18589-27-0Relevant articles and documents
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Stone,Shechter
, p. 491,492 (1950)
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Aliphatic C-H Bond Iodination by a N-Iodoamide and Isolation of an Elusive N-Amidyl Radical
Artaryan, Alexander,Mardyukov, Artur,Kulbitski, Kseniya,Avigdori, Idan,Nisnevich, Gennady A.,Schreiner, Peter R.,Gandelman, Mark
, p. 7093 - 7100 (2017/07/26)
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.
NaIO4-KI-NaN3 as a new reagent system for C-H functionalization in hydrocarbons
Chouthaiwale, Pandurang V.,Suryavanshi, Gurunath,Sudalai, Arumugam
scheme or table, p. 6401 - 6403 (2009/04/06)
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.
Direct bromination and iodination of non-activated alkanes by hypohalite reagents
Montoro, Raul,Wirth, Thomas
, p. 1473 - 1478 (2007/10/03)
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.