1556-18-9Relevant articles and documents
The first efficient iodination of unactivated aliphatic hydrocarbons
Schreiner, Peter R.,Lauenstein, Oliver,Butova, Ekaterina D.,Fokin, Andrey A.
, p. 2786 - 2788 (1999)
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.
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Kornblum,Teitelbaum
, p. 3076 (1952)
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First examples of superelectrophile initiated iodination of alkanes and cycloalkanes
Akhrem, Irena,Orlinkov, Alexander,Vitt, Sergei,Chistyakov, Anatolii
, p. 1333 - 1335 (2002)
Direct iodination of alkanes and cycloalkanes in the presence of superelectrophiles has been accomplished for the first time. The reactions of saturated hydrocarbons with I2 in the presence of CCl4·2AlI3 at -20°C afforded monoiodides in good yields and selectivities.
A CONVENIENT METHOD FOR THE ADDITION OF HI TO UNSATURATED HYDROCARBONS USING I2 ON Al2O3
Stewart, Lyman J.,Gray, Donna,Pagni, Richard M.,Kabalka, George W.
, p. 4497 - 4498 (1987)
Iodine reacts, under mild conditions, with hydroxyl groups on the surface of alumina to form HI which readily adds to unsaturated hydrocarbons to form alkyl and vinyl iodides.
Manganese-Mediated Direct Functionalization of Hantzsch Esters with Alkyl Iodides via an Aromatization-Dearomatization Strategy
Liu, Xian-Guan,Dong, Ci-Shuang,Li, Fei,Zhang, Bo
supporting information, p. 4002 - 4007 (2021/05/26)
We report, for the first time, manganese-mediated direct functionalization of the Hantzsch esters with readily accessible alkyl iodides through an aromatization-dearomatization strategy. Applying this protocol, a library of valuable 4-alkyl-1,4-dihydropyridines were facilely afforded in good yields. This simple and practical reaction proceeds under visible-light irradiation at room temperature and displays high functional-group compatibility. Additionally, the method is applicable for gram-scale synthesis and late-stage functionalization of complex molecules.
Visible-Light-Mediated C-I Difluoroallylation with an α-Aminoalkyl Radical as a Mediator
Yue, Fuyang,Dong, Jianyang,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 7306 - 7310 (2021/10/01)
Herein, we report a protocol for direct visible-light-mediated C-I difluoroallylation reactions of α-trifluoromethyl arylalkenes with alkyl iodides at room temperature with an α-aminoalkyl radical as a mediator. The protocol permits efficient functionalization of various α-trifluoromethyl arylalkenes with cyclic and acyclic primary, secondary, and tertiary alkyl iodides and is scalable to the gram level. This mild protocol uses an inexpensive mediator and is suitable for late-stage functionalization of complex natural products and drugs.