarenes to hypervalent iodine reagents under flow conditions, the use of electricity replaces hazardous and costly chemical oxidants. Unstable hypervalent iodine reagents can be prepared easily and coupled with different substrates to achieve oxidative transformations in high yields. The unstable, electrochemically generated reagents can also easily be transformed into classic bench‐stable hypervalent iodine reagents through ligand exchange. The combination of electrochemical and flow‐chemistry advantages largely improves the ecological footprint of the overall process compared to conventional approaches. 相似文献
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A direct and efficient method for the conversion of alkyl aryl ketones to imidazo[1,2‐α]pyridines has been developed based on initial formation of α‐organosulfonyloxy ketones and their subsequent cyclocondensation by 2‐aminopyridines in one‐pot conditions. 相似文献
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Dr. Huaiyuan Zhang Prof. Dr. Thomas Wirth 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(21):e202200181
Xanthene derivatives have broad applications in medicines, fluorescent probes, dyes, food additives, etc. Therefore, much attention was focused on developing the synthetic methods to prepare these compounds. Binaphthyl-based xanthene derivatives were prepared through the oxidation of BINOLs promoted by the hypervalent iodine reagent iodosylbenzene (PhIO). Nine-membered lactones were obtained through a similar oxidative reaction when iodoxybenzene (PhIO2) was used. Additionally, one-pot reactions of BINOLs, PhIO and nucleophiles such as alcohols and amines were also investigated to provide alkoxylated products and amides in good to excellent yields. 相似文献
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Nina Declas Prof. Dr. Jerome Waser 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(41):18413-18417
We report an Umpolung strategy of enol ethers to generate oxy-allyl cation equivalents based on the use of hypervalent iodine reagents. Under mild basic conditions, the addition of nucleophiles to aryloxy-substituted vinylbenziodoxolone (VBX) reagents, easily available in two steps from silyl alkynes, resulted in the stereoselective formation of substituted aryl enol ethers. The reaction was most efficient with phenols as nucleophiles, but preliminary results were also achieved for C- and N- nucleophiles. In absence of external nucleophiles, the 2-iodobenzoate group of the reagent was transferred. The obtained aryl enol ethers could then be transformed into α-difunctionalized ketones by oxidation. The described “allyl cation”-like reactivity contrast with the well-established “vinyl-cation” behavior of alkenyl iodonium salts. 相似文献
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Sermadurai Selvakumar Ryu Sakamoto Prof. Keiji Maruoka 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(19):6552-6555
Diastereoselective radical hydroacylation of chiral alkylidenemalonates with aliphatic aldehydes is realized by the combination of a hypervalent iodine(III) reagent and UV‐light irradiation. The reaction is initiated by the photolysis of hypervalent iodine(III) reagents under mild, metal‐free conditions, and is the first example of diastereoselective addition of acyl radicals to olefins to afford chiral ketones in a highly stereoselective fashion. The obtained optically active ketones are useful chiral synthons, as exemplified by the short formal synthesis of (?)‐methyleneolactocin. 相似文献
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We report an Umpolung strategy of enol ethers to generate oxy‐allyl cation equivalents based on the use of hypervalent iodine reagents. Under mild basic conditions, the addition of nucleophiles to aryloxy‐substituted vinylbenziodoxolone (VBX) reagents, easily available in two steps from silyl alkynes, resulted in the stereoselective formation of substituted aryl enol ethers. The reaction was most efficient with phenols as nucleophiles, but preliminary results were also achieved for C‐ and N‐ nucleophiles. In absence of external nucleophiles, the 2‐iodobenzoate group of the reagent was transferred. The obtained aryl enol ethers could then be transformed into α‐difunctionalized ketones by oxidation. The described “allyl cation”‐like reactivity contrast with the well‐established “vinyl‐cation” behavior of alkenyl iodonium salts. 相似文献
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