Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Aliphatic C–H Bond Iodination by a N-Iodoamide and Isolation of an Elusive N-Amidyl Radical

Aliphatic C–H Bond Iodination by a N-Iodoamide and Isolation of an Elusive N-Amidyl Radical
Artur Mardyukov, Kseniya Kulbitski, Idan Avigdori, Peter R. Schreiner, Mark Gandelman, Alexander Artaryan, Gennady A. Nisnevich
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00557

DOI: 10.1021/acs.joc.7b00557

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