- Aliphatic C-H Bond Iodination by a N-Iodoamide and Isolation of an Elusive N-Amidyl Radical
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Contrary to C-H chlorination and bromination, the direct iodination of alkanes represents a great challenge. We reveal a new N-iodoamide that is capable of a direct and efficient C-H bond iodination of various cyclic and acyclic alkanes providing iodoalkanes in good yields. This is the first use of N-iodoamide for C-H bond iodination. The method also works well for benzylic C-H bonds, thereby constituting the missing version of the Wohl-Ziegler iodination reaction. Mechanistic details were elucidated by DFT computations, and the N-centered radical derived from the used N-iodoamide, which is the key intermediate in this process, was matrix-isolated in a solid argon matrix and characterized by UV-vis as well as IR spectroscopy.
- Artaryan, Alexander,Mardyukov, Artur,Kulbitski, Kseniya,Avigdori, Idan,Nisnevich, Gennady A.,Schreiner, Peter R.,Gandelman, Mark
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p. 7093 - 7100
(2017/07/26)
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- PROCESS FOR THE PREPARATION OF N-IODOAMIDES
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The present invention provides new stable crystalline N-iodoamides - 1-iodo- 3,5,5-trimethylhydantoin (1-ITMH) and 3-iodo-4,4-dimethyl-2-oxazolidinone (IDMO). The present invention further provides a process for the preparation of organic iodides using N-iodoamides of this invention and recovery of the amide co-products from waste water.
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Paragraph 00291-00292
(2015/05/26)
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- NaIO4-KI-NaN3 as a new reagent system for C-H functionalization in hydrocarbons
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The NaIO4-KI-NaN3 combination has been found to be an efficient, reliable, and inexpensive reagent system for mono- and 1,2-difunctionalization of hydrocarbons via C-H bond activation to afford vicinal azido- and acetoxy iodinations of cyclic hydrocarbons.
- Chouthaiwale, Pandurang V.,Suryavanshi, Gurunath,Sudalai, Arumugam
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scheme or table
p. 6401 - 6403
(2009/04/06)
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- An efficient and facile hydroiodination of alkenes and alkynes PI using polymethylhydrosiloxane-iodine system
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A mild and efficient method has been developed for the synthesis of alkyl and alkenyl iodides from alkenes and alkynes using polymethylhydrosiloxane (PMHS) and iodine in chloroform at room temperature. The reagent system generates hydrogen iodide which regioselectively adds to the alkenes and alkynes. Copyright
- Das, Biswanath,Srinivas, Yallamalla,Holla, Harish,Narender, Ravirala
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p. 800 - 801
(2008/02/09)
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- Direct bromination and iodination of non-activated alkanes by hypohalite reagents
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The direct functionalisation of alkanes through bromination and iodination has been successfully achieved. The combination of stoichiometric mixtures of elemental halogen and sodium alkoxides leads to the formation of alkyl hypobromites and hypoiodites as reagents. The halogenation occurs without external photostimulation under thermal reaction conditions. Georg Thieme Verlag Stuttgart.
- Montoro, Raul,Wirth, Thomas
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p. 1473 - 1478
(2007/10/03)
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- New iodination reactions of saturated hydrocarbons
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Unactivated C-H bonds react with iodine when exposed to trimethylsilyl azide in the presence of a hypervalent iodine reagent or, alternatively, to aqueous H2O2, acetic anhydride, and sodium azide (see scheme). (Chemical Equation Presented).
- Barluenga, Jose,Campos-Gomez, Esther,Rodriguez, David,Gonzalez-Bobes, Francisco,Gonzalez, Jose M.
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p. 5851 - 5854
(2007/10/03)
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- Direct Iodination of Alkanes
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(Matrix presented) A cheap and efficient iodination of hydrocarbons can be achieved by generating tert-butyl hypoiodite from iodine and sodium tert-butoxide. The alkane is reactant and solvent, and this metal-free process provides a clean solution for their direct iodination.
- Montoro, Raul,Wirth, Thomas
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p. 4729 - 4731
(2007/10/03)
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- Activation of alkanes upon reaction with PhI(OAc)2-I2
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You can also choose from alkanes! Either mono- or bifunctional iodo derivatives can be prepared from alkanes (see scheme) in an efficient and selective manner by using PhI(OAc)2, I2, and an alcohol.
- Barluenga, Jose,Gonzalez-Bobes, Francisco,Gonzalez, Jose M.
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p. 2556 - 2558
(2007/10/03)
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- The first efficient iodination of unactivated aliphatic hydrocarbons
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No heavy metals, no enzymes, and a simple protocol: the direct iodination of aliphatic hydrocarbons, which has not been possible to date, can now be carried out in multiphase systems [see for example Eq. (l)]. In situ generated tetraiodomethane serves as a key intermediate in this selective radical chain reaction initiated by a single electron transfer. This room-temperature, efficient transformation is highly regioselective, easy to work-up, and hence widely applicable.
- Schreiner, Peter R.,Lauenstein, Oliver,Butova, Ekaterina D.,Fokin, Andrey A.
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p. 2786 - 2788
(2007/10/03)
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- Regeneration and recovery of hydriodic acid after reduction of polyols to fuels
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Polyols such as sorbitol, now directly available from biomass carbohydrates, are reduced by hydriodic acid (HI) to hydrocarbon fuels (80%) with some alkyl halide (20%) according to a new process (eq 1). Incipient iodine (I2) is reduced and returned to hydriodic acid (HI) in situ by the simultaneous use of either phosphorous acid (H3PO3) or hypophosphorous acid (H3PO2) rather than elemental red phosphorus. The acid mixture can be reused many times. Eventually, HI must be recovered from the ever-increasing amount of phosphoric acid and water in the mixture. The recovery process consists of two to three distillation steps but for safety reasons combines an initial air oxidation of any excess H3PO3 to H3PO4. 31P NMR conveniently monitors phosphorus moieties. Less than a mmol/L of HI remains in the final phosphoric acid pot residue. This coupled redox combination of reducing acids may allow other industrial uses of otherwise expensive HI at the lesser expense of H3PO3 or H3PO2, either of which also provide the benefit of a homogeneous system.
- Michael Robinson,Herndon, Paul T.,Holland, Preston L.,Marrufo, Laura D.
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p. 352 - 356
(2013/09/08)
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