Issue 13, 2021

Azo synthesis meets molecular iodine catalysis

Abstract

A metal-free synthetic protocol for azo compound formation by the direct oxidation of hydrazine HN–NH bonds to azo group functionality catalyzed by molecular iodine is disclosed. The strengths of this reactivity include rapid reaction times, low catalyst loadings, use of ambient dioxygen as a stoichiometric oxidant, and ease of experimental set-up and azo product isolation. Mechanistic studies and density functional theory computations offering insight into this reactivity, as well as the events leading to azo group formation are presented. Collectively, this study expands the potential of main-group element iodine as an inexpensive catalyst, while delivering a useful transformation for forming azo compounds.

Graphical abstract: Azo synthesis meets molecular iodine catalysis

Supplementary files

Article information

Article type
Paper
Submitted
15 jan 2021
Accepted
02 fev 2021
First published
11 fev 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 7251-7256

Azo synthesis meets molecular iodine catalysis

R. Rowshanpour and T. Dudding, RSC Adv., 2021, 11, 7251 DOI: 10.1039/D1RA00369K

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