Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

Radical Arylation of Anilines and Pyrroles via Aryldiazotates

Radical Arylation of Anilines and Pyrroles via Aryldiazotates
Markus R. Heinrich, Timothy Clark, Josefa Hofmann, Eva Gans
The radical arylation of anilines and pyrroles can be achieved under transition-metal- and catalyst-free conditions by using aryldiazotates in strongly alkaline aqueous solutions. The aryldiazotates act as protected diazonium ions, which do not undergo azo coupling with electron-rich aromatic substrates, but can still serve as an aryl radical source at slightly elevated temperatures. Based on an improved preparation of aryldiazotates in aqueous solution, homolytic aromatic substitutions of anilines and pyrroles were conducted with good overall yields and high regioselectivity. Moreover, DFT calculations provided further mechanistic insights. It's all in the preparation! Based on an improved preparation of aryldiazotates, the arylation of anilines and 1-substituted pyrroles could be achieved under transition-metal- and catalyst-free conditions (see scheme). By combining experimental and computational results, this study gives insights into the particular features of the underlying reaction mechanism.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701429

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