- A Smooth and Practicable Azido-Iodination Reaction of Alkenes Based on IPy2BF4 and Me3SiN3
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The reaction of alkenes with IPy2BF4 and Me3SiN3 under the influence of BF3 · OEt2 provides a mild an efficient entry to vicinal azidoiodoalkanes. Besides the simplicity of the experimental protocol and the convenience found in the handling of the reagents, the use of stoichiometric amounts of the azide source is remarkable, and overrides the known and always troublesome dependence on large excesses of azide to accomplish this synthetically valuable transformation.
- Barluenga, Jose,Alvarez-Perez, Monica,Fananas, Francisco J.,Gonzalez, Jose M.
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- Stable polymer-bound iodine azide
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1,2-Azido-iodination of a wide range of alkenes under very mild conditions can be achieved by using a novel iodate(I) reagent, a stable and storable polymer-bound iodine azide, which is available in two steps (see scheme). Simple work-up and convenient use in automated parallel synthesis are important features of this polymer-bound reagent.
- Kirschning, Andreas,Monenschein, Holger,Schmeck, Carsten
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- A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach
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The reported flow-batch approach enables the easy preparation of 2H-azirines and their stereoselective transformation into highly functionalized NH-aziridines, starting from vinyl azides and organolithium compounds. The protocol has been developed using c
- Andresini, Michael,Degannaro, Leonardo,Luisi, Renzo
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supporting information
p. 203 - 209
(2021/02/26)
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- Self-Catalyzed Rapid Synthesis of N-Acylated/ N-Formylated α-Aminoketones and N-Hydroxymethylated Formamides from 3-Aryl-2 H-Azirines and 2-Me/Ph-3-Aryl-2 H-Azirines
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A rapid and effective method has been established for the synthesis of N-acylated α-aminoketone derivatives by the reaction of 3-aryl-2H-azirines and highly substituted 2-Me/Ph-3-aryl-2H-azirines with various carboxylic acids under ambient air within 10 min at room temperature. N-Trifluoroacetylated α-aminoketones with different substituents have been reported in the presence of trifluoroacetic acid. This protocol is equally effective to synthesize N-formylated α-aminoketone and N-hydroxymethylated formamide derivatives.
- De, Aramita,Majee, Adinath,Santra, Sougata,Zyryanov, Grigory V.
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supporting information
p. 3926 - 3930
(2020/07/14)
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- Photoswitchable Regiodivergent Azidation of Olefins with Sulfonium Iodate(I) Reagent
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Photoswitchable strategy for selective azidation of structurally diverse olefins under transition-metal-free conditions is reported. The unprecedented reactivity of trimethylsulfonium [bis(azido)iodate(I)] species under visible light allows radical azidooxygenation of the C═C πbond with distinctive selectivity. In the absence of visible light, the reaction proceeds through an ionic intermediate which led to complementary regioselectivity to provide α-alkyl azides. Mechanistic studies reveal that light-controlled regiodivergent azidation involving radical or an ionic pathway can be accomplished with exclusive regioselectivity.
- Rao, Dodla S.,Reddy, Thurpu R.,Gurawa, Aakanksha,Kumar, Manoj,Kashyap, Sudhir
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supporting information
p. 9990 - 9994
(2019/12/02)
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- Electrochemical regioselective azidoiodination of alkenes
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An efficient electrochemical approach to the vicinal iodoazides has been developed through constant current electrolysis of alkenes with NaN3and NaI in methanol. The reaction is proposed to proceed via a cyclic iodonium intermediate and thereby gives Markovnikov addition products exclusively.
- Yan, Wei-qing,Lin, Meng-ying,Little, R. Daniel,Zeng, Cheng-Chu
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p. 764 - 770
(2017/01/16)
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- Photoredox-catalysed redox-neutral trifluoromethylation of vinyl azides for the synthesis of α-trifluoromethylated ketones
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A redox-neutral, mild, and simple protocol is developed for the synthesis of α-trifluoromethylated ketones from vinyl azides under transition-metal-free conditions. In the presence of organic photoredox catalyst N-methyl-9-mesityl acridinium and sodium trifluoromethanesulfinate, a broad range of substituted vinyl azides were found to react smoothly upon visible-light irradiation, readily furnishing the corresponding products in satisfied yields.
- Qin, Hai-Tao,Wu, Shu-Wei,Liu, Jia-Li,Liu, Feng
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supporting information
p. 1696 - 1699
(2017/02/10)
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- Synthesis of α-Fluoroketones from Vinyl Azides and Mechanism Interrogation
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An efficient and mild fluorination of vinyl azides for the synthesis of α-fluoroketones is described. The mechanistic studies indicated that a single-electron transfer (SET) and a subsequent fluorine atom transfer process could be involved in the reaction.
- Wu, Shu-Wei,Liu, Feng
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supporting information
p. 3642 - 3645
(2016/08/16)
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- PIDA-I2 mediated direct vicinal difunctionalization of olefins: Iodoazidation, iodoetherification and iodoacyloxylation
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Iodinium cation (I+ or IOAc) was produced from the combination of phenyliodine diacetate (PIDA) and iodine. I+ facilitated the direct vicinal difunctionalization of olefins to α-azido, α-trideuteriomethoxy, α-2,2,2-trifluoroethoxy and α-acyloxy alkyl iodides via cation-π interaction at room temperature and under transition-metal free conditions.
- Achar, Tapas Kumar,Maiti, Saikat,Mal, Prasenjit
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p. 4654 - 4663
(2016/06/09)
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- Reactions of nitrile ylids with olefins gem-substituted with withdrawing groups
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In this study of 1,3-dipolar cycloadditions of nitrile ylids to olefin gem-substituted with withdrawing groups we have attempted to bring out the factors governing the diastereoselectivity of the reaction.Extensive studies have been made with allylic dipoles but few with propargyl dipoles.These reactions lead to stable pyrrol-1-ines in good yields. The adducts have been epimerized and, according to the method of generation of nitrile ylids, the isomerization of the dipoles or the dipolarophiles may occur. These facts have complicated the determination of the kinetic products.Owing to these difficulties, no interpretation of the results with perturbation theory has been attempted. - Keywords: stereochemistry / cycloaddition / 1,3-dipole / nitrile ylid / 1H-azirine / pyrrol-1-ine
- Perrocheau, Jacques,Danion-Bougot, Renee,Carrie, Robert
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p. 973 - 985
(2007/10/02)
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