Journal article

Publication year: 2017

Pages: 7093-7100

Journal: The Journal of Organic Chemistry

Volume number: 82

Issue number: 14

Open access status: Bronze

DOI Link: https://doi.org/10.1021/acs.joc.7b00557

Publisher: American Chemical Society

Abstract: 

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.

Harvard Citation style: Artaryan, A., Mardyukov, A., Kulbitski, K., Avigdori, I., Nisnevich, G., Schreiner, P., et al. (2017) Aliphatic C–H Bond Iodination by a N-Iodoamide and Isolation of an Elusive N-Amidyl Radical, The Journal of Organic Chemistry, 82(14), pp. 7093-7100. https://doi.org/10.1021/acs.joc.7b00557

APA Citation style: Artaryan, A., Mardyukov, A., Kulbitski, K., Avigdori, I., Nisnevich, G., Schreiner, P., & Gandelman, M. (2017). Aliphatic C–H Bond Iodination by a N-Iodoamide and Isolation of an Elusive N-Amidyl Radical. The Journal of Organic Chemistry. 82(14), 7093-7100. https://doi.org/10.1021/acs.joc.7b00557